chartering a sailboat in the caribbean

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Discover Paradise in St Vincent & the Grenadines

Premier Sailing School offered weekly

Bareboat or with a Captain - the choice is yours !

Welcome to Barefoot Yacht Charters

The Barefoot Lifestyle – No Shoes, No Stress, No Mess

Neptune Fleet

Discover the epitome of seafaring indulgence with Barefoot Yachts’ Neptune fleet, meticulously outfitted and maintained for discerning adventurers. Our luxury comfort yachts redefine relaxation, boasting opulent amenities and spacious layouts, ensuring an unrivaled at-anchor experience. Immerse yourself in tranquility and luxury as you cruise the pristine waters of the Grenadines. On the other hand, our luxury performance fleet stands as a testament to superior sailing, designed to thrill and delight enthusiasts seeking exhilarating voyages. Sail with precision, power, and grace, embracing the wind and waves like never before, reveling in the exciting sailing conditions for which the Grenadines are famous. Barefoot Yachts, a boutique family-owned charter company, invites you to savor the finest in nautical luxury.

Viewfinder 2020 Bali 4.1

Ulysses Lagoon 42

Sonhos Bali 4.4

Sonder Seawind 1260

Inconceivable Leopard 50

Hearts Desire Lagoon 46

Catara NEEL 43

AONYX O-Yacht 45

Navigator fleet.

Embark on a cost-effective voyage without compromising luxury aboard Barefoot Yachts’ Navigator fleet, featuring 5-year-old and older sailing yachts. Choose from our distinct categories: luxury comfort yachts, tailored for an idyllic at-anchor escape with opulent amenities, or luxury performance yachts, finely tuned to deliver thrilling and memorable sailing journeys. Experience the blend of affordability and elegance as you navigate the beautiful waters, soaking in the sunsets and salty breeze. Barefoot Yachts, a cherished boutique family-owned charter company, invites you to relish an unmatched balance of economy and indulgence on the high seas.

Willow Dew Lagoon 39

Pelican Pete Sun Odyssey 34

Lady Di Oceanis 41

Inordinate Venezia 42

Betty Blue Beneteau 50

Fully crewed yachts.

Experience unparalleled opulence aboard A Barefoot Yachts’ fully crewed private luxury yacht charter, where desires are effortlessly met by an attentive crew dedicated to pampering guests with first-class service. Indulge in delectable gourmet meals prepared by your private chef and revel in the freedom to sail on your schedule. With over 32 years of navigating the Grenadines, Barefoot Yachts offers a unique understanding of the region, ensuring an exclusive journey through these breathtaking waters, enriched by their expert insight into the cruising grounds and the vibrant local culture.

Rob Roy CATANA 531

Racing fleet.

Embark on a sailing adventure of a lifetime with Barefoot Yachts’ race charters in the Caribbean! Picture yourself on the tiller of a professionally maintained, high-performance sailboat, cutting through the azure waters of the Caribbean. Experience the exhilaration of competitive racing and join the ranks of international sailors, embracing the thrill of challenging race courses set amidst the incredible beautiful of these iconic islands. Revel in post-race festivities under starlit Caribbean skies, sipping fine local rums and dancing to the rhythm of this vibrant paradise. Unleash your inner competitive sailor and experience some of the best grand prix racing events in the world, with Barefoot Yachts.

HAPPY Melges 20

SMILE (#212) Melges 20

SALT FISH J 24

GONE C&C 30

SEAPLANE Melges 32

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The Barefoot Lifestyle

At Barefoot, our philosophy is simple and our lifestyle is sweet. Through our commitment to you experiencing your ultimate vacation, clean sailing, our use of locally produced organic provisioning and our responsible operating practices, we hope to protect and enhance your experience while improving the world we share with all living things.

Driftwood Restaurant/Bar

Driftwood Restaurant offers Mediterranean cuisine with a Caribbean flair, a stunning seaward view of Blue Lagoon and an intimate, air-conditioned lounge bar. We specialize in local, organically grown fruits and veggies.

Caribbean Bareboat Sailing Charter Videos

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CARIBBEAN YACHT CHARTERS

1240 boats available for bareboat or crewed charter

Yachts from professional fleet operators in Caribbean

Free cancellation of reservation without obligations within 4 days

Most popular boats For rent in CARIBBEAN

Helia 44 - 4 + 2 cab. (2018)

Leopard 45 (2023)

EXCESS 11 (4 CAB) (2023)

SABA 50 (2018)

Dufour 412 GL (2018)

OCEANIS 41.1 (2019)

Lagoon 52 F - 6 + 2 cab. (2020)

Fountaine Pajot Elba 45 - 3 cab. (2023)

Bali Catspace (2023)

Fountaine Pajot Aura 51 - 6 cab (2023)

Top destinations in caribbean for boat rental.

443 boats for charter

from £1,233 per week

256 boats for charter

from £1,041 per week

US VIRGIN ISLANDS (USVI)

131 boats for charter

from £1,254 per week

THE BAHAMAS

128 boats for charter

from £1,431 per week

95 boats for charter

from £1,156 per week

79 boats for charter

from £1,044 per week

• Guadeloupe 74 boats in Guadeloupe 74
• Antigua 48 boats in Antigua 48
• St. Vincent 38 boats in St. Vincent 38
• St. Lucia 28 boats in St. Lucia 28
• Puerto Rico 6 boats in Puerto Rico 6

Types of boats available for rent in Caribbean

Catamaran charter

964 catamarans available for rent in Caribbean, form €1,229 for 1 week charter. Ideal option for group of friends or family vacation.

Sailboat charter

There are 210 sailboats available for charter in Caribbean, prices start from €1,189 per week. Most budget friendly option for a vacation.

Power boat charter

37 powerboats available in Caribbean for rent, starting from €1,650 per week. Bareboat or crewed options available for sailing vacations.

Trimaran charter

11 trimarans available for rent in Caribbean, with prices from €3,395 per week. Great option for skippers looking for performance boats.

Gulets charter

Currently not available for charter in this country. Check other boat types.

Houseboat charter

Yacht charter types available in Caribbean

Bareboat charter, crewed yachts, by the cabin charter, skippered boats, cost of boat rental in caribbean.

Average yacht charter cost in Caribbean starts from £3,596 per week. Graphic below represents fluctuation of charter prices in Caribbean during the year, based on a sample of 50 boats ranging from 40 to 50-foot. This graphic shows months with lowest prices during the year as well high season when prices are above average. Before booking the boat at lowest rate, please check sailing conditions as usually best prices are during off season.

Caribbean Yacht Charter Reviews with 12knots

Steven Castle

United States

“Easiest experience I have had”

As I was searching for a charter, I found 12 Knot via Google search. From initial finding to securing a great boat, was easiest experience I have had in bareboat chartering. Julia was great to work with and bridge with Marian contact when my arrival …

Ven Dobrinov

“Everything was perfect!”

Dear Grigory, Everything was perfect! Thank you :) Please see the attached photo.

“Great experience”

Great experience! The boat was in a good shape. Flawless communication with 12 Knots and the base.

Adrian Grigorof

“Everything was arranged as planned”

We chartered 2 sailing catamarans for a 10 day USVI/BVI vacation and everything was arranged as planned. Good communication, good service, no surprises. The boats were in perfect shape and we had a great time.

Ghislain Devouton

“12 knots was great organizing my cruise”

12 knots was great organizing my cruise in French Polynesia. They answered all my questions along the way and made it easy.

John Farmer

“Very good job!”

12 Knots did a very good job inspite of the fact that some materials were in French.

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Sailing Around Windward and Leeward Islands of the Caribbean

The  Caribbean covers a huge region of widely spread islands 2,000 miles (3,218 km) long.

The larger ones have become sovereign countries with broad range of amenities for sailors, while the smaller ones still preserve its untouched rural charm and tranquility.

From the western tip of Cuba to the Leewards in the east, then south to the top of South America and along Venezuela’s north coast – this chain of islands has created a hook-like shape around the Caribbean Sea. Location like this is always an enticing bait for sailing - perfect climate and  array of diverse cultures, customs, cuisines and experiences, water sports and an unlimited number of other attractions.

Planning sailing vacations in Caribbean, you may wish to consider these groupings of the islands as points of your itinerary, as they contain many popular cruising areas and harbor stops. There is no doubt that in the scope of Caribbean bareboat or skippered yacht charters  both groups have their charms and countless reasons to explore, which definitely makes it a great sailing destination.

Caribbean yacht rentals

12 Knots offers eleven yacht charter bases in the Caribbean region, each with unique individual character, providing sailing experience for everyone, from a novice to an experienced sailor. This region comprises more than 700 hundred islands and islets, so you can choose Caribbean sailing vacations with shot and easy hops or more challenging passages.

Taking Caribbean sailing vacations, you will find warm and steady trade winds in picturesque surroundings; discover plenty of great bars and authentic cuisine!

It’s up to you, choosing between the Leeward Caribbean islands with short and easy hops with line-of-sight sailing and the Windward with more challenging open water passages. Wherever you go, you will return home relaxed, refreshed and ready to start planning your next Caribbean sailing adventure.

The Windward islands

Windward Islands located at the southern end of the Caribbean island chain and stretch for over 300 miles to the south-eastern end of the Caribbean Sea. The Windward Islands are simply called so due to their position as they are exposed to the northeast trade winds. For experienced sailors, it can be right choice to sail among the four main islands: Martinique, St. Lucia, St. Vincent and Grenada. They lay far apart each other allowing open ocean sailing and while steady easterly trade winds, make passages north or south easy. With constant 12 to 25 knots wind, Caribbean sailing is among best in the world. Night anchorages in peaceful and protected areas give sailors freedom to explore and soak up British and French island culture. The islands of St. Lucia, St. Vincent and Grenada  were British colonies until they gained independence during the 1970s. Martinique is still an overseas department of France.

The climate of the Windward Islands is definitely a marine one.

When tropical heat reaches its peak, steady trade winds and daily sea breezes come to rescue.

Typically, dry and wet seasons go hand in hand here. Although the priority of more rainfalls is given to the eastern side of the islands mainly due to the prevailing north-east trade winds there.

The islands east of Puerto Rico were called “Windward Islands” by the Spanish, while the islands south of Puerto Rico were named as “Leewards “. And Dominica positions itself right on the border line between the Windward and the Leeward Islands.

Long time ago some of the islands used to be French colonies, subsequently gained its name as The French Antilles.

The population of the Windward Islands is mostly of African origin, with some exceptions of Chinese and Caucasians. The present day Windward Islands will welcome tourists with upscale resorts, stunning beaches and pleasant sunny weather.

After cruising through the Windward Islands, you may wish to set sails to the Leeward Islands.

The Leeward islands

The Leeward islands are located on the eastern edge of the Caribbean Sea and form the northeastern boundary between Caribbean and Atlantic Ocean, extending from Puerto Rico to the Windward Islands, forming part of the Lesser Antilles chain.

Although 700 miles long stretch of these magnificent isles mostly constitute the whole body of the Leewards, it provides the abundance of enjoyment: quaint fishing spots, ancient ruins and delicious authentic cuisine.

Blessed with balmy temperatures all around the year, The Leeward Islands are called leeward because they're away from the wind or downwind (in the "lee"). Leeward group of Caribbean islands includes: the U.S. Virgin Islands, the British Virgin Islands, Anguilla, Saint Martin, Saint-Barthelemy, Saba, Sint Eustatius, Saint Kitts, Nevis, Barbuda, Antiqua, Redonda, Montserrat and Guadeloupe.

One of two "sister islands", St Kitts and Nevis, provides a brilliant Caribbean experience, from their picture-perfect beaches and volcanic mountains to friendly locals and layers of history to explore. For the water sport lovers, there are numerous aquatic activities that include fishing, diving, windsurfing and surfing.

St.Kitts and Nevis

Switch from sailing to inland for a change and St.Kitts and Nevis will deliver the most exceptional hiking in the Caribbean. The dormant volcano of Mount Liamuiga is considered to be the toughest to climb. And with the experienced guide you may even try to descend in its crater!

The unspoiled landscape of dry littoral forest and rainforest will present memorable show of fauna and flora. Many plants are of culinary and medical use, and some even used in black magic, as informative guides would point out its botanical value.

The wild life-lovers will not be disappointed with variety of different types of exotic animals.

Actually, the Great Salt Pond has become famous for its largest habitat of green velvet monkeys.

St. Kitts and Nevis will keep you captivated with majestic view of huge conical shells, remains of old sugar mills, along with some other plantation ruins, built in the 18 th century.

Back to water activities, and tourists will be pleased with what these two island can offer: deep-water fishing, snorkeling, scuba diving and more.

Then in order to satisfy your growing appetite visit two popular restaurants: Carambola and the Shipwreck Bar and Grill to enjoy its delicious local meals.

A yacht charter in the Caribbean Leeward Islands offers sailors an unrivalled remarkable experience. Enjoy tropical landscapes, pristine palm-lined beaches and azure waters — all the joys of marine life.

Sailing over the Leeward Islands may have all the pleasures to offer: the Tropical rainforests, glittering coral reefs, and luxury sand beaches. That’s probably why most of the known tourist resorts on these islands play a critical role in their economy, as do banking and fishing. Many of them also rely on their status as a tax haven to promote offshore financial services as a source of government revenue. But there is much more to discover in the Leeward Islands. These Caribbean islands provide great variety of yachts for charter and pleasant sailing vacations. Most of the Leeward Islands are located close to each other with moderate winds from 10 to 15 knots and rather low wavers. BVI is the most popular area for Caribbean charters either bareboat or luxury crewed vacations. This is the right place for the novice sailor’s easy passages in line-of-sight sailing.

The climate of the Caribbean Leeward Islands can be described as tropical, but much drier than in Windward Islands. Though the climate does vary from island to island and can even be different in different parts of the same island. Rainfall increases with elevation and in more southerly latitudes. In some cases trade winds look like refreshing tonic to the tropical heat. There is minor seasonal variation, although the second half of the year, the wet season, is slightly warmer and rainier. The best time for sailing in the Caribbean may be the first half of the year. At this time the temperatures usually range between 81°F (27°C) and 95°F(35°C). Annual rainfall averages about 40 to 50 inches (1016 to 1270 mm). Keep in mind, that nearly every island had been severely damaged by hurricane activity in its recent history.

English is the most widespread language all around the islands, plus many of the people speak French and Dutch on the St Martin Island. Both English-based and French-based Creole are also spoken. The prevailing currency is The East Caribbean dollar. But St Martin is odd man out again, circulating the Netherlands Antilles guilder in the Dutch area and the Euro in the French region. Nevertheless, the US dollar is widely accepted throughout the islands.

If you eager to take part in sporting activities, then you may be pleased to know that cricket is widely played and followed in the former British territories. Besides, as in the rest of the Caribbean, music is also always a big part of local life. Enjoy the magical sounds of calypso, soca, steelpan, reggae, salsa and jazz — all of the mentioned has their adherents.

During your Caribbean yacht charter, you may wish to participate in some major holiday celebrations, including the St Kitts Christmas, New Year carnaval, the annual music festival, as well as Anguilla’s Emancipation Day and Culturama festival on August 1st.

The culture of the Leeward Islands is varied by different influences, including French, Dutch and West Indian. Due to that sailing around the Leeward Islands provides a wonderful choice of cuisine and some great restaurants to satisfy your affection for the finest dishes. By the way, the island of Anguilla offers true gastronomic feasts. When sailing in the Caribbean Leeward Islands, be sure to try freshly caught lobsters with a glass of wine.

Sailing the Caribbean With 12 Knots

So, while planning a Caribbean charter it is highly recommended to decide on how many islands you would like to visit in a given time frame. Research Caribbean boat rentals and determine which island you would like to have as a starting base. Then you can plan an itinerary for the week or ten days, taking into consideration distances between the islands and activities you would like to have, like island tracking, scuba diving, snorkeling, volcano hiking, or even shopping.

12 Knots team will give you plenty of useful information not only on the bareboat charter in Caribbean, but also itineraries, places of interest and peculiarities of each island.

Taking a yacht charter in the Caribbean is just a perfect combination of sailing and relaxation, authentic culture and a range of water sport activities. In a few words, this area may always offer something for everyone in these amazing islands’ surrounding.

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Sail the Caribbean

• Location Guide
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Color and Contrast: the Complete Sailboat Vacation

Simply the perfect place to take a bareboat or skippered sailing holiday. Such a diverse collection of islands dotting the clear blue sea, each with its own unique appeal. Local cultures that fascinate and entertain, offering a welcome that keeps charterers returning to these waters year after year. With its 7,000 Islands and 28 Island nations, reliable trade winds and long sailing season, the Caribbean is a region that offers an endless amount of holiday enjoyment.

At Sail Connections, we work with all the best charter operators in the Caribbean, sorting through all the available boats and presenting all the best options to suit your vacation plans. Some of our operators offer extra services that are unique to their destinations. We personalize your proposal and give you the benefit of our knowledge and local contacts, to deliver a fabulous sailing holiday wherever there's a boat to charter in the Caribbean. 

Charter Sailing in the Caribbean

The Caribbean's numerous islands give you so many fabulous places to explore, so many diverse cultures to experience, that the permutations for planning a sailing charter are simply too numerous to list. The sailing distances between territories can be very short, and there are countless yacht charter bases scattered across the region. That opens the door to all manner of opportunities – from a seven-day sail around one distinct island nation to a multi-week one-way charter that takes in a wide variety of cultures and geographical features.

The Caribbean yacht charter season is busy from November through July. The peak season is mid-December to March, when winter escapees from North America and Europe arrive in their greatest numbers.

The hurricane season arrives late July and can last until early October, although storms here are rare and tend to deflect northwards towards the USA rather than hit the Caribbean. These months have their advantages in that they are the least costly for chartering, particularly in the British Virgin Islands. At that time of year it is in fact more likely to encounter light winds than it is storms.

As with many yacht charter locations, the shoulder season can be the best time to charter a yacht. In the Carribean that's from April to July. There are less shore-based visitors then, yet you can expect settled and sunny weather with warm, steady breezes prevailing.

We have access to over 30 charter bases in the region, from where you can take a sailboat vacation like no other. We select from the best boats available and guide you into the ideal sailing adventure that matches your interests and level of experience. The sailing options here are just about endless. Hopefully these pages will help you on your way to your much-anticipated Caribbean sailing holiday.

Regional Map of the Main Charter Sailing Areas

A one-way cruise: martinique to grenada, there are quite simply countless itinerary options for sailing the caribbean. for many charterers a downwind cruise offers the crew conditions for maximum enjoyment. so here's a sample north to south course plan that gives you the prevailing breeze abaft. .

Waterfront at Fort de France, Martinique's largest town

Sailing from Martinique to Grenanda you can expect winds primarily from the northeast, especially around peak season either side of Christmas. Sailing this course involves short stretches of open water, with a stiff and steady breeze on your aft quarter. That makes for quick passages with most enjoyable sailing to a choice of Islands, whether it be for a lunch stop and a snorkel, or an overnight stay.

The eastern Caribbean islands that form a distinctive arc on the map are collectively the Lesser Antilles, a mixture of soverign states and territories governed by various powers. A trip along some of this chain exposes the voyager to a wide variety of cultures and customs in places that all sit in the idyllic picture-postcard surroundings of the movies and travel brochures. 

Starting in Martinique and sailing south, you are exploring the Windward Island group of the Antilles.

Wildlife viewing at its finest in the Tobago Cays

Like most of this group, Martinique was orginally colonised by France, and French flair is still in evidence there today. Martinique offers excellent on-shore facilities for the visitor, and is a popular base for boat charters. The island is mountainous, but with plenty of white sandy beaches to enjoy, especially in the south.

The next island is St Lucia. It's some 30 nautical miles to Rodney Bay on St Lucia's northwest, so to get there requires an early start. There are several top spots to visit down the island's sheltered western coast. Take time out to investigate Les Deux Pitons.

Another long but relaxing sail to St Vincent and the Grenadines, so-named because of their joint French and British colonial history. St Vincent has its Blue Lagoon that you'll probably overnight in, while the Grenadines island group, some of which confusingly belong to Grenada, provide numerous anchoring options.

Happy charterers enjoying their time ashore in the Grenadines

The Grenadines stretch all the way to Grenada, your final port of call, making this part of the voyage very convenient for a leisurely sail. Call in at one of the uninhabited Tobago cays for a real taste of desert island living, if only for a few hours.

Once offshore Carriacou you are in Grenadan territory. Grenada, like St Lucia & St Vincent and the Grenadines, is now an independent member of the British Commonwealth, but with historical French influence. This is the 'Island of Spice' where nutmeg and mace production are important to the economy. As is tourism, and there is plenty to entertain you before concluding your vacation and departing these fabulous sailing waters.

Once you have experienced all the pleasures of sailing the Caribbean, chances are you'll be back one day for more.

The Best Caribbean Charter Sailing Destinations

British Virgin Islands

US Virgin Islands

Puerto Rico & Spanish Virgin islands

Cayman Islands

St Martin, St Barts, Anguilla, St Kitts & Nevis

Antigua & Barbuda

Martinique, St Lucia & The Grenadines

Latest Blog Posts

Sailing charter versus resort stay: comparing the costs

A sailing holiday frequently combines with a land-based resort stay. How many nights aboard charter boat and how many nights onshore, or foregoing one or the other due to cost, is often a discussion point. So we did an exercise on the price comparisons between boat and resort. The cost benefits of a sailing holiday are clear

Charter catamarans for modest sailing holiday budgets

Here we highlight some smaller catamarans finding favour with our charterers in the Mediterranean and elsewhere. Robert is our expert evaluator when it comes to helping you select the right boat for your sailing charter, and the following is his personal take on recent introductions to the charter boat market.

The popular Bali Catamaran in all its variations

The Bali catamaran, designed and built specifically with chartering in mind, has become so popular that it’s been hard to keep up with all the new models, hard to spot which one has just the right size and amenities to perfectly fit your group's sailing holiday charter needs. We can help you there.

The value of after-charter destination and boat reviews

At Sail Connections we offer a personal service based on long experience in the business and close attention to what's happening in the destinations we offer. We have also sailed a large number of those places, and can often speak from personal experience.  But we can't be everywhere.

Chartering in Turkiye: feedback we just have to share

Turkey is one of those charter destinations that doesn't fail to pleasantly surprise. We're always delighted when we receive such good reports as we did recently from a New Zealand client.

The Sail Connections Guarantee

One contact - every option - advice you can trust.

• Matching any competitive offer
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• Qualifying the operator as well as the boat
• Advising without bias based on 25+ years of experience
• We do more than just book yachts!

We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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Find Your Perfect Yacht

Caribbean yacht charters - one resource for every luxury charter yacht

The proven resource for crewed yacht charter in the caribbean.

From the moment you contact us, you will be helped by an experienced and knowledgeable specialist who will take the time to understand your unique needs and preferences for your caribbean vacation. They will be your dedicated specialist and our exceptional personal service will answer every question.

The largest choice of crewed Caribbean yachts?

Absolutely, with our relationships built over decades we truly do have access to EVERY crewed private charter yacht based in, or visiting, every part of the Caribbean.

Whatever the type of yacht for your Caribbean charter, your vacation budget, or the size of your party, our specialists will guide you in choosing the ideal yacht for your Caribbean charter. It's your vacation to explore the islands the very best way possible - on a Caribbean charter yacht.

Browse different types of Charter Yachts in the Caribbean

Motor Yachts

This category of Caribbean yachts include mega yachts, super yachts, and all sizes of power yachts. With the maximum space for guests, both inside and out, these types of yachts offer excellent vacations. You can choose from a fast, agile yacht, one that is high-end and luxurious, a yacht with a classic design, or one that is contemporary. This is one of the many choices you’ll have when you plan your vacation. See some yachts:-

Crewed Catamarans are very popular in the Caribbean , especially in the BVIs. Catamarans offer ample deck space that allows everyone to relax together during their charter, sharing the same views throughout the voyage. Caribbean catamarans can typically accommodate between 6 and 12 guests. See some yachts:-

Sailing Yachts

If you are looking for a winter getaway, there is no better place to charter a sailing yacht than the Caribbean! Feel the warm, tropical breeze on your face. Experience the exhilaration as the wind fills the sails and the yacht is suddenly moved along by just the wind. Savor the magnificent beauty of the Caribbean as you sail silently from one island to the next. Although typically offering smaller spaces for guests, sailboats deliver a truly unique caribbean charter vacations . See some yachts:-

Sample Charter Yachts in the Caribbean

ODYSSEA. The 59' sailing catamaran Odyssea is ready to take you and your guests on your next adventure. Throughout she offers relaxing areas to lounge and enjoy the voyage, while enjoying the company of others or absorbing the serenity of the sea. Her spacious cockpit area offers large dining table, sun pad across the back, and wet bar. See ODYSSEA:-

SOUTH. Get ready for adventure when you step on board the 180' mega yacht South. You and your guests will find plenty to do, as she offers plentiful spaces for lying out to enjoy the sun, enjoying a movie or game in the sky lounge, working out in the Techno gym with an amazing view, or enjoying the on deck Jacuzzi and watersports. See SOUTH:-

IMPULSE. The beautifully maintained motor yacht Impulse offers 87 feet of opulence at sea. She features three well-appointed cabins, a main salon, a bow with sunpads, flybridge with Jacuzzi, and a full complement of watersports including water skis, wakeboard, standup paddleboards, fishing gear, and the list goes on. See IMPULSE:-

LIQUID SKY. The 67' sailing catamaran Liquid Sky was launched in 2024 by Fountaine Pajot. With four cabins, she accommodates as many as eight guests, and offers a number of places for you to hang out and enjoy the journey, including on the bow soaking in the in deck Jacuzzi, up on the flybridge taking in the views, or on the aft deck with al fresco dining. See LIQUID SKY:-

MARIAH PRINCESS III. The 77' Lagoon built sailing cat Mariah Princess III was built in 2020. She offers two queen cabins and two king cabins, all en-suite. The master cabin has a private deck, the flybridge offers an on deck Jacuzzi, and she has a generous complement of watersports, including onboard SCUBA. See MARIAH PRINCESS III:-

TRUE STORY. The 67' sailing catamaran True Story is ready to give you and your guests a fun and exciting charter in the beautiful waters of the Caribbean. She offers a spacious main salon, large cockpit with al fresco dining and lounge, and flybridge with conversational area. You and your guests can also enjoy a long list of water toys throughout your journey. See TRUE STORY:-

The British Virgin Islands include Tortola, Jost Van Dyke, Virgin Gorda, and more. There’s no better way to experience the waters and beaches of the BVI's than on a private Caribbean charter with a full crew to pamper you. Of all the islands in the Caribbean, the Virgins are furthest north. This makes them very convenient due to the proximity to San Juan and due to their direct flights from the United States. Catamaran sailing vacations and crewed sailing charters are very popular in the islands, and their protected waters make them a favorite spot for guests that are taking their first private Caribbean yacht charter. To learn more about them:

The U.S. Virgin Islands consist mainly of the three large islands of St. Thomas, St. Croix, and St. John. With lovely bays, long beaches, lush nature preserves, fabulous diving spots, and excellent, onshore evening entertainment, many choose to vacation in the USVI’s. Caribbean charters often visit both the BVI’s and USVI’s during the same week, as they are close to one another and the waters are generally calmer than in other parts of the Caribbean. They in general are also home to the largest fleet of crewed, all-inclusive, luxury catamarans. To find out more about them:

The Leewards are situated in the middle of the Caribbean Island chain. The major airports are located on St. Maarten and Antigua. Due to the English, Dutch, and French influences everywhere you look, they exhibit the best example of cultural sophistication anywhere within the Caribbean. If you are looking to see where the rich and famous go on vacation, you will want to visit the island of St. Barts; for many this is a must stop for a Caribbean yacht charter. Many mega yachts are available for rental in St. Maarten, as it has become a popular mega yacht Caribbean base for the winter. To learn more about the Leewards:

The Grenadines are also called The Windward Islands. Oftentimes our guests will choose a sailing charter over a motor yacht when in the Grenadines, due to the more constant tropical breezes that occur. The islands are much less developed than the rest of the Caribbean, and the inhabitants live on their own time schedule, which enhances the feeling of getting away. The northern most island accessible by air is ST. Vincent, while the southern tip’s major airport is on Grenada. There are fewer Caribbean charter yachts based here; however, occasionally some charter yachts are happy to relocate in order to offer a vacation that happens a little off the beaten path. To find out more about the Grenadines:

What Type of Charter Yacht?

There are all types of Caribbean yacht charters available, including mega yachts, power yachts, catamarans, and sailboats. We have helped countless clients choose the right charter yacht, learning what features and amenities make a difference on caribbean charter yachts. Learn more about different types of Caribbean yachts.

Where Can You Go?

Typically you’ll choose between the Virgins, Leewards, and the Grenadines to charter your yacht. Beyond the region, it is your Caribbean to explore. It’s important for you to remember that there is no cruise ship itinerary to worry about! Your itinerary will be custom designed specifically for you, with you, and is flexible to changes during your charter. We have put together some samples for you to get an idea of what you might like to do while on vacation in the Caribbean. Interested in seeing a sample cruise itinerary ?

Find Your Perfect Yacht for a Caribbean yacht charter

To see the Caribbean yachts we have in our online database, please select a yacht type and your budget below. Please keep in mind that we do not have every available yacht online. There are many more yachts available for you to choose from when you contact one of our specialists.

For your personalized selection including yachts not online:- Email us now

Caribbean Charters - When To Go.

One of the lovely things about the Caribbean is that the temperatures remain consistent throughout the year; however, there are some other weather considerations that you will want to factor in when making your caribbean yachting vacation plans. Read More....

Vacations here are most popular between November and July.

If you are thinking of a megayacht, you will want to keep in mind that many of these private yachts which are Caribbean based in winter leave in the late spring and early summer months. They will return again in early winter; however, this does limit their availability. To charter a mega yacht, you will want to make sure that you do so well in advance.

Motor, sail, or catamaran yachts, on the other hand, often have selections available year round. Holidays like Christmas, New Year’s, and Easter do need to be planned for as early as possible as these are very popular charter times.

The availability for Caribbean charters can also be affected by the weather in other climates, for instance, when the severity of the weather is bad in the United States or Europe, especially between January and February, the charters are often booked. This is due to many clients looking for a break from the cold.

What Do Our Clients Say About The Caribbean?

Are you excited yet? You should be! Our clients have enjoyed fantastic Caribbean vacations. There is an endless number of places to visit in the Caribbean, from smaller islands to absolutely must be seen locations like St. Barts. Read some of our Caribbean charter reviews from clients who booked a Caribbean charter with us.

Ready to learn more about Caribbean charters?

We are specialists who will make your trip a reflection of our expertise! We know clients need to be confident in their charter vacation plans, so we encourage our clients to benefit from the knowledge base we’ve been building for years. You’ll speak to an authority on Caribbean charters without any obligation on your end.

Test our expertise with your questions!

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Utilize out firsthand knowledge about available charter yachts, crews and locations to book the best yacht and crew for your budget and travel style.

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Sail away to white sand beaches, consistent Caribbean trade winds, clear blue water, sheltered island bays great for cruising, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.

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These crewed catamaran charter specials are available for new reservations sailing from St Thomas or Tortola in the Virgin Islands, or elsewhere in the Caribbean. Contact us now for further information and a no-obligation quote.

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Caribbean Yacht Charter Vacations

A crewed Caribbean yacht charter offers you the freedom to explore this tropical paradise without limits and at your own pace.

With accommodation, a professional captain, a personal chef, all meals, cocktails, wine, beer, snacks, fuel, equipment, and water toys included, few other vacations offer such an extraordinary experience and value.

Itineraries are completely flexible within your cruising area. Sail the diverse US and British Virgin Islands, the undeveloped and resort islands of the Caribbean Grenadines, or charter a luxury power yacht to cruise St. Martin, St. Barts, and Antigua in the Caribbean Leeward Islands.

Sailing Direction's charter brokers help you book a private crewed yacht in the Caribbean for any group size and budget. Whether you're looking for a family sailing vacation, a couple's adventure holiday, a BVI yacht charter, or a honeymoon or anniversary celebration - we've got you covered for an unforgettable crewed yacht charter experience.

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794  Crewed Luxury Yachts for Charter in the Caribbean

• Caribbean Yacht Charter

A Caribbean yachting vacation incorporates vast expanses of crystalline waters and endless clusters of idyllic paradisical islands, making for a picture-perfect family getaway. With its beautiful climate and spectacular coastlines that comprise iconic superyacht hotspots like the  Virgin Islands ,  St Barts  and  Antigua , a yacht rental in the Caribbean has an alluringly evergreen appeal.

Caribbean Yacht Booking Guide:

Caribbean Yacht Charters: At a Glance

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The Caribbean Sea comprises more than 7,000 islands, islets, reefs and cays, and is divided into three island arcs: that of the Greater Antilles in the north, the Lesser Antilles in the south, and the Leeward Antilles to the east.

• Ideal winter destination Boasting all-year-round pleasant weather, its powdery sand beaches and alluringly clear waters make it an especially popular choice for winter yacht charters.
• Easy-to-reach The Caribbean is well-connected to the US, with a high number of international airports flying directly into the region.
• Secluded anchorages With more than 7,000 islands and only a small percentage being inhabited, the world is your oyster when it comes to finding serenely beautiful anchorages.
• Snorkeling and diving paradise The Caribbean is home to some of the world's most impressive snorkeling and diving sites, meaning plenty of exciting underwater adventures where your eyes will be wide with wonder.
• Excellent superyacht marinas The Caribbean has numerous well-provisioned superyacht marinas to take your pick from, many of which have fantastic dining and shopping opportunities.

While the Bahamas is technically part of the Caribbean region, it is an island nation in its own right, forming part of the Lucayan Archipelago in the Atlantic. That said, the Caribbean is a vast area occupied by thousands of islands, coral reefs and islets, of which the Bahamas forms a part, along with strong political and cultural ties that have created a natural bond with its Caribbean neighbour. 

Practically speaking, however, if you are interested in cruising  the Bahamas  in conjunction with your Caribbean yacht charter, it is highly unlikely you'll be able to manage the distance during a typical 7-day charter, especially for itineraries that incorporate East Caribbean destinations such as Antigua and Saint Martin. You will need to decide which destination you prefer to spend your time in, or extend your charter vacation to incorporate both. 

To find out more about chartering in the region, check out our in-depth Bahamas destination guide for more information.

The most popular destinations for renting a yacht in the Caribbean are those located in the Lesser Antilles region, primarily the island groups of the Leeward Islands.  and the  Windward Islands .

For Leeward Island yacht rentals , Antigua, the Virgin Islands, St Martin, St Barts and St Kitts and Nevis garner the most attention, thanks to not only their splendid tropical landscapes but also their extremely well-provisioned superyacht marinas, fine dining options, impossibly hip bars and medley of designer boutiques bound to keep guests entertained from dawn till dusk.

Scattered like pearls along the aquamarine seas, you'll find sun-drenched Martinique, gorgeous Grenada and the ultra-secluded St Vincent and the Grenadines  are the top picks for slow-paced  Windward Island yacht charters .

Although not as popular, the islands that form the Greater Antilles , such as Jamaica, Cuba and Puerto Rico , are just as beautiful and offer an array of spectacular destinations to explore and discover on a luxury yacht charter.

Looking for the best superyacht hotspots in the Caribbean? These are the spellbinding locations guests find most enticing. If you are interested in any of these cruising grounds, we strongly advise booking as far in advance as possible.

• Antigua: the jet-set adore its unbelievable scenery, intriguing historical landmarks, lavish shopping options and a cluster of ivory-white sands coupled with gin-clear waters.
• St Martin/Sint Maarten : French and Dutch sides of the island combine to bring a fascinating fusion of influences, replete with outstanding diving spots and awe-inspiring topography. 
• St Lucia : considered the tropical jewel of the Windward Islands, it's virtually unspoiled. Bordered by lush rainforest and dark volcanic sands, it makes for a truly unique anchorage spot. 
• Grenada : known as the Isle of Spice thanks to being one of the world's largest exporters of mace and nutmeg, its capital St George is regularly called the Caribbean's most picture-perfect town. 
• St Barts : Well-known for its moniker "St Moritz of the Caribbean" due to its unique Swedish-French colonial heritage, this iconic tiny island is synonymous with glamour, movie stars and designer shopping. 
• St Croix, US Virgin Islands : The largest of the USVIs boasts a National Park, breath-taking scenic beauty and some of the best dive spots in the Caribbean.
• Puerto Rico : Affectionately known locally as the ‘island of enchantment’, Puerto Rico is a profusion of vibrant Latin culture entwined with the laid back rhythm of the Caribbean, with pristine beaches, excellent diving spots and exquisite local dishes.

A yacht rental vacation in the Caribbean delights guests with its truly endless number of things to see and do. Here are our top picks:

Don't Miss:

• Eden Rock St. Barts : one of the most in-demand hotels in the Caribbean, with a seven-star bar and spa.
• Hermitage Bay, Antigua : kick back and relax on this tropical beach that delivers on sensational views.
• Bagatelle, St. Barts : overlooking the glittering Gustavia harbor, this sophisticated bar and restaurant is a hugely popular superyacht spot, showcasing the finest of French-Caribbean cuisine.
• Basil's Bar, Mustique : legendary bar and restaurant designed by Philippe Starck, frequented by royals, supermodels and rockstars for decades.
• The Cotton House, Mustique : a wellness center unsurpassed in beauty.
• Watermelon Cay, St John, US Virgin Island s: dreamy islet surrounded by coral reefs and a veritable snorkeling wonderland
• Rhone Marine Park, British Virgin Islands : the wreck of the RMS Rhone is the BVIs' most popular dive site, and arguably one of the best in the Caribbean.
• Trunk Bay, St John, US Virgin Islands : all dazzling white sand lapped by the bluer-than-blue ocean, this island paradise ranks consistently among the world’s top 10 beaches.
• Jardines del Rey archipelago, Cuba : known locally as the ‘King’s Gardens’, this collection of islands is a registered UNESCO Biosphere Reserve and an island-hopper's paradise, offering myriad secluded beaches and sensational sunsets.

For anyone looking to get a dose of serious sunshine during the Northern Hemisphere winter, a yacht charter in the Caribbean is a seriously enticing prospect, with St Barts being the clear favorite for Christmas and New Year's Eve, thanks to the showstopping celebrations that take place in Gustavia Harbour.

For avid island hoppers, the Windward islands offer an enchanting itinerary full of sun-kissed isles and laid back charm juxtaposed with chic resorts and heavenly French-based cuisine, not to mention unrivalled vistas and sultry sunsets accompanied by warm rum-laced winds. 

Across all Caribbean destinations, keen divers and snorkelers will be in for a subaquatic treat, and you'll find a wide range of designer boutiques and ultra-high-end resorts peppered across the isles wherever you go.

The Caribbean is a mesmerizing melting pot of cultures and influences, rooted in its rich heritage and undeniably shaped by its history of colonization and waves of immigration. Each island group is highly diverse in terms of its language, music, customs, architecture and cuisine, but it's mainly English, Dutch, French or Spanish colonial influences that are keenly felt. While the mix of languages spoken will differ between island groups, English is widely spoken.

Caribbean cuisine sees influences from Africa, Europe, Latin America and Spain, Meat, seafood, coconut, potatoes, beans and tomatoes tend to feature heavily in local dishes.

Locals are friendly and regularly celebrate their culture, with music, food and wildly colorful festivals held throughout the year.

A luxury yacht rental vacation in the Caribbean is, without doubt, the most sublime way to experience this region, giving you exclusive access to heavenly anchorages that are otherwise impossible to reach or are far from the typical tourist trail.

Guests have boundless fleet options when it comes to a crewed Caribbean charter. If you don't know whether to go for a motor yacht, sailing yacht or catamaran to cruise Caribbean waters, we've laid out the main points worth considering.

Motor Yacht Charters in the Caribbean

A  luxury motor yacht charter  in the Caribbean is a seven-star way of uncovering the epic beauty of the Caribbean in total privacy. 

For regions with minimal water depth the ideal choice is a motor yacht with low draft, perfect for accessing shallow lagoons and secluded bays.

For those who have their heart set on a superyacht without a shallow draft, dropping anchor further out into deeper waters and then getting a tender ride ashore, so you can get up close and personal to exquisite island reefs and blue lagoons, is the preferred option.

Sailing Yacht Charters in the Caribbean

Chartering a sailing yacht in the Caribbean is ideal for guests looking for a slower pace to fully lap up the Caribbean rays with more outdoor deck space, and add a little old-school charm to their cruising adventure.

Even better, the majority of sailing charter yachts come equipped with a retractable keel, meaning reaching turquoise shallows is a breeze. But, if you are keen to charter a larger sailing yacht, keep in mind that some may still find their draft too deep for some areas, even with the keel up. 

Catamaran Charters in the Caribbean

Luxury catamaran charters are a firm guest favourite for those embarking on Caribbean vacation, especially in the Bahamas and the Virgin Islands. Thanks to their shallow draft, catamarans give you the ability to get close to cays and islets guests can savor the thrilling feeling of being able to jump off-board at almost any point. 

The charter cost of a motor yacht, sailing yacht or luxury catamaran rental in the Caribbean will vary according to the vessel's size, age, type, number of crew, as well as the location and duration of the vacation as well as the season it takes place. 

With so many options available, there’s something to suit every type of budget. For convenience we have listed the average prices for motor yacht and sailing yacht charters in the Caribbean below;

• For motor yacht rentals in the Caribbean, prices can range from $39,167 to $1.4m per week, plus expenses
• For luxury sailing yacht rentals in the Caribbean, prices can go from $29,855 to $276,495 weekly, plus expenses

The best time for luxury yacht charters in the Caribbean is between November and March, when guests can expect clement weather and vividly blue cloudless skies.

Another aspect to keep in mind is that this is also the time when you will have the largest selection of yachts to choose from, as most charter yachts descend on the Caribbean around November after the Mediterranean season has ended and any yacht maintenance has been carried out, before returning back to the Mediterranean in March/April.

The most popular starting point for a Caribbean yacht rental is usually in either Saint Martin/Sint Maarten or  Antigua,  both of which have international airports.

It is certainly possible to begin your charter in other Caribbean destinations, providing this has been agreed with the Owner and charter broker .

Where to End a Caribbean Yacht Charter

For most private Caribbean yacht charters, there isn't one definitive place where to disembark given the vastness of the region. However, what is likely is that you will finish your yacht rental vacation in the same location that you started. For example, the majority of  British Virgin Island yacht charters will begin and end in St Thomas, while for Antigua yacht charters , it'll be the iconic English Harbour.

sample itineraries

The Caribbean offers some of the most spellbinding berthing spots in the world. These tropical, barefoot hotspots are of the finest calibre, surrounded by jaw-dropping scenery, and often feature award-winning restaurants, hip boutiques, beach bars and more.

But which marinas are the best? Below are some charter favorites:

• Falmouth Harbour, Antigua: impressive marina facilities and scenery, catering to yachts up to 100m.
• Marina Fort Louis, Saint Martin: offers 150 berths for yachts up to 79m.
• Crown Bay in St Thomas (USVI): full-serviced marina with 99 slips, including 16 berths for superyachts up to 60m
• Port Louis Marina, Grenada: idyllically located, with 227 moorings for yachts up to 91m.
• Port de Gustavia, Saint Barts: widely regarded as one of the most beautiful natural harbours in the world, accommodating up to 152 yachts up to 152m.
• Puerto Del Rey, Puerto Rico : conveniently located as a jumping off point for yacht charters incorporating the Virgin Islands and Lesser Antilles, this marina has plentiful wet slips, including capacity for yachts up to 200ft (60m) LOA.

We strongly advise booking through a qualified  yacht charter broker at least three months in advance for all Caribbean yacht charters. By doing so, you will increase the likelihood of securing your preferred dates and you will have a greater selection of yachts on offer to choose from.

This also ensures your yacht broker has enough time to craft a carefully curated itinerary and secure an overnight berth in the most popular Caribbean marinas.

related articles

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Explore the Caribbean

Guide to Bahamas

Guide to Virgin Islands

Guide to Leeward Islands

Guide to Windward Islands

Guide to Greater Antilles

Guide to Turks & Caicos Islands

Guide to Barbados

Guide to Trinidad & Tobago

The caribbean yacht charter itineraries.

Make every moment count during your superyacht vacation with our carefully curated yacht charter itineraries, tailored so you can experience the very best of the paradisiacal islands of the Caribbean and ensure your yacht charter is a truly memorable one. Designed by yachting experts, we've cultivated itineraries that will satisfy a range of requirements.

For yacht charter guests seeking a little glitz and glamour on their vacation, a 7-day charter around the Leeward Islands is a must, comprising Caribbean gems such as Saint Barthelemy, renowned for its A-list celebrity culture and designer shopping, as well as the perennial favourite Antigua. For sheer unadulterated bliss, incorporate the Virgin Islands on a 14-day yacht charter, promising idyllic stretches of pristine sands lapped by waters in every shade of blue.

Discover the Caribbean

Winter Getaways, Tropical Paradise Islands, Snorkeling & Scuba Diving, Crystal Clear Waters, Beautiful Secluded Anchorages, Well-Provisioned Superyacht Marinas

When to Go:

December - March

International Airports:

• Princess Juliana Airport (St. Maarten)
• V.C. Bird Airport (St. John's, Antigua)
• Luis Muñoz Marín Airport (Carolina, Puerto Rico)
• Grantley Adams Airport (Bridgetown, Barbados)
• Lynden Pindling Airport (Nassau, The Bahamas)

Luxury Yachts for Charter in the Caribbean 2024 & 2025

Crewed charter yachts in the caribbean.

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92m   Neorion

from $1,100,000 p/week ♦︎

115m Lurssen

115m   2021

from $2,895,000 p/w eek ♦︎

Black Pearl 14

105m Oceanco

105m   2018

Christina O 34

99m Canadian Vickers

99m   1943/2020

from $778,000 p/w eek ♦︎

Carinthia VII 12

97m Lurssen

97m   2002/2023

from $1,559,000 p/w eek ♦︎

97m Feadship

97m   2017/2022

from $1,778,000 p/w eek ♦︎

CC-Summer 12

95m Lurssen

from $1,732,000 p/w eek ♦︎

from $1,334,000 p/w eek ♦︎

93m Feadship

from $1,556,000 p/w eek ♦︎

Aquarius 12

92m Feadship

from $1,500,000 p/w eek

Queen Miri 36

92m Neorion

92m   2004/2023

from $1,100,000 p/w eek ♦︎

Lady Lara 12

91m Lurssen

91m   2015/2023

from $1,400,000 p/w eek

90m Corsair Yachts

90m   2007/2021

from $497,000 p/w eek

90m Oceanco

90m   2018/2024

89m Oceanco

from $1,100,000 p/w eek

89m   2015/2023

Maltese Falcon 12

88m Perini Navi

88m   2006/2023

from $490,000 p/w eek

86m Scheepswerf Gebr. van der Werf

86m   1998/2024

from $531,000 p/w eek ♦︎

Man of Steel 12

86m Oceanco

86m   2010/2023

from $1,000,000 p/w eek

86m Abeking & Rasmussen

86m   2009/2024

from $953,000 p/w eek ♦︎

O'Ptasia 12

85m Golden Yachts

85m   2018/2024

from $1,000,000 p/w eek ♦︎

Victorious 12

85m Ak Yachts

from $889,000 p/w eek ♦︎

Le Ponant 32

84m   1990/2022

from $506,000 p/w eek ♦︎

Savannah 12

84m Feadship

84m   2015/2020

from $1,111,000 p/w eek ♦︎

Elements 12

80m Yachtley

Excellence 12

80m Abeking & Rasmussen

from $1,150,000 p/w eek

Amaryllis 12

78m Abeking & Rasmussen

78m   2011/2022

from $770,000 p/w eek

78m Golden Yachts

78m   2023/2024

from $811,000 p/w eek ♦︎

from $480,000 p/w eek

Huntress 12

76m Lurssen

76m   2009/2022

from $725,000 p/w eek

75m Admiral Yachts

75m Feadship

from $900,000 p/w eek *

75m Abeking & Rasmussen

from $880,000 p/w eek

Starburst IV 12

from $1,011,000 p/w eek ♦︎

74m Nobiskrug

74m   2008/2013

from $561,000 p/w eek ♦︎

73m Delta Marine

73m   2006/2015

from $525,000 p/w eek

Nautilus 12

73m Picchiotti

from $834,000 p/w eek ♦︎

73m Lurssen

73m   2006/2020

from $615,000 p/w eek

Quantum of Solace 12

73m Turquoise Yachts

73m   2012/2022

from $574,000 p/w eek

Game Changer 17

72m Damen Yachting

72m   2017/2020

from $450,000 p/w eek

72m   2010/2023

from $600,000 p/w eek

72m Dunya Yachts

72m   2013/2020

from $660,000 p/w eek

Talisman C 12

71m Turquoise Yachts

71m   2011/2020

from $567,000 p/w eek

70m Feadship

from $650,000 p/w eek

Sherakhan 26

70m Vuijk Scheepswerven

70m   2005/2022

from $594,000 p/w eek ♦︎

69m Feadship

69m   2012/2019

from $610,000 p/w eek ♦︎

Sycara V 12

68m Nobiskrug

68m   2010/2017

Wayfinder 12

68m Astilleros Armon

from $375,000 p/w eek

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68m   2010/2020

from $540,000 p/w eek

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67m   2011/2019

from $361,000 p/w eek ♦︎

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from $680,000 p/w eek

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67m   2007/2008

from $120,000 p/w eek

66m   2014/2023

66m Rossinavi

from $637,000 p/w eek *

Invictus 12

66m Delta Marine

66m   2013/2020

from $650,000 p/w eek *

65m Benetti

Ventum Maris 12

66m   2011/2021

from $530,000 p/w eek

Eternity 17 7 12

65m Codecasa

65m   2010/2022

from $390,000 p/w eek

Illusion 12

65m   2013/2019

from $462,000 p/w eek

Resilience 12

Silver Angel 12

64m Benetti

64m   2009/2015

from $425,000 p/w eek

64m   2016/2021

from $475,000 p/w eek

63m Halter Marine

63m   1978/2022

from $350,000 p/w eek

Lady Britt 12

63m Feadship

from $465,000 p/w eek *

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Caribbean Yacht Charter Q&A

The best time to visit the Caribbean is generally December to April, when it's a little cooler and less humid. But the best month to visit can differ depending on the island, budget and interests you have. For example, some yacht charter guests may decide to visit May to June and late November, when weather is still fantastic but there are fewer crowds.

We advise booking your Caribbean yacht rental at least three months in advance to ensure you get the yacht you desire. The longer you leave it, the fewer choices you will have to rent in the Caribbean.

For your Caribbean superyacht charter, you will need to provide a completed charter agreement and 50% of the charter fee as a deposit. This is payable once the contract has been signed.

When booking a Caribbean yacht rental, do keep in mind the costs that aren't included in the base rate, namely VAT and the APA (Advance Provisioning Allowance). The APA is usually paid in advance of the charter and is commonly set at 30% of the charter fee. This allowance covers expenses such as fuel, berthing, food and drinks, as well as any special requests. 

Please consult your yacht charter broker for any other costs you may need to factor in for your yacht charter in the Caribbean.

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Find Caribbean Crewed Yachts for the Vacation of a Lifetime

The Caribbean is one of the most popular destinations for yacht charters in the world, featuring crystal-blue waters, white-sand beaches, and more than 5,000 islands and cays to explore. With so many islands to choose from, your Caribbean yacht charter itinerary can be tailored to your preferences, giving you the perfect opportunity to island-hop and explore everything the tropical islands have to offer while comfortably kicking back inside luxurious accommodations on the water.

On your private yacht charter , you will be able to explore lively harbors, secluded beaches, tropical rainforests, world-class dive sites, and much more. The possibilities are endless!

Caribbean Yacht Charter Highlights

• More than 5,000 islands and cays to explore
• A great winter destination
• Crystal-clear, sparkling blue waters
• Long stretches of white-sand beaches
• Luxury hotels, five-star restaurants, and spas
• Islands with their own unique cultures and cuisines
• A large selection of crewed yachts for charter

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Caribbean Yachting Season

The Caribbean high season for yacht charters runs from mid-December to early May, with Christmas and New Year’s the most popular and busiest times of the year. But due to the islands’ locations near the equator, temperatures remain ideal throughout the year, making off-season charters just as enjoyable.

Keep in mind, however, that there is an increased chance for storms and hurricanes during the summer season, mainly from mid-August to mid-November. Most charter yachts leave the area during that time.

Caribbean Crewed Motor Yacht Charters

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Area Guide: Caribbean Charter Destinations

Are you ready to explore all that the Caribbean has to offer? There are three main island areas in the Caribbean, all fantastic destinations for Caribbean charter yacht vacations.

The Grenadines

The Grenadines are untouched by mass tourism and industry, and they are the perfect charter destination if you are looking for solitude and you enjoy exploring remote areas. A great combination of lush rain forests and sandy beaches awaits!

This is a great summer charter destination because the islands aren’t usually affected by hurricanes.

The Leeward Islands

Leeward Islands yacht rentals offer the perfect combination of luxury and solitude. You can visit the glitzy islands of St. Maarten and St. Barts one day and get lost in the remoteness and tranquility of Anguilla the next day.

These islands are rich in history and offer great restaurants, upscale resorts, and trendy harbors.

The Virgin Islands

The Virgin Islands are the perfect location for first-time charterers and families because of their calm waters, protected natural anchorages, and short distances between the islands.

The BVI are a great destination for a catamaran or sailing yacht charter. Caribbean locations here have constant yet mild trade winds year round, and the area offers fantastic diving and snorkeling.

Where Can I Charter a Yacht?

When you choose Worldwide Boat as your Caribbean yacht charter broker, we can help you charter a luxury boat anywhere in the Caribbean or anywhere else you’d like to go, from the Mediterranean to Alaska to the Galapagos Islands.

How Do I Book a Private Yacht?

The best Caribbean yacht charters can be booked in just a few easy steps:

• Choose our experienced yacht charter specialists to assist you through the process of booking a yacht.
• Search by destination or by boat, or use our advanced search tool to filter your options by the number of guests, yacht type, destination, and/or your budget.
• Pick the option that best fits your needs and your dream vacation.
• Reserve your yacht by signing a contract with the yacht owner.
• Enjoy your vacation!

How Much Does it Cost to Charter a Yacht in the Caribbean?

Weekly rates for Caribbean boat charters are dependent on a number of factors, including the type of yacht, the season, and your destination. Motor yachts, for example, typically range from $15,000 (yachts up to 80 feet) to $150,000 or more (yachts over 150 feet) per week.

During the Caribbean high season (Christmas, New Year’s, and January/February), yacht charter Caribbean prices tend to increase slightly. Areas with large charter fleets, like St. Martin, tend to have more competitive pricing than areas with smaller fleets.

How Much Does it Cost to Charter a Catamaran in the Caribbean?

Most catamarans offer all-inclusive rates, which start at $10,000 for catamarans under 50 feet and run up to $50,000 or more for catamarans of 80 feet or more. The Caribbean is an ideal destination for a catamaran charter, and across the region, you’ll find a variety of sailing and power cats available for charter.

Ultimately, the cost of a catamaran charter is dependent on the time you visit, where you go, local taxes, and the number of ports you visit. A luxury yacht charter in the Caribbean’s high season (New Year’s or Christmas) will cost significantly more than a catamaran charter in summer.

Can I Rent a Yacht for a Day?

Rates for yacht rentals are usually weekly, but when you talk to a Caribbean yacht charter broker at Worldwide Boat, we can look at your budget, plans, and interests to help you get the best experience possible.

Caribbean Yachting Hotspots

Caribbean sailing charters give you access to white-sand beaches and laid-back island vibes, but they can also offer action-packed itineraries. From island-hopping and hiking to snorkeling and cliff-jumping, adventure awaits on a Caribbean yacht charter!

Some of the region’s must-see destinations include:

• St. Martin : Known for its upscale eateries and amazing cuisine, as well as high-end spas, shopping and casinos, St. Martin is the yachting capital of the Caribbean. This island is part French and part Dutch, and it’s close to islands like St. Barts and Anguilla, making it a favorite jumping-off point for island-hopping adventures.
• St. Barts : St. Barts (sometimes called St. Barths) beckons A-listers to its posh beach clubs, fashionable shops, and five-star eateries. Visitors will find a collection of truly spectacular powdery beaches, Michelin-starred restaurants, and excellent shoreside amenities, all within cruising distance of St. Martin.
• Antigua : Antigua epitomizes the relaxation and bliss of the Caribbean. Known for its 365 beaches (one for every day of the year), the tiny island is a sailor’s dream, offering warm waters, steady winds, safe anchorages, and a lively regatta calendar.
• Grenada : Grenada is revered for its beautiful beaches, abundant marine wildlife, and vibrant cuisine (spiced with local nutmeg, mace, and allspice). Spend a day relaxing on Grand Anse Beach, which is consistently ranked one of the best in the world. Island-hop to neighboring isles like Petite Martinique, or spend a day snorkeling one of Grenada’s famous reefs.
• Anguilla : Anguilla is one of the most tranquil Leeward islands. Escape to Dream Bay or one of the numerous nearby coral cays for some supreme R&R. A diving and snorkeling mecca, Anguilla is home to some of the Caribbean’s best shipwreck dives. Plus, the island boasts a calendar of must-see festivals and events, including a jazz festival in November and Carnival in August.

Why Charter a Yacht in the Caribbean?

The best Caribbean yacht charters offer a bit of everything: Relaxation, sun-soaked beaches, delicious culinary treats, refreshing rum-infused cocktails, and calm waters for cruising. Here are some highlights:

The Inescapable Beauty of White-Sand Beaches

Caribbean beaches have almost a mythical quality to them. It’s no wonder explorers were once willing to board wooden ships and travel thousands of miles just to see them in person.

Every island offers a selection of untouched and charming beaches for you to explore. From one-of-a-kind places like “Pig Beach” in the Bahamas to the cosmopolitan Great Bay Beach in Philipsburg, St. Martin, the beaches across the Caribbean offer legendary sights and attractions.

Colorful Celebrations and Friendly Faces

The Caribbean is known for its parades, bars, nightclubs, and parties, not to mention world-famous cocktails. When you want to step off of your luxury yacht charter, Caribbean shores and islands offer a world of fun to immerse yourself in.

A few must-see events include the St. Barth’s Bucket (if you’re into superyacht racing), the annual Carnival celebration, and the St. Lucia Jazz & Arts Festival .

Amazing Wildlife and Adventure

If snorkeling in vibrant and colorful coral reefs, diving into underwater museums, or parasailing over clear waters are some of the items on your bucket list, you can certainly get it all done during your visit to the Caribbean.

You’ll find a variety of unique adventures, from the underwater sculpture park of the Grenadines to the natural seaside baths in Virgin Gorda and hiking the Pitons in St. Lucia. The Caribbean gives you to plenty of chances to get outside and enjoy yourself.

Nonstop Relaxation

Because the area is so close to the equator, the Caribbean offers warm weather to lounge in all year round. Feel pampered aboard a luxury crewed rental yacht, and then feel calm while sinking your toes into soft, powdery white sand. Enjoy the spas, rum cocktails, and quiet, isolated beaches: Charter guests can experience supreme relaxation in the Caribbean.

Book Your Caribbean Charter With Worldwide Boat

Discover the beauty of the Caribbean with a luxury crewed yacht charter. Contact a broker with Worldwide Boat today to learn more about available yachts and itineraries for the Caribbean.

Last edited by Katja Kukovic

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VOYAGE Charters invites you on a private, luxury, Caribbean vacation. Our yacht charters include Bareboat, Yacht & Captain, and All-Inclusive Crewed. Let our friendly staff, captains, chefs, and concierge services help you experience the perfect sailing vacation in the British Virgin Islands.

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• Caribbean Yacht Charter

Perhaps the best tropical yacht charter spot worldwide, there are over 700 islands to choose from in the Caribbean. However, Caribbean yacht charters can be split into two main area: the Greater Antilles and the Lesser Antilles. The Greater Antilles is home to countries like the Dominican Republic, Jamaica and Cuba while the Lesser Antilles can be subdivided into the Windward and Leeward Islands. The Leeward islands include St Kitts and Nevis, the British Virgin Islands, Anguilla along with Antigua and Barbuda. The Windward Islands comprise the Grenadines, Grenada, Barbados, Dominica, St Vincent and St Lucia.

ALFA NERO | From EUR€ 812,000/wk

Maltese falcon | from eur€ 480,000/wk, seven sins | from eur€ 270,000/wk, g2 | from us$ 85,000/wk.

Sailing Yachts Under 100' - Sailing Yachts Over 100' - Motor Yachts Under 100' - Motor Yachts Over 100' - Catamarans Over 50'

The stunning and diverse Caribbean beckons travelers back year after year. With its beautiful climate, fantastic coral reefs, palm trees and exotic tropical islands, there are lots of reasons to make this your next sailing destination. Don’t forget the rum cocktails either! As the second largest yachting area, only after the Mediterranean, there are many luxury yachts available for your Caribbean yacht charter and you can view some of the yachts below or here .

Reviews of Caribbean Charter Vacations | Caribbean Holiday Fact File | Top Caribbean Spots | Sample Itinerary | Charter Yachts Available

The Bahamas and Turks and Caicos are not really in the Caribbean although are known as superyacht destinations in the Caribbean. Wherever you decide to charter a luxury superyacht in the Caribbean you will enjoy a totally relaxing vacation and beautiful scenery.

How Much Does it Cost To Charter in The Caribbean?

Caribbean yacht charter prices vary according to the size, style and age of the yacht you rent. Our luxury superyacht charters rent from 30,000 USD to over 1,000,000 per week, plus expenses, in the form of an advanced provisioning allowance (APA). Conversely, smaller 'all inclusive' type vacations cost between USD 15,000 to 50,000 per week. View the list of yachts and prices here .

Experience the luxury of Crewed Private Yachts in the Caribbean

A traditional hot spot for crewed charters, the Caribbean is considered “the king of yachting vacations”, so please contact us here to go on your private charter. Whether you agree with this or not, you like most people will have heard of the Caribbean as a great yacht charter destination. This is because this location covers a huge area and offer fantastic diversity. It is beautiful and warm, has amazing beaches, interesting cultures and perhaps most importantly, the Caribbean has a huge selection of crewed yachts, luxury yachts and superyachts which you can rent and experience a truly magnificent vacation around the various Island groups. The Caribbean is a natural wonderland onshore, but probably most importantly, it has an ocean laden with treasures, from tiny beach ridden coral atolls to substantial mountainous islands exuding rich and colorful cultures. An area which is famous for its beautiful waterways and islands, there is no better way to experience the Caribbean than on a crewed luxury yacht vacation.

Some of the Recommended Caribbean Yacht Spots:

Popular places to visit on a yacht include Antigua , St Barts , Anguilla , St Martin , The British Virgin Islands , The US Virgin Islands , the Grenadines and many more – see more below.

More than ever crewed luxury yachts are beginning to explore more exotic and remote Caribbean Islands, so ask your charter broker or captain for more information on some of these more remote treasures. Due to the scale and diversity of the different areas of the Caribbean we have covered the major charter locations individually. Please note that if there is a charter boat cruising area, not covered here that you are interested in, please contact us and we will provide you with that information personally in the form of a yacht charter itinerary.

As one of the most popular locations in the world, second only to the Mediterranean in popularity, the types of boats available for rental in the Caribbean include all the main types such as motor, sailing, skippered, crewed yachts, catamarans, power boats, sailboat, luxury yachts as well as the ever growing superyacht and mega yachts. Both beginner and experts alike are drawn to the Caribbean for its warm winds, protected waterways and beautiful anchorages. The Caribbean is a special place that has beautiful tropical islands that lie snug within a tropical island necklace as laid out on a large blue sea.

The Caribbean is also steeped in a fertile history of sailing adventure. Ever since the days of galleons and pirates the Caribbean has been host to some of the most satisfying sailing anywhere in the world. On your Caribbean yachting vacation you can find, an incredible amount of choice and variety and all in a relatively small area - thriving bars and Caribbean nightlife; first rate cuisine; spectacular white powder beaches; lush tropical rain forest; cloud-fringed mountain peaks; exotic bird life; amazing diving and snorkeling and a serene blend of European sophistication and warm Caribbean hospitality. The problem is, with so many superb Caribbean yachting locations and charter boats to choose form, where do you start when planning a holiday? With CharterWorld of course…

The Time of Year to Charter a Yacht in the Caribbean:

The main Caribbean sailing season runs from November through to July. The Caribbean primary high season is from mid-December to March, when the winter escapees from North America and Europe arrive in their greatest numbers. The hurricane season is from late July to early October, although hurricanes are in general rare in the southern Caribbean. Unfortunately, they can be prevalent around Cuba, Bahamas and the east coast of the U.S. every few years. This is the least expensive time for chartering in the Caribbean and there are some really good deals are available. However, as well as running the risk of storms, this time of year also tends to be associated with lighter (or non-existent) winds.

As with many boating locations the Caribbean shoulder season, in this case from April to July, is also a great time to charter a boat as there are less shore based visitors, some lovely settled sunny weather, and warm yet steady breeze. The Caribbean is made up of many different multi-nation (and multi-cultural) volcanic islands. There are amazing sailing grounds stretching from Cuba and Jamaica in the west, through the Dominican Republic, Puerto Rico, The Virgin Islands, The Leeward Islands and the Windward Islands, finishing with Trinidad and Tobago off the coast of Venezuela.

Caribbean Yachting Hot Spots:

Here is a brief list of some of the Caribbean hot spots to consider experiencing when you rent a luxury crewed charter yacht. This is by no means an extensive list and there is more information on things to see and do in the Caribbean under each Caribbean private yacht location. Also, when you hire a yacht with us we will supply you with a customised hand written itinerary suggestion so that you and your crew have a few ideas to choose from on your charter.

General Places/Events Worthy of Experiencing:

- Gustavia Harbour in St Barts - shopping, nightlife, restaurants and European quintessence - Nelson in Dockyards in Antigua - history and beauty in a harbour - Sunset in St Lucia - St Kitts for the beauty, history and magnificent views from Brimstone Hill Fortress - Anegada for its deserted beaches, fringed reefs and the unique flora and fauna of the salt ponds, home to the pink flamingo - The BVIs for the beautiful beaches and anchorages - Guadeloupe for its diversity - one side offers cosmopolitan flair, bordered by beaches and coral reefs and the other has open lands with the fertile, volcanic peaks , rain forest and waterfalls.

How to get to the Caribbean

There are direct flights from the UK and the US to Barbados, Jamaica, St Lucia and Antigua. Some Caribbean islands require a connecting flight as they have small airports which cannot handle large aeroplanes. Across the Caribbean, many islands have private jet facilities with fantastic runways.

What is the currency in the Caribbean?

Various currencies are used in the Caribbean. For instance, in Anguilla, Dominica, Grenada, St Kitts and Nevis, St Lucia, St Vincent, the Grenadines and Antigua, the East Caribbean dollar is the currency. Jamaica, Barbados, the Cayman Islands and the Bahamas have their very own currency. US dollars are accepted on most of the islands however the ATMs tend to have only the local currency.

Language spoken

There are four main languages spoken in the Caribbean, French, Spanish, Dutch and English. English is the first or second language and is mostly used when tourists visit. The official language of Haiti is Haitian Creole while Papiamento is used in Curacao, Bonaire and Aruba. Different creoles and local patois are also spoken on the various islands.

Time Zone in the Caribbean

Two time zones are used in the Caribbean. GMT -5 and GMT -4. Daylight saving time is implemented in many countries including Bermuda, Cuba, Haiti, the Bahamas including the Turks and Caicos Islands.

Visas and customs immigration

British and American tourists do not need visas if they are staying in the Caribbean for less than 90 days. It’s advisable to check the exact requirements for the countries you intend visiting. American tourists are still not allowed to visit Cuba although this may change in the future.

What to consider medical/health wise when chartering a superyacht in the Caribbean

There aren’t any extra medical issues for travelers in the Caribbean but check with your travel agent for any current warnings. The most common are complications form insect bites, jelly fish stings, cuts from coral and heart-related illnesses.

Short List of Caribbean Sailing Yacht Events:

- Antigua Sailing Week – held during the last week of April each year, yachts from all over the world arrive in English and Falmouth Harbours for an action packed week on fun sailing. - St Bart’s Bucket - Grenada Sailing Festival - Heineken Regatta – a Caribbean sailing and party Regatta – The Heineken St Maartens. - Here is the full list of Caribbean yachting and sailing events.

Other Caribbean Places to be:

- New Year’s Eve at St Barts Gustavia, St Martin and the BVI's - More info on Caribbean yachting and sailing events - Please see the Specific Caribbean location links on the left for more.

• Caribbean Charter Reviews
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Trina, Everything was perfect! The yacht, the crew, activities... The crew in particular was off the charts! They really did go out of their way to please us. Please release the full amount of the gratuity. I have nothing but good things to talk about the charter, an opinion shared amongst all of the guests. Thank you for all your help with the charter of Miracle, everything went smoothly and you were very professional and efficient during the whole process. I will not hesitate in contacting you for our next charter (next year, hopefully!!). Miracle BVI's charter (british Virgin Islands) Caribbean in April

Yachting Destinations Near the Caribbean

Explore Location Guides for great destinations near the Caribbean .

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Yachts for Charter in the Caribbean

112m freire superyacht | from eur€ 3,000,000/wk.

DREAM | From EUR€ 2,000,000/wk

95m LURSSEN MEGA YACHT | From EUR€ 1,600,000/wk

92M FULLY CUSTOM SUPERYACHT | From US$ 1,500,000/wk

93M FULLY-CUSTOM SUPERYACHT | From EUR€ 1,470,000/wk

83m Limited Editions 272 Superyacht | From EUR€ 1,200,000/wk

95 meter CUSTOM | From EUR€ 1,200,000/wk

86M CUSTOM LUXURY YACHT | From EUR€ 1,200,000/wk

ROMEA | From EUR€ 1,100,000/wk

80M MODERN CUSTOM YACHT | From EUR€ 1,085,000/wk

PHOENIX 2 | From EUR€ 1,000,000/wk

O'PARI | From EUR€ 1,000,000/wk

Caribbean Yacht News

Navigating the World of Luxury Yacht ...

37m luxury explorer yacht OCULUS brand ...

37m Gulf Craft Majesty superyacht ...

65m superyacht ETERNITY available for ...

The caribbean yacht charter specials, special offer location: caribbean/bahamas.

TC | From US$ 149,900.00/wk

15% discount location: caribbean.

AMIGOS | From US$ 250,750.00/wk

Charter yacht disclaimer.

This document is not contractual. The yacht charters and their particulars displayed in the results above are displayed in good faith and whilst believed to be correct are not guaranteed. CharterWorld Limited does not warrant or assume any legal liability or responsibility for the accuracy, completeness, or usefulness of any information and/or images displayed. All information is subject to change without notice and is without warrantee. A professional CharterWorld yacht charter consultant will discuss each charter during your charter selection process. Starting prices are shown in a range of currencies for a one-week charter, unless otherwise marked. Exact pricing and other details will be confirmed on the particular charter contract. Just follow the "reserve this yacht charter" link for your chosen yacht charter or contact us and someone from the CharterWorld team will be in touch shortly.

Caribbean yacht charters

• Best time to charter December - April
• Getting there Princess Juliana International Airport and more

Getting there

Caribbean charter bucket list

Caribbean Islands - discover the best by yacht

Party time!

The best Caribbean honeymoon islands

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Events in the caribbean.

St Barths Bucket

BVI Spring Regatta

Gourmet Festival

New Year’s Eve

Independence Day Carnival

International rolex cup regatta.

Crucian Christmas Festival

BVI Food Fete

Explore the caribbean.

Caribbean yachts available for charter

This is a small selection of the luxury motor and sailing yachts available to charter in the Caribbean. Please contact your Burgess broker for a personalised selection of Caribbean yachts for charter.

RENAISSANCE

Rate from USD 3,000,000 per week

• Length: 112m (367.4ft)
• 36 guests in 19 cabins
• Built: 2023, Freire Shipyard, Spain

Please enquire

• Length: 96.6m (316.8ft)
• 12 guests in 7 cabins
• Built: 2017 (refitted 2022), Feadship, De Vries Makkum, The Netherlands

Rate from USD 497,000† per week

• Length: 90.1m (295.6ft)
• 12 guests in 6 cabins
• Built: 2007 (refitted 2021), Corsair Yachts, China

Rate from USD 1,100,000† per week

• Length: 88.5m (290.4ft)
• 12 guests in 8 cabins
• Built: 2017, Oceanco, The Netherlands

MALTESE FALCON

Rate from USD 490,000 per week

• Length: 88m (288.6ft)
• Built: 2006 (refitted 2023), Perini Navi, Italy

Rate from USD 945,000† per week

• Length: 85.6m (280.9ft)
• Built: 2010 (refitted 2016), Derecktor Shipyard, United States Of America

Rate from EUR 550,000 per week

• Length: 81m (265.8ft)
• Built: 2020 (refitted 2022), Royal Huisman Shipyard, The Netherlands

Rate from USD 1,150,000† per week

• Length: 80m (262.5ft)
• Built: 2019, Abeking & Rasmussen, Germany

STARBURST IV

Rate from USD 870,000† per week

• Length: 74m (242.7ft)
• Built: 2017, CRN Ancona, Italy

Rate from EUR 520,000† per week

• Length: 73.5m (241.2ft)
• Built: 2008 (refitted 2013), Nobiskrug, Germany

New to charter?

Planning the perfect charter requires specialist knowledge, trusted contacts on board and on the ground, as well as first-hand knowledge of yachts, crews and locations, as well as legal contracts and local regulations to build an experience that suits you perfectly. Another reason to choose a broker is that sometimes there can be unforeseen issues with yachts or destinations and having an experienced broker to protect your interests and build a plan B is hugely reassuring. 

Creating the unforgettable is what we do at Burgess. It’s what our knowledge, experience and passion are all about. We take all the hassle out of the planning so you can just turn up and have the best holiday ever. 

Charter a yacht

Discover the Burgess difference

Charter a luxury yacht with Burgess. We are trusted for our expertise, and it is the first-hand insights of our charter brokers that raise the bar. Our collective knowledge serves to make your superyacht charter experience exceptional. Explore our stunning collection of luxury yachts for rent or hire and speak to our experts about chartering a private yacht to your dream destination.

Privileged access to the world’s finest charter yachts

Every charter yacht in the Burgess fleet is unique, from interior design and on board facilities, to watertoys and impeccable service. We rigorously inspect every yacht to ensure that when you find your ideal match, it exceeds every expectation.

A wealth of knowledge to enhance your experience

A superyacht charter offers life-affirming adventure and little can compare to a tailor-made experience orchestrated by your Burgess broker. By accommodating both your preferences and requirements, no detail is left to chance.

Personalised service that goes above and beyond

Burgess charter brokers are involved well beyond the booking stage. We share our intelligence on the best itineraries to suit you, organise private jet transfers, on board celebrations, luxury boat hire, restaurant bookings, spa treatments, fitness instruction and more.

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Home ~ Charter Destinations ~ Caribbean

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What does 'All Inclusive' mean?

All inclusive rates typically include: all your breakfasts, lunches, dinners, snacks and Standard Ship's Bar, which includes your alcoholic and non alcoholic beverages. Excluded are airport transfers costs, onshore excursions and tours, as well as any food or beverages purchased ashore. Although optional, crew gratuity is customary at 15% - 20% of the charter rate for the Caribbean and 10% - 15% for the Mediterranean. *Inclusions and exclusions vary by yacht, as each offers unique terms. Please contact us for a custom proposal that details the yacht’s availability, pricing, as well as the list of the inclusions and exclusions for that particular yacht.

What does 'Plus Expenses' mean?

Included are the Yacht and its onboard equipment as well as the Captain, Chef and Crew’s services.Excluded are food and beverages, fuel for the yacht and its tender, any dockage, airport transfers costs, onshore excursions and tours, as well as any cruising permits, licenses and other charter related expenses. Crew gratuity, although optional is customary at 15% - 20% of the charter rate for the Caribbean and 10% - 15% for the Mediterranean. *Inclusions and exclusions vary by yacht, as each offers unique terms. Please contact us for a custom proposal that details the yacht’s availability, pricing, as well as the list of the inclusions and exclusions for that particular yacht.

The Best Crewed Yachts ‍ For Your Perfect Vacation.

Plan Your Next Adventure

Book an unforgettable yacht charter vacation.

Sail Play Dine Yacht Charters is here to help you plan a trip you’ll never forget. Experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed charter yacht in the US and British Virgin Islands, Bahamas, and beyond! We take care of your every need to match you with the right boat and crew at the best rate guaranteed. We offer a large range of boats that suit every budget and our trusted service comes at no extra cost to you!

How it Works

Tell us about your perfect vacation. Destination, preferences, budget, who will be joining you, and what you would like to see and do.

Our team will be in touch with an initial proposal that we’ll refine together. The yacht charter vacation proposal will include our top recommendations tailor-made to match your interests.

Once you decide on your preferred yacht, we can put a complementary hold to secure your dates while you finalize your travel plans. Complete your reservation by paying a deposit fee.

Featured Yachts

The best crewed yachts carefully vetted by our team.

Special Offer

Plus Expenses

Plus Expenses Charters generally don't include food and beverages as well as fuel for the yacht. Inclusions and exclusions vary by yacht, please contact us for a custom proposal.

All Inclusive

All Inclusive Charters typically include food and beverages you consume in the yacht. Inclusions and exclusions vary by yacht, please contact us for a custom proposal.

Book with Confidence.

This was one of the very best trips we’ve ever taken and by far the best vacation we’ve taken in the Caribbean.  We have been to many islands and resorts over the last 30 years; all wonderful experiences, but pale in comparison to this vacation.

Beatriz was great in assisting us to choose the right catamaran for 8 of us including two kids on relative short notice and very helpful In answering all kinds of question about the boat, the crew , contract and the possible route.Definitely recommend you use their expertise in choosing your boat and crew  as I will also do the next time I do a charter in the islands .

Jorge Canellas

Fabiola took all the time I needed to choose the perfect yacht vacation for my friends and I for my special birthday.  In the end, all of my needs were met and we had the vacation of a lifetime.  She was extremely patient in explaining all the ins and outs and what to look for as I was choosing the perfect yacht and I so appreciate that.  She also made all the paperwork and pre-vacation planning a breeze.  Thank you Sail Play Dine Yacht Charters!

Esther Kuznetz

Beatriz & Sail Play Dine was wonderful to work with. Top notch service and answered my endless questions regarding this type of vacation that was completely new to me. I highly recommend them!

Karen Skayhan

Why Choose Sail Play Dine?

Our trusted service comes at no extra cost to you! Our commission is paid by the yacht owner and there is no additional cost to you.

Our recommendations are personalized and hand selected. We look forward to working with you to make the right choice.

We are with you every step of the way. Before, during and after your vacation, to make sure it is unforgettable. We are available 24/7 by phone, text, whatsapp, social media or email. Or you could send us a message in a bottle, and we’d respond to that.

Where would you like to go

Incredible destinations, tailored to your dream vacation.

Download the ultimate all-inclusive yacht charter vacation guide.

Discover the top tips for planning your perfect dream vacation

Frequently Asked Questions

Absolutely! In fact, we recommend it. This type of vacation is typically booked 12-18 months in advance, especially when booking during school vacation (Spring Break) and holidays (Christmas and NYE).

Yes, you can! While most charter yacht pricing is based on a weeklong charter, some yachts offer daily rates, allowing you to customize the duration of your trip. However, please note that some yachts may apply a surcharge for charters shorter than 6 nights. The flexibility of charter durations varies by yacht. We’ll discuss your specific needs and give you recommendations.

The Caribbean is a great destination year-round. Temperatures range from around 79°F in December to March to around 84°F from May to October. Winds are slightly higher in winter, and rates may be higher during holiday weeks, particularly from Thanksgiving through Easter. Christmas and New Year's charters are often booked well in advance.

It's unlikely. The rates on Sail Play Dine are provided directly by the charter yacht management. We are promptly informed of any discounts or special offers. Our team at Sail Play Dine maintains strong relationships with all yacht agents. If you're looking for a better rate, contact us, and we'll work with the agents on your behalf to explore available options.

Crewed yacht charters range from $20,000 to $100,000 per week, depending on the yacht's size, age, and capacity. Fees may be all-inclusive or include additional running expenses and APA (Advanced Provisioning Allowance) for luxury motor yachts.

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All prices are subject to change and are based on availability.

US Virgin Islands

A USVI yacht charter is a perfect blend of laidback relaxation, sophisticated shopping and dining, quaint towns, turquoise waters, stunning beaches and landscapes full of adventure.

Virgin Island Sailing® can help you book the ideal USVI yacht for your sailing vacation.

Speak to a Charter Expert: (800) 382-9666 REQUEST A QUOTE

Easy Wind Bareboat Charter in US Virgin Islands

• 35.3 Length Total
• 2 Cabins Total
• 2 Max. Guests
• Waypoints Yacht Charters
• Yacht Type: Sailing Monohulls
• Yacht Age: 2023
• Manufacturer: Dufour
• Model: Dufour 37 - 2 cab.
• Air Conditioning
• Water Maker

MY IRISH LADY Bareboat Charter in US Virgin Islands

• 38.4 Length Total
• 3 Cabins Total
• 6 Max. Guests
• Virgin Islands Yacht Charters
• Yacht Type: Sailing Catamarans
• Yacht Age: 2020
• Manufacturer: Leopard
• Model: Leopard 39

Infinite Blue Bareboat Charter in US Virgin Islands

• 38.5 Length Total
• 4 Cabins Total
• 8 Max. Guests
• Manufacturer: Fountaine Pajot
• Model: Fountaine Pajot Lucia 40

QUARDA JEEPI Bareboat Charter in US Virgin Islands

• 39.1 Length Total
• 11 Max. Guests
• Dream Yacht Charter
• Yacht Age: 2022
• Model: Fountaine Pajot Isla 40 - 4 + 1 cab.

Island Curtisea Bareboat Charter in US Virgin Islands

• 4 Max. Guests
• Model: Fountaine Pajot Isla 40 - 4 cab.

TOLKIEN II_DB Bareboat Charter in US Virgin Islands

• 39.3 Length Total
• 10 Max. Guests
• Yacht Age: 2018
• Manufacturer: Catana
• Model: Bali 4.0 - 4 cab.

NOBLE SHADOW 2 Bareboat Charter in US Virgin Islands

• 40.0 Length Total
• Model: BALI 4.0

NANCYE IV Bareboat Charter in US Virgin Islands

• 40.4 Length Total
• 7 Max. Guests
• Model: Bali Catspace OW

SADALBARI _DB Bareboat Charter in US Virgin Islands

• 40.8 Length Total
• Manufacturer: Beneteau
• Model: Oceanis 41.1

CALYPSO Bareboat Charter in US Virgin Islands

• 41.0 Length Total
• 5 Cabins Total
• Model: Astrea 42

SeaSea Bareboat Charter in US Virgin Islands

• 41.3 Length Total
• Model: Fountaine Pajot Astrea 42

KRUZEN Bareboat Charter in US Virgin Islands

• 42.0 Length Total
• Yacht Age: 2021

BELLATRIX Bareboat Charter in US Virgin Islands

• 9 Max. Guests
• Manufacturer: Lagoon
• Model: Lagoon 42 - 3 + 1 cab.

BELIEVEN Crewed Charters in US Virgin Islands

MIMBAW Crewed Charters in US Virgin Islands

• Yacht Age: 1999

MIMBAW Captain Only Charters in US Virgin Islands

MOONGLADE Bareboat Charter in US Virgin Islands

• 42.2 Length Total
• Model: Bali 4.2 OW

UNCHARTED Bareboat Charter in US Virgin Islands

• Model: Bali 4.2 - 4 + 1 cab.

Request Confirmation

Terms and conditions, charter experts, llc terms & conditions.

PLEASE READ THESE TERMS AND CONDITIONS (“ Terms ”) CAREFULLY AS THEY CONTAIN IMPORTANT INFORMATION REGARDING YOUR LEGAL RIGHTS, REMEDIES AND OBLIGATIONS AS WELL AS A SECTION GOVERNING THE JURISDICTION AND VENUE OF DISPUTES. THESE TERMS ALSO CONTAIN A LEGALLY BINDING RELEASE, WAIVER OF LIABILITY, AND ASSUMPTION OF RISK. By creating a username, a login, clicking submit, using the services of Charter Experts, LLC d/b/a Virgin Island Sailing® (“ Broker ) or by accessing Broker’s website, you agree that you have read, and acknowledge your acceptance of these Terms. The Terms are subject to change at any time without notice at Broker’s sole discretion. Additionally, any transaction for which you have made payment shall be governed by the form of Terms in effect at the time of such payment notwithstanding any subsequent changes hereto.

If you are obtaining a quote, information, booking travel for and/or securing or procuring a Charter (as that term is defined in Section 1 below) for more than just yourself, all references below to “Charterer” or “you” (and derivations thereof) shall be read to mean you on behalf of yourself and each individual within your group for whom you are obtaining a quote, information, booking travel for and/or securing or procuring Charter.

These Terms shall be read together and construed, to the fullest extent possible, to be in concert with any other agreement by or among Broker and Charterer. To the extent they cannot be so construed, then in the event of any direct conflict between these Terms and any other agreement by or among Broker and Charterer (including but not limited to the agreement executed by Charterer for a Charter Reservation (as that term is defined in Section 1 below), these Terms shall prevail.

• Prepaid Charter Reservations . Typically, Broker negotiates charter rates in advance with the yacht owner or charter company (“ Charter Provider ”) to obtain cost-effective rates, and facilitate reservations and availability for yacht charters, excursions and travel (the “ Charter ”). Broker also provides services to you by facilitating the booking of reservations for consideration and receives a commission from the Charter Provider (the “ Broker Fee ”). The Broker Fee is included in the pre-negotiated Charter rate provided to you, plus taxes and other fees where applicable. You agree that your payment is for the total amount set forth in the applicable Charter agreement (which Charter Provider may refer to as a Charter Contract, Charter Agreement, Booking Terms & Conditions, Instructions and Terms for Accommodations, as well as other derivations) provided to you by Broker (“ Charter Agreement ”). Upon execution of the Charter Agreement and receipt of the applicable deposit, you will have made a reservation for the Charter that authorizes Broker to facilitate the Charter on your behalf (“Charter Reservation”), including making payment arrangements with the Charter Provider. You further agree that Broker is a third-party beneficiary to the Charter Agreement and shall have the right to enforce such agreement to the extent it deems such enforcement necessary or advisable to protect its rights hereunder or under the Charter Agreement.

  Broker retains the Broker Fee as compensation in arranging your Charter Reservation. The Broker Fee varies based on the amount and type of Charter and/or services provided by Broker.  By making a Charter Reservation, you accept and agree to the relevant cancellation and no-show policy of the Charter Provider set forth in the Charter Agreement. Cancellation and no-show policies vary for each Charter. Carefully read the Charter Agreement and additional information provided to you by Broker. It is expressly agreed by Charterer that the Broker Fee is earned at the time the Charter Reservation is made. Late payment, wrong credit card or debit card details, invalid credit or debit cards, or insufficient funds are for your own risk and account, and you will not be entitled to any refund of any prepaid amount unless the Charter Provider expressly agrees otherwise under the Charter Agreement or in some other signed writing.

• Charter Rules and Restrictions . Additional terms and agreements will apply to your Charter Reservation and any purchase or rental of equipment or other items, supplies, provisions and travel you may select. Please read those additional terms carefully. In particular, if you have purchased airfare, please ensure that you read the full terms and conditions of carriage issued by the supplier. You agree to abide by the terms of purchase imposed by any supplier with whom you elect to deal, including but not limited to payment of all amounts when due and compliance with the supplier’s rules and restrictions regarding availability, charges, fares, and use of products and services.
• Payment . All payments must be made by personal check, bank/wire transfer, ACH payment and/or with a major credit card unless otherwise expressly stated. The total price for the Charter Reservation will be billed in U.S. Dollars unless otherwise stated. Some banks and credit card companies impose fees for international transactions. If you are making a reservation from outside of the United States on a US credit card, your bank may convert the payment amount to your local currency and charge you a conversion fee. This means the amount listed on your credit or bank card statement may be in your local currency and therefore a different figure than the amount provided by Broker for the Charter Reservation. In addition, a foreign transaction fee may be assessed if the financial institution that issued your credit card is located outside of the United States. Booking international travel may be considered to be an international transaction by the financial institution or card company. The currency exchange rate and foreign transaction fee is determined solely by your financial institution on the day that it processes the transaction. If you have any questions about these fees or the exchange rate applied to your booking, please contact your financial institution. Broker shall not be liable to you for any such service, conversion, or exchange fee.

  Broker expressly reserves the right to cancel your Charter Reservation if full payment is not timely received as set forth in the Charter Agreement.

• Cancellation and Rescheduling . You may cancel or change your Charter Reservation as set forth in the Charter Agreement by and among you, the Charter Provider and/or Broker. Please note that some Charter Providers do not permit changes to or cancellation of reservations after they are made, or after a certain date, as indicated in the Charter Agreement. You agree to abide by the terms of the Charter Agreement with respect to your Charter Reservation. Broker will not be responsible for reimbursing Charterer for any previously tendered deposits or payments by Charterer and disclaims all liability for the failure of a Charter Provider to refund or return any such funds.
• Credit Card Transactions and Chargebacks . If for any reason, any Charter Provider is unable to provide the Charter, or any part thereof, for which you have contracted, your remedy lies against the Charter Provider, and not against Broker. However, Broker will use reasonable efforts to assist you and Charter Provider in reaching a resolution to a dispute between you and the Charter Provider. In the event that your payment has already been transferred from Broker to Charter Provider or to an escrow account, you agree that you will not seek a chargeback against Broker for such amounts transferred. You further agree to indemnify and hold Broker harmless from and against any liability, loss, damage or expense (including without limitation, reasonable attorneys’ fees) that Broker may incur in connection with chargebacks against Broker or under the Charter Agreement and your performance thereunder. If Broker incurs any costs, including but not limited to attorneys’ fees, to recover any payments charged back by your credit card company or other financial institution, you agree that you will be liable for these costs. If your payment is declined for any reason, you agree to settle any amounts owed to Broker via money order, cashier’s check, personal check or bank/ACH transfer immediately.
• Broker Responsibility . Broker makes arrangements with the Charter Provider. Broker additionally makes additional arrangements with other suppliers for the various components and other services that comprise your Charter (“Charter Suppliers”). Broker is not an agent of these Charter Providers or the Charter Suppliers (and the Charter Providers and Charter Suppliers are not agents of Broker). Broker expressly disclaims any liability for the actions or omissions of the Charter Provider and the Charter Suppliers. The Charter Providers and the Charter Suppliers reserve the right to refuse service to you at their sole discretion. Broker assumes no liability for the acts of the Charter Provider or the Charter Suppliers in refusing service. Broker is not responsible for schedule changes and does not offer compensation for those changes. Broker is not responsible under any circumstances for any injury or damages you may suffer, in connection with sea, air or ground transportation, hotel accommodations, or other travel or excursion services arranged by Broker.

  You understand Broker is not the source or supplier of the Charter or other travel services you requested and acts solely as a broker for the Charter Provider and the Charter Suppliers. You agree that the Charter Provider and Charter Suppliers whose names appear in the information supplied to you are those who are solely responsible for providing the Charter you purchase. You consent to and request the use of the Charter Provider and the Charter Suppliers and agree to not hold Broker responsible should any of them: (i) fail to provide the Charter or travel services you purchased, whether or not such services are listed in the Charter Agreement or otherwise, (ii) fail to comply with any applicable law, or (iii) engage in any negligent act or omission that causes you any sort of injury, damage, delay or inconvenience.

By using Broker’s services, you waive and release any claim against Broker, its affiliated and subsidiary companies, and their respective officers, directors, employees, contractors, and agents, arising out of or in connection with any loss of or damage to property or injury to any person caused by reason of (i) any defect, negligence, or other wrongful act or omission, or any failure of performance of any kind, by any Charter Provider, Charter Suppliers, or any other provider of sea, airline, hotel, ground transportation or any other travel provider connected to or otherwise associated with the Charter, (ii) any claim for inconvenience, loss of enjoyment, mental distress or other similar claim, (iii) any delayed departure, missed connection, substitute accommodation, termination of service or change in fares or rates, and (iv) overbooking, flight or other travel cancellation, lost or misconnected personal property, or any claim arising out of the air transportation portion of your travel, and (v) or any other claim arising out of or otherwise related to the Charter Agreement or services provided by the Charter Provider and the Charter Suppliers.

Excepting only liability that directly arises from the gross negligence or willful misconduct of Broker, you will not hold Broker responsible for any injury, damage or loss you may suffer while on a Charter, whether incurred on the Charter or in connection with any other rental, purchase, excursion or activity, regardless of the relationship of any of the foregoing with the Charter Provider or the Charter Suppliers.

• Your Responsibility . By booking a Charter with Broker, you agree to defend and indemnify and hold harmless Broker, Charter Provider, Charter Suppliers, and each of their respective officers, directors, employees and agents, from and against any and all claims, causes of action, demands, recoveries, losses, damages, fines, penalties or other costs or expenses of any kind or nature, including but not limited to reasonable legal fees, arising out of or in connection with: (i) your breach of these Terms or the documents referenced herein; (ii) your violation of any law or rights of a third party; or (iii) your use of the Broker website.

You will review your Charter Agreement and travel documents for accuracy upon receipt. You understand that it is your responsibility to review the accuracy of all details in the Charter Reservation provided to you, and that you may contact Broker if you have any questions.

You assume full and complete responsibility for checking and verifying any and all passport, visa, vaccination, or other entry requirements of your destination(s), and all conditions regarding health, safety, security, political stability, and labor or civil unrest at such destination(s).

You understand that Broker recommends purchasing travel insurance to cover certain risks inherent in travel such as supplier bankruptcy and the inability to travel due to a medical or personal emergency.

• No Warranties . All Charters, products, services, advice and information is provided on an “as is” and “as available” basis without warranties of any kind, either expressed or implied to the fullest extent permitted under the law, including but not limited to, warranties of title or implied warranties of merchantability, satisfactory quality or fitness for a particular purpose. Without limiting the above, no warranty or guarantee is made (i) regarding the acceptance of any reservation request or Charter Reservation; (ii) regarding the availability of Charters, or any other product and/or services through Broker; (iii) that the use of Broker’s website will be error-free; or (iv) regarding the completeness, accuracy, reliability or quality of any information, content, data, service, advice or merchandise provided by Broker or through Broker’s website.

Broker has no special knowledge regarding the Charter Provider’s or Charter Supplier’s financial condition, unsafe conditions, health hazards, weather hazards, or climate extremes at locations to which you may travel during or otherwise in connection with your Charter.

• Limitation on Liability . In no event shall Broker, Charter Provider, Charter Suppliers, and/or their respective affiliates, or any employees, agents, officers, directors, members or managers of any of the foregoing (“Broker and Charter Releasees”), be liable for any direct, indirect, punitive, incidental, special or consequential damages arising out of, or in any way connected with, your access to, display of or use the Broker’s website, the Charter or services provided to you in connection with the Charter (including, but not limited to, your reliance upon opinions of the Broker), whether based on a theory of negligence, contract, tort, strict liability, consumer protection statutes, or otherwise, and even if Broker and/or any other of the Broker and Charter Releasees have been advised of the possibility of such damages.

If, despite the limitation above, Broker or the Broker and Charter Releasees are found liable for any loss or damage which arises out of or in any way connected with any of the occurrences described above, then Broker, Charter Provider, Charter Supplier and the Broker and Charter Releasees will in no event exceed, in the aggregate, the greater of (a) the Broker Fee, and (b) One-Hundred Dollars (US $100.00).

The foregoing limitation of liability reflects the allocation of risk between the parties. The limitations specified in this section will survive and apply even if any limited remedy specified in these Terms is found to have failed of its essential purpose. The limitations of liability provided in these Terms inure to the benefit of Broker and/or its providers.

The foregoing does not affect any liability which cannot be excluded or limited under applicable law.

• Limitation on Time to File Claims . ANY CAUSE OF ACTION OR CLAIM YOU MAY HAVE ARISING OUT OF RELATING TO BROKER’S SERVICES OR THE WEBSITE MUST BE COMMENCED WITHIN ONE (1) YEAR AFTER THE CAUSE OF ACTION ACCRUES, OTHERWISE, SUCH CAUSE OF ACTION OR CLAIM IS PERMANENTLY BARRED.
• Waiver . No waiver by Broker of any term or condition set forth in these Terms shall be deemed a further or continuing waiver of such term or condition or a waiver of any other term or condition, and any failure of the Broker to assert a right or provision under these Terms shall not constitute a waiver of such right or provision.
• Severability . If any provision of these Terms is held by a court or other tribunal of competent jurisdiction to be invalid, illegal or unenforceable for any reason, such provision shall be eliminated or limited to the minimum extent such that the remaining provisions of the Terms will continue in full force and effect.
• Governing Law and Mandatory Venue . The laws of the State of Florida govern the rights and obligations of the parties to this Agreement and the interpretation, construction and enforceability thereof. You agree that any action or proceeding initiated by Charterer against Broker shall be brought solely in the federal and state courts of Hillsborough County, Florida, and you submit to the jurisdiction of those courts and waive any objections to the exercise of personal jurisdiction over you by those courts. In the event any action or proceeding is initiated by Charterer in a court outside of Hillsborough County, Florida, Charterer agrees to pay Broker’s costs and reasonable attorneys’ fees associated with defending such action or proceeding and waives any and all defenses to the transfer of said action or proceeding, whether jurisdictional or otherwise, to a federal or state court in Hillsborough County, Florida.

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11 of the Best Places to Sail In the Caribbean – For Your Charter Vacations

The Caribbean region is undeniably one of the best yachters’ playgrounds there is in the world. And there are several reasons for that. Aside from the charming tropical landscape, crystal clear waters, and powdery-soft sandy beaches, the region is endowed with pleasant weather all year round and boasts vibrant, diverse cultures.

Whether you would wish to sail on a crewed or bareboat charter , hopping from one island to the next in the Caribbean can be exciting, adventurous, and rewarding.

But do you really know where to take your sailing vacation in the region? Well, here is a list of the  best places to sail in the Caribbean , which you’ll find truly inviting:

Table of Contents

Perhaps the best-unnoticed boating paradise in the Caribbean, Guadeloupe is a group of islands on the Eastern Caribbean, all of which offer an unimaginable number of delights to sailors.

Of the six islands of Guadeloupe, Basse-Terre and Grand Terre are among the largest. While the former is known for its lush green forests and mountainous landscape, the latter boasts of flat, dry terrain with lots of touristic beaches.

The rest of the islands are uninhabited and relatively untouched and can be great to explore too. But the islands of Basse-Terre and Grand Terre, with a rich Franco-Caribbean culture and history, are an absolute favorite for most sailors.

Chartering a boat and exploring the Guadeloupe archipelago is an experience that can turn out to be fun and memorable, especially if you’re visiting the Caribbean for the first time.

St. Lucia is an Eastern Caribbean island that has a charm that can be found nowhere else in the region. Right from the dramatically tapered mountains to its inviting volcanic beaches through to the amazing reef-diving sites and fishing villages, there’s more than enough to explore here as a sailor. While St. Lucia is a relatively small tropical gem, it has excellent spots for diving, snorkeling, rainforest hiking, bird watching, and more, which you’ll highly appreciate while chartering.

British Virgin Islands

The British Virgin Islands (BVI) is regarded by many as the top sailing destination in the Caribbean and the world at large for multiple reasons. Some of the prime reasons include the mild and reliable trade winds, the countless scenic beaches with boulders, and the short distance between islands.

Tortola, Jost Van Dyke, Peter Island, Virgin Gorda, Anegada, and Norman Island are a few of the islands on the archipelago that have won the hearts of many because of their great sailing opportunities.

Dubbed the birthplace of bareboat chartering, BVI has a well-established sailing infrastructure and amazing beach restaurants that can satisfy every yachter’s need. Hence it is a perfect spot in the Caribbean to go to for a first sailboat experience or a catamaran charter adventure.

Apart from snorkeling and windsurfing, there are other fun activities to indulge in within the islands, like visiting the Virgin Gorda Baths, exploring the Deadman’s Bay at Peter Island, and interacting with the locals.

Strategically located between France and Netherlands, St Martin is a small yet popular island when it comes to sailing. In fact, it is one of the most amazing spots there is in the Caribbean for regattas. The part of the island that is on the French territory boasts multiple secluded beaches, several plush accommodations, and a sizable number of first-class restaurants. On the other hand, the Dutch side is known for its festive nightlife and scenic beaches.

Stretching 120 miles long, the Abacos features a chain of islands that boast calm waters, panoramic landscapes, and warm breezes. The long stretch also has beautiful bays, coves, and well-protected harbors with full-service marinas and resorts.

This makes Abacos a coveted boating and sailing paradise. But the fun doesn’t stop at sea; there are a couple of colonial towns, world-class golf courses, and countless hotels & restaurants that can spice up any yacht charter’s adventure.

Dominica is a nature island that features dramatic coastal scenery, luscious rainforests, free-flowing rivers, and relaxing thermal springs. The natural beauty of the island remains untouched, and chartering is the best way to behold the beauty of the rolling hills and experience the charm of the secluded coastlines.

Anguilla & St Barts

St Barts is a unique gem that boasts 20 exotic white sandy beaches on its shoreline. Most of the beaches here boast spectacular coral reefs, and there are some that feature offshore Marine Reserves.

St. Barts is a yachters’ paradise that’s well known for hosting superyachts. Many celebrities come to the island to unwind and enjoy the region’s French-inspired culture as well as tasty cuisines. 

Further north lies Anguilla, a territory that proffers its visitors a range of fresh seafood, whose preparation is inspired by Caribbean, French, British, and Spanish styles of cooking. With things to explore in one go, the sailing experience here will most certainly be rewarding.

Stretching through the nations of St Vincent and the Grenadines and Grenada, Grenadines is a chain of islands that promises to offer sailors a full range of authentic Caribbean experiences. 

The islands of Bequia, Mayreau, Union Island, Carriacou, and Tobago Cays are known for their impressive barrier reefs, quintessential marine parks, and relaxing beaches. The opportunities to sample fresh seafood and experience diverse local cultures along these islands also exist in abundance.

Mustique and Canouan Islands, on the other hand, are private islands famous for their pricey accommodations, quiet beaches, and low-key sailing environments.

They also boast of first-class snorkeling spots that can be super fun to explore. So regardless of the sailing experience you’re looking for in the Caribbean, the Grenadines has it all.

Antigua & Barbuda

Located in the Eastern part of the Caribbean, Antigua and Barbuda are among the famous charter destinations in the region. The two islands consist of 365 pristine beaches with innumerable anchorages and harbors that make them an enticing paradise for sailors.

Barbuda is famous for its magnificent snorkeling spots and incredible bird sanctuary, while Antigua has lots to offer in terms of secluded powdery-soft beaches, beautiful bays, and unimaginable coral reefs.

Lying south of the Grenadines, Grenada is a rolling, mountainous island that’s well-known for its crystal-clear waters, Volcanic black & white coastline as well as stunning coral reefs.

The early cultural influences of the islands had influences from Europe and South America, something that’s reflected in the local language and cuisine. Grenada’s weather is consistently warm throughout the year, even in the months of August and September when tropical storms are at their highest.

The islands are also equipped with protected harbors and boast good anchorages too. That, plus the superb accommodation around, makes Grenada a top choice for any charterer wishing to sail the Caribbean.

The Spanish Virgin Islands

Located about 10 miles off Puerto Rico, the Spanish Virgin Islands are famous for their mellow environment and laid-back atmosphere. The Spanish Virgin Islands are made up of the charming Vieques and the alluring Culebra. 

Vieques is the home of lush, unscathed Caribbean beauty and offers a perfect playground for diving, biking, horseback riding, and hiking, among other nature-inspired activities.

Culebra, on the other hand, has a reasonable amount of water depths that are just ideal for snorkeling and scuba diving. The island also boasts hard and soft corals that are coupled with tropical fish and other sea life to make the underwater experience unbeatable.

With such an amazing list of places to visit in the Caribbean, you can almost be spoilt for choice on where to take your upcoming yacht charter vacation to. But since each of the islands has something unique to offer, you can never miss finding one that perfectly suits your sailing needs.

One important thing you should know is that you don’t have to own a yacht or have sailing skills to cruise the region. There are many options like bareboat charter, luxury yacht charter and crewed yacht/catamaran charter that you can take advantage of for a fun and adventurous sailing experience.

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Do you know other beautiful places to sail in the Caribbean? If so, you are welcome to share them in the comments below.

Daniella has been passionate about travel, the sea, and nature for many years. As a child, she frequently traveled throughout the Mediterranean and continued with her journeys throughout her adult life.

Her experiences have created the desire within her to share her love for traveling with other passionate and adventurers who want to discover beautiful horizons and new cultures.

12 thoughts on “11 of the Best Places to Sail In the Caribbean – For Your Charter Vacations”

Out of all the destinations you have covered here in the article above, I would really love to someday visit the islands of Guadeloupe, as my auntie went there when I was a kid and brought back wonderful pictures with her. 

I don’t know what it is, but I prefer the more ‘untouched’ holiday destinations as opposed to the more traditional urban destinations. Islands always seem more exciting than a hotel full of tourists! 

Hi Chris, I agree with you, being in a crowded hotel is not really relaxing vacation. The good thing about chartering a yacht is that you can sail to uninhabited islands and enjoy every moment without being surrounded by thousands of tourists.

Thank you for the comment and I hope you have a fantastic day!

Hi that’s a beautiful review of the Caribbean. Your visuals bring the whole post to life for sure. I personally like st.lucia and hope I can take my family there in the not too distant future. Thank you so much for showing tour site viewers these terrific places and I hope to check out future reviews from you soon. Kenny 

Thank you for passing by and I wish you to sail very soon to the Caribbean with your family:)

Have a nice day!

That’s an excellent list of amazing destinations to visit.  My first choice would be the British Virgin Islands followed by the Spanish Virgin Islands. I am a great fun of travelling but have not tried the yacht yet.  Do you have sea travel tips for the first time travelers? I intend to take the yacht in the coming year.

Great choices, the BVI and the Spanish islands are beautiful, especially when visited by boat! Yes, there are a few useful articles for first-time travelers on the water:) Please, take a look at these: How to plan a sailing trip – How to book a boat .

If you need help with something, don’t hesitate to contact me. I am happy to assist:)

Thank you for the comment and wish you a fantastic day!

A dream of mine is to one day own my on yacht and sail. The pictures and views from these yachts are spectacular and more than what I imagined I love the ocean and the views from the sea. I am bookmarking this site and will be revisiting to get inspiration of the places that I will want to travel to one day. 

Hi Richard,

That’s a wonderful dream! Thank you for bookmarking my website, I really appreciate, thank you!

I wish you a lovely day!

Wow!!  The caribbean is really beautiful filled with breath taking views, I can tell from the lots of pictures. on the internet I haven’t been there yet..we’re still making the Benjamins hopefully we would tour the Caribbean someday. Thanks for bringing this amazing destinations to your readers

Please I would like you to write about the cost of various cruise around the Caribbean whatis the financial implications.  I know this might be challenging but it quite important

Yes, the Caribbean is a unique place, a kind of paradise:)  It’s difficult to say the exact price of a yacht charter as prices vary depending on the destination, the type of charter, the duration and many other factors.

Hi! I have always been impressed by the cultural diversity that exists in the Caribbean. Although all these Islands have pristine clear waters, no two islands are the same culturally.

Thank you very much for this list. In my personal choice I pick Antigua & Barbuda. In your experience, which would be the best time of the year to visit the Caribbean?

You are very welcome! Great choice! Antigua and Barbuda are stunning! The Caribbean is a winter destination and the best time would be between December to May. At these periods of the year, the wind is relatively calm, and the weather is pleasant. It’s the best time to sail there. 

Thank you for the comment, and I hope you have a nice day!

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Caribbean Sailing Vacations

Fine white sandy beaches, palm trees swaying in the warm breeze and a shimmering cobalt sea like you’ve never seen before. Experience Caribbean yacht charters and banish those winter blues...

Fine white sandy beaches, palm trees swaying in the warm breeze and a shimmering cobalt sea like you’ve never seen before. Boating trip from the archipelagos of the British Virgin Islands or US Virgin Islands sailing to the diverse cultural differences of the Windward and Leeward Islands, there is something for everyone. Discover some of the world’s best scuba and snorkelling, welcoming smiles and, of course, perfect beaches on a Caribbean sailing vacation.

Wherever you choose to go, you’ll find a Sailo boat rental to make your visit unforgettable. After all, the Caribbean looks great from the beach, but to really enjoy the region in all it’s tropical beauty, take to the seas!

Great sailing conditions

The islands of the Caribbean are well known as a world class nautical playground, with great opportunities for exploring by boat all year round. One of the most popular ways to explore the region is with a private yacht charter, meaning more space on deck to relax and soak up the sun and escape the crowds.

You’ll find Caribbean luxury yacht charters with Sailo to match your style, vacation plans and budget. Choose from luxury motor yachts, beautiful classic sailboats and catamarans, or hop aboard a thrilling speedboat ride for a day on the sea.

Enjoy island hopping and exploring hidden bays, set sail to uninhabited cays and islands, or simply hire a boat for a day trip, a private party boat or fishing charter. From a budget friendly sailing vacation, to an indulgent luxury experience, a Sailo yacht charter will fulfil your Carribean dreams.

Discover the Caribbean your way

The Caribbean islands each have their own character, with a mixture of different colonial influences blending with local traditions. From the French flavors of Guadeloupe and Martinique, to the quirky British traditions of Bermuda, Barbados and the BVI's.

With a week long Caribbean catamaran charter, you have full control and can take your time to get to know the region, arriving in style to a new port every day. Get adventurous and find your dream tropical island, jump into that shining sea and say “Hi” to the locals swimming around the plethora of coral reefs. By night, escape and relax, enjoy a sundowner from the deck of your Sailo yacht charter and toast another perfect day in the Caribbean!

Whether you’re looking for a captained yacht, or a bareboat catamaran or sailboat, browse Sailo for your dream Caribbean yacht charters.

The British Virgin Islands (BVI)

Tropical paradise doesn’t come much more stunning than the British Virgin Islands in the eastern Caribbean Sea. This British overseas territory offers the opportunity to find some of the most unspoiled and beautiful landscapes in the region. Jost Van Dyke offers many sheltered bays and is dotted with beautiful hidden beaches. Enjoy lunch at one of the relaxing bars or restaurants and top it off with a visit to ‘Bubbly pool’, the island's naturally foaming sea pool!

With a Sailo yacht or catamaran charter, explore this stunning Caribbean destination at your leisure. Coast hop around Tortola, the biggest island, visit the Little Sisters, or head to remote Angeada for true seclusion.

The US Virgin Islands (USVI)

The US Virgin Islands have an unmistakably American flavor and attract American families escaping the winter and looking for some fun in the sun. When it comes to sailing vacations, the USVI’s offer a fantastic choice of locations for Caribbean boat charters.

St. Thomas is known as a premier yacht charter marina in the Caribbean and offers a host of beautiful beaches and snorkelling opportunities. Why not support local business with one of Sailo’s family run private boat tours and head to Brewer’s bay for some of the best snorkeling and a chance to see Turtles and rays.

Get on one of the yacht charters in St. Thomas and cruise to Frydendal, small laid-back settlement of serene beaches and rich marine life. Coki Beach provides some of the best diving on the island. For more adventure places in USVI, explore the famous Wreck of Cartanza, at Shipwreck Cove on Buck island. Just one of the many stunning shipwrecks and coral reefs you can discover by snorkel or scuba in the USVI's.

Strictly speaking Bermuda isn’t in the Caribbean, but she maintains that tropical vibe. Lazy days on beautiful pink sandy beaches, fantastic fishing and friendly and laid back locals. To all intents and purposes, this is the Caribbean! Sailing in Bermuda means less in the way of island hopping, and more fishing charters or exploring shipwrecks with snorkels or scuba gear. With a Bermuda private yacht charter you can explore the many islets along the coast and enjoy an unforgettable game fishing trip.

The Windward Islands

The southern section of the Antilles includes St Lucia, Grenada, Barbados, Martinique, Trinidad and Tobago and St Vincent and the Grenadines. These islands offer diverse Caribbean experiences, and a mixture of cultures and landscapes. The southern Caribbean also sees less hurricanes, making the Windward Islands an appealing option for an all year round Caribbean yacht charter.

St Vincent and the Grenadines makes a great base, offering east sailing plus access to St Lucia or Grenada. Sailo offers fantastic flexible options for either bareboat yacht charters, or for a more stress free experience, a captained choice enabling you to relax and fully enjoy your Carribean experience.

The Leeward Islands

The Leeward islands include the Virgin Islands, St Kitts and Nevis, Guadeloupe and Antigua and Barbuda. Experience colonial influences from the British, Dutch and French and plenty of local flavor added into the mix. Sailing the Leeward Islands offer countless smaller islands to explore and often perfect sailing conditions, making them a perfect yachting destination.

With a Sailo Caribbean catamaran charter in the Leeward Islands, you’ll be able to experience these stunning sailing vacations at your leisure.

For a cultural hit, Nelson’s Dockyard National Park is a restored marina and is one of Antigua’s top sightseeing attractions. In the remote southeast, Half Moon Bay is great for both snorkeling and body surfing in it’s calm waters.

Whatever your itinerary, Sailo has everything you need to help plan your tailor made, flexible Caribbean experience.

Our Favorite Sailing Itineraries in the Caribbean

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BVI Yacht Charters from Tortola

Starting Location

Start in Tortola to clear customs and pick up everything you might need for the next week sailing. This itinerary is popular and considered by many one of the best sailing holidays in the Caribbean that you can plan for!

Norman Island

• Previous stop Next stop

8 NM from last stop

Your first stop is the Norman Island. Sail around until you find the perfect spot to jump in the water and to cool off. Drop anchor and enjoy lunch at one of the restaurants on the beach. Most of our BVI yacht charters are equipped with snorkeling gear, perfect to explore the caves of this rocky island. Once you pick one of our Caribbean yacht charters, make sure to check with your boat representative what gear will be available on board for your trip.

Cooper Island

9 NM from last stop

Cooper Island is the next destination to test your snorkeling gear and capture unforgettable underwater memories for a lifetime. Sea turtles are also frequent visitors to these waters. Off the southwestern coast of the island is located one of the most popular diving spots in the BVI’s - the “Wreck Alley” - with four sunken ships transformed in amazing marine life habitats.

Salt Island

2 NM from last stop

Your snorkeling and scuba adventure on one of our BVI yacht charters continues at Salt Island. The most notable attraction is a big, complete wreck that you can explore underwater.

Trellis Bay

6 NM from last stop

Pull into Trellis Bay - home to popular full-moon parties and other exciting nightlife. Trellis Bay Market on the western side of the island is a good spot for fresh provisions. Go for a stroll to check the local art shops and stop for a drink or a nice lunch at the De Loose Mongoose. For a snorkeling afternoon trip, check out the northern side of the cay.

The Virgin Gorda Baths are an exquisite and unique natural formation. These huge rocks and the surrounding mini coves are great to explore above and underwater, or even climb. Moor your BVI catamaran charter (or yacht if that’s your choice) at the Devil’s Bay Fort Point and spend a great day in water. The nearby Devil's Bay local restaurant/bar is just a short walk away.

• Previous stop

10 NM from last stop

Your trip loops back around to the origin city of Tortola. Get reacquainted with dry land around the town before heading back home. We hope this itinerary will make one of your best sailing holidays in the Caribbean on one of Sailo’s BVI yacht charters!

Sailing the Virgin Islands

Starting Port

Come a few days early (or save time at the end of your trip) to visit the beautiful island of St. Thomas. Gather all your supplies for the next week of sailing on your USVI catamaran charter through the charming Virgin Islands.

Christmas Cove, Great St. James

6 NM from last port

The turquoise waters at Christmas Cove are perfect for an afternoon swim and snorkel post short sail from St. Thomas. The calm waters of this protected cove are a National Marine Sanctuary where you will see lots of fish, sea turtles, and friendly stingrays. This location is perfect for overnights on any of our Caribbean yacht charters.

Caneel Bay, St. Johns

4 NM from last port

Drop anchor on your USVI catamaran charter and visit the Caneel Bay Resort, which was built on the site of an 18th century sugar plantation. Bring our your inner "foodie" and visit the Beach Terrace for buffet-style offerings. Feel free to walk the grounds of this luxury beach resort while enjoying the sparkling lights of St. Thomas on the distant horizon, before heading back to your private yacht.

Jost Van Dyke

6.5 NM from last port

Jost Van Dyke is one of the finest among the Caribbean beaches with its lively bars, comfortable hammocks, and strangers that will be your best friend by the day's end! After a day spent on the beach sipping rum cocktails, Foxy's Tamarind Bar and Grill is a favorite of boating enthusiasts enjoying their time on Sailo’s BVI yacht charters. Enjoy their great local food, Friday and Saturday barbecues, flying fish sandwiches, grilled fresh fish, and lobster for dinner.

16 NM from last port

Green Cay is an exciting dive and snorkel site which has a series of pinnacles covered with brightly colored sponges and branching hydroid that shelter and abundant marine life. From the stunning coral beach you can walk to a small shipwreck of a more modern-looking boat. Before arriving on one of our BVI yacht charters at Marina Cay for the night, make one last stop at Sandy Cay, a picture-perfect little gem in the ocean, surrounded by white sandy beaches speckled with clusters of rock, green vegetation, and two lonely coconut palms. Tourists from all over the world come here on their Caribbean yacht charters to enjoy sunbathing, excellent snorkeling, and picnics with a view. Marina Cay, your stop for the night, is a flower-covered eight-acre island ringed by a powdery white sandy beach and sheltered by a lagoon with calm and warm waters. Enjoy a mellow night on the deck of your USVI catamaran charter with drinks and a dinner on board.

Spanish Town, Virgin Gorda

5 NM from last port

Moor your boat and explore the famous Baths, with the scenic boulders and the caves open to the sea. Enjoy the day snorkeling or diving the Wreck of the Rhone, famous from the movie "The Deep". Spanish Town is the perfect overnight stop for all sailing holidays in the Caribbean that include Virgin Gorda island, offering plenty of options for shopping and dining around the harbor.

North Sound, Virgin Gorda

Dog Islands are a small group of islets in the Sir Francis Drake Channel. They are part of BVI’s Marine National Park and Seabird Refuge making them great diving and snorkeling spots. After an activity-packed day, visit The Bitter End Yacht Club and dine at the Clubhouse Steak and Seafood Grille, a casual, yet elegant restaurant located right on the water.

20 NM from last port

On your way to Norman Island stop at Peter Island and explore one of the most beautiful beaches in the Caribbean: Deadman's Bay. It’s a great snorkeling spot and also a good option for a fresh lunch right on the beach. If you're looking for a quiet stretch of sand, take a walk to the secluded Honeymoon Beach at the tip of the peninsula. Once you drop anchor on one of Sailo’s BVI yacht charters at Norman Island (your overnight stop), try snorkeling around the 3 water-level caves at the base of cliffs. At the end of the day you can enjoy a casual dinner and a fun happy hour at the famous floating bar and restaurant Willie T’s.

St. Thomas, USVI

19 NM from last port

Your final destination is the delightful Frenchtown in St. Thomas. Boating enthusiasts sharing memories from their sailing holidays in the Caribbean recommend this small quaint town as home to some really great casual restaurants. Here you will make lots of friends as the bar is always filled with a crowd of very friendly folks. A perfect dining experience to conclude the perfect vacation on a Sailo USVI catamaran charter!

Island Hopping from Road Town, Tortola

Starting point

Choose one of Sailo’s Caribbean yacht charters in Tortola and set sail for fun and relaxed trip, hitting all the prime spots in the British Virgin Islands.

NORMAN ISLAND

8 NM from the last port

Start your adventure on one of our BVI yacht charters on Norman Island, an uninhabited rocky island, considered by some one of the hidden gems of the British Virgin Islands. Time to grab your snorkeling gear and explore the bountiful marine life or swim in the spectacular coastal caves.

COOPER ISLAND

Then you will visit the Virgin Gorda. Here there is opportunity both for Hiking and beach views. If you want to try both, you can hike along the boulders that end on a beautiful white sand beach.

VIRGIN GORDA

16 NM from the last port

A must on your to do list when sailing on one of our BVI yacht charters is a stop at Virgin Gorda. Go for a hike along the boulders or relax on the picture-perfect, white sand beach.

JOST VAN DYKE

20 NM from the last port

On your way to Jost Van Dyke make a stop to visit Guana Island - famous for the seven different white powdery beaches. Go snorkeling the reefs, relax in a hammock, or set up your own private picnic on land. And if you are in the mood for a walk, explore the tropical forest. Then set sail to the smallest of the four BV Islands - Jost Van Dyke - the perfect stop with an overnight to join the happy, laid-back crowd at the Soggy Dollar Bar or at Foxy’s. Drop anchor in White Bay and don’t miss your chance to try one of the signature rum cocktails at Foxy’s!

CANE GARDEN BAY

6 NM from the last port

Don’t miss your chance to stop and enjoy the Sandy Cay - a deserted island with a fantastic beach where you can relax and take in the breathtaking tropical view. Drop anchor and go for a swim or grab your snorkeling gear and explore the crystal clear Caribbean waters. After lunch, set sail to Cane Garden Bay on Tortola for your overnight anchorage.

15 NM from last port

Head back to Road Town Tortola for the end of your journey. We hope you had an amazing time on one of our BVI yacht charters and we hope to see you soon back on the water!

British Virgin Island - Sailing Holidays in the Caribbean

Get aboard on one of Sailo’s BVI yacht charters in Road Town and start your tropical nautical adventure!

Set sail to your next stop at Bight Bay (formerly known as Man of War Bay). This sheltered inlet is perfect for your first overnight. Explore Norman’s island water level caves and go snorkeling in the crystal blue water.

PETER ISLAND

3 NM from the last port

Your next stop - Peter Island - is famous for some of the best beaches in the British Virgin Islands. Drop anchor at Little Harbour: a quiet spot usually not so crowded. White Bay and Key Bay are the best anchorage spots on the south shore. Hop off and try the local Caribbean cuisine.

SALT ISLAND AND COOPER ISLAND

Spend the day exploring these two little charming islands. Salt is famous for the Wreck of the Rhone and the surrounding reefs - a spectacular snorkeling and diving spot. Cooper island has a protected anchorage, picture-perfect white sandy beaches and some of the best snorkeling sites in the BVIs (tip: try the crystal clear waters around Cistern point).

Your voyage on one of our Caribbean yacht charters must include a stop at the famous Baths. Indulge in the natural jacuzzis and go hiking the beachside boulders for an amazing view of the bay waters.

NORTH SOUND

2 NM from the last port

North Sound is a cluster of small islands off the northern tip of Virgin Gorda. Take advantage of the protected anchorage and the calm waters to try out watersports. A fun way to check the area is to glide the turquoise waters on a hobie cat! For a gourmand dinner with a fantastic view, make a reservation at the gorgeous and secluded Biras Creek resort (dress code required).

15 nm from last port

Head back to the home port carrying wonderful memories of your sail on one of BVI yacht charters from Sailo!

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A superyacht captain shares 3 things people who want to charter a luxury vessel should know

• Vacationing on a superyacht may sound like it's all Champagne and sunbathing.
• But before boarding a luxury vessel, superyacht captain Kelly Gordon advises keeping certain things in mind.
• Yachting is a summer pastime with risks and nuances for clients and crew.

Jeff Bezos and Lauren Sánchez soaking up the sun. Travis Barker and Kourtney Kardashian's wedding . Beyoncé's carefree jump into the ocean.

One of these images is likely what comes to mind when you hear the word "superyacht," a phrase generally used to describe a yacht over 80 feet in length.

While ultra-luxurious vessels are associated with all things carefree, tragic events such as the sinking of the Bayesian superyacht off the coast of Sicily on Monday is a reminder that yachting is a pastime with unique risks and nuances. It's unclear what the protocols were on the Bayesian.

For those keen on the idea of chartering a superyacht, captain Kelly Gordon, 42, told Business Insider there are a number of important factors to consider before hopping on board.

Gordon fell in love with yachting after she stepped aboard a yacht for the first time in her mid-20s.

Hellbent on reaching captain level, Gordon quickly worked her way up the chain of command. She's spent most of her time sailing the Bahamas and the Caribbean and is now based in Florida, where she works as a captain on a 108-foot-long privately owned vessel.

Gordon, who has over 12,600 followers on Instagram , shares three factors to keep in mind before boarding a chartered superyacht.

Think of the process of chartering a superyacht as buying a house

One of the most important things to do when chartering a superyacht is to work with a charter broker, Gordon says.

"The charter manager's job is to No. 1: find you a safe boat," Gordon said, adding that in her experience, "Not all programs put safety as high up on the list as it should be."

She also likes to equate charter brokers to Realtors in that they take on the role of finding you the best option for your taste.

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"You find one that you gel with really well and has a good reputation, and then you discuss with them what your budget is, where you want to go, what your activity levels are, what your personalities are like," Gordon said.

Pairing clients with a crew that aligns with their characteristics is a huge part of a charter broker's job, Gordon said.

"If you think about it, you're living with that crew for 24/7, around the clock," she said. "You're not going put someone that just wants to sit and read books all day with a crew that's extremely active."

Find a crew that is competent and prioritizes safety

Charter brokers also help match clients with a competent crew that prioritizes safety.

"I don't know that many people realize just how much their life is in our hands when we cast those lines and we go to sea," Gordon said.

Part of that is having a safety briefing, which Gordon carries out every time she welcomes clients onto a chartered vessel before leaving a dock.

A thorough safety briefing includes informing clients about the location of safety equipment and lifejackets and the procedures for events such as a fire, a person falling overboard, or the boat sinking.

"You should have a safety briefing, and if you don't get one, you should ask for one," Gordon said.

The process, she added, can be different on privately owned yachts, where passengers may be familiar with the vessel.

The Bayesian is a private yacht owned by tech tycoon Mike Lynch; it's not yet known what kind of safety protocols staff and guests were trained on.

Make sure there's a member of the crew on watch 24/7

"A lot of charter guests think when they go to sleep, the crew goes to sleep," Gordon said.

But that shouldn't be the case, she added. "You want to be on a boat knowing that someone's up, because if the weather changes or the anchor starts to drag, you need somebody that's up and ready to go and get everybody else to handle it."

Among the biggest weather risks are tornados, which can be extremely difficult to predict and prepare for whether you're on land or at sea.

"I'm from the Midwest, where tornados pop up," Gordon said. "It's hard to see a tornado coming, and if you do see it coming, the tornado goes where it wants to go."

Most often, that leaves people near the weather event with just minutes to ready themselves, which is even trickier "in the middle of the night."

While rapid changes in weather are tough to contend with, Gordon recommends researching the areas you are sailing in beforehand, like you would when visiting a new country.

"It's no different than if you're going on vacation on land," she said. "You want to know where you're going. Don't put that just all on the crew."

While the research doesn't have to be as extensive as the crew should be doing, it's important to still be "responsible for your own self as well as your family and your guests."

Watch: Why it costs $1 million a day to run one of the world's biggest cruise ships

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The Caribbean’s Hot One-Design Fleet

• By Dave Reed
• August 13, 2024

I’d love to look around and enjoy the scenery, but I can’t take my eyes off the leeward bow that’s slicing through the Caribbean at 20 knots. I’d been advised earlier: The fine line between full-tilt and pitchpole is somewhere right around the chine on the wave-piercing bow. The warning also came with a caveat: “The faster we go, the safer we go.”

That’s the wisdom of Pierre Altiere, a master of the Diam 24 trimaran, with whom I’ve scored a ride for the St. Maarten Heineken Regatta. The point of the exercise is to experience firsthand the hottest one-design fleet in the Caribbean. Altiere’s boat is named Cry Baby , which I may eventually come to understand, but right here, right now, all I can think about is the gust breathing down my neck.

I ease the gennaker sheet in my hand and watch the bow submerge. Oh, sh-t, I think. Here we go. I’ve seen pictures of Diams tumbleweeding, but the bow porpoises. A ball of seawater smacks the forward beam and explodes into a cloud of sunlight sparkles and foam.

With a jab of the tiller bar, Altiere redirects the boat and reloads the sails. The daggerboard hums a few octaves higher as we skim across the shallow blue flats of Phillipsburg Bay. It’s thrilling and a little terrifying, and thankfully, we’re just getting started.

It’s an early March morning on St. Maarten’s Kim Sha Beach, on the bustling Dutch coast where six identical 24-foot trimarans sit under palm trees, surrounded by umbrellas, chaise lounges and rental kayaks. Four other Diams swing on their anchors a doggie-paddle’s distance from the beach. This is the homegrown Diam 24 One Design fleet, which in a few short years has multiplied from three to 10. Soon enough, Altiere promises, if his Diam dream scheme pans out, we will be looking at as many as 20.

Altiere, I’m told, is the spark, the one who started it all, and judging by the parade of sailors seeking him out for advice, parts, assistance and you name it, it’s obvious that not much happens without Altiere. As we rig our own boat, interrupted by phone calls and favors, he gives me a quick lowdown on the Diam, which was created by Vianney Ancelin, a French multihull sailor and boatbuilder. Ancelin’s vision was a recreational multihull that average sailors could handle—sporty but not lethal, high-tech but not overpriced. That was the idea before the Tour de France a Voile—a multistage regatta—adopted the Diam as its official one-design. Pro race teams with million-dollar budgets promptly priced amateurs out the class, and then the pandemic put a fork in the Tour. The builder, ADH Inotec, stopped production at just north of 100 boats. With the Tour on hold, however, there was suddenly a pile of secondhand race-ready boats, many with containers full of unused spares, most fetching $20,000 to $30,000.

Enter Altiere, the tall, jovial and hard-charging Frenchman who taught at a sailing school as a young man and then opened his own in Tahiti before landing in St. Maarten, where he operates a thriving private catamaran charter business. As a top-level F18 catamaran sailor not far back in the day, a friend once invited him to race a Diam in France. He knew little to nothing about the boat at the time. “As an F18 sailor, I knew what I was doing,” he says. “I hadn’t raced [in Brittany] in 20 years, but we somehow made it onto the podium, everyone applauded us, and I enjoyed it so much that the next day we started talking about becoming an agent for North America.”

He did, but the big continent was impossible to crack, so he pivoted to a better plan: bring potential buyers to the boat and give them a taste. Step 1: Establish a Diam base at home in St. Maarten and show off the boats. Step 2: Enter them into the region’s big-draw regattas: the Heineken and Les Voiles de St. Barth.

“There’s nothing better than an easy flight to St. Maarten, throwing your bag in the hotel, and jumping onto a Diam that same day,” Altiere says. “Just like me, I was offered a chance, I had a great experience, and right after that, I bought a boat. That’s the easy-regatta concept here: Fly in, race, celebrate, fly out.”

And that’s how “sort-of” New Yorker Adam Holmes and his buddies Ben Ferraro and Bob Young were lured to Kim Sha in late March for the Heineken Regatta. Holmes, an advertising executive and Long Island-based racing sailor, had heard about the Diam fleet through a friend in St. Maarten, who connected him with Altiere, who had one charter boat available for the Heineken Regatta.

How much for a good time?

Five-grand—tops—according to Holmes’ mental math, and that was with a top-shelf condo, on the water, for a week. Altiere’s charter fee, which included four days of racing and two days of practice, was only $3,700—worth every penny on the speed-to-dollar scale. For months, the three of them exchanged Diam sailing videos that they found online. “That was like the start of the adrenaline rush,” Young says, and when they jumped on board for their first figure-it-out-yourself session in St. Maarten, the real thing was a real rush.

“We didn’t get a very detailed briefing before our first sail,” Holmes says. “At one point on the first practice day, we were sending it at like 19 knots, and the hull was so far underwater. Bob had the kite strapped in hard and we were just flying…like really, really on the edge. The Diam guys following us in the RIB and yelling at us in French were freaking out because we hadn’t yet signed any paperwork.”

“At the time,” Ferraro adds with a laugh, “we had no idea we were on the edge—we didn’t know any better.”

But with a few more hours of practice and less than 30 minutes of one-on-one with Altiere, they were ready enough to throw themselves straight into the races. Ferraro was nominated to drive, Holmes got the back-breaking main trimmer’s spot, and Young took on the busy end at the front of the cockpit. 

On the first morning, the breeze is up to 15 knots, and even though the start is in 90 minutes, the vibe on Kim Sha is bizarrely relaxed. Beach attendants rake the sand for the inbound tourists while sailors wander about in farmer-john wetsuits, surf trunks and rash guards, most of them conversing in fast-paced French and tinkering with their boats.

Among them is Erick Clement, one of the originals. He is a master of the Caribbean multihull racing scene and enjoying his retirement from F18 catamaran racing. Daily yoga, and healthy eating keep him young and in Diam-worthy shape.

“The speed is good and the boat is not complicated, but you have to get a feeling for it,” he tells me in his best broken English. “When everything is right, the steering is balanced perfectly, and you listen for the noise of the daggerboard—that helps you know when it is right.”

As a simple three-crew boat, the roles are straightforward. Whoever has the pleasure of helm also gets the traveler—the capsize preventer. The middle crew manhandles the insanely loaded mainsheet, trims the gennaker, and assists with dousing it. The forward crew is responsible for the self-tacking jib sheet, sail controls (outhaul, cunningham, mast rotator), gennaker hoisting and the daggerboard. Between calling tactics and jibing angles, housekeeping the trampoline, and watching for traffic, it’s an active boat for all involved, especially when big-breeze buoy racing in St. Maarten.

“All crew are super-important,” Clement adds. “If one is not playing the game, you can’t do anything. You have to have a good balance with each other.”

That will be a problem for us on Altiere’s Cry Baby because we are rotating new teammates every day. With us for the first day is a strapping young Frenchman named Corentin, who goes by Coco. He’s one of Altiere’s charter boat captains and has some Diam racing experience, which is good because we’re straight into the first start without a lick of practice. It’s a chaotic five minutes of weaving through rush-hour traffic: big custom raceboats, cruisers, bareboats and two 100-footers, all pinging the starting line.

The Diam will go from zero to 15 rapidly, but it’s not the kind of boat you can luff-and-hover on the start. Full speed is Altiere’s preferred approach, and with 45 seconds remaining in the opening sequence, he is stalking next to the committee boat, mentally calculating the layline and time to kill. But the other boats are stacking up at the starboard end, making what looks to be an impossible entry. But, hey, Altiere is the man and the defending champ. This is his domain. Who am I to doubt?

At 30 seconds, he booms, “OK. We go!”

And go we do, bearing away to full hum, straight toward the big catamaran committee boat. Just when it looks like he is going to pull off a high-speed barging start, Holmes and his crew tack in front of us and stuff the boat into irons—three sun-creamed deer in our headlights.

It’s either them or the committee boat, but Altiere pulls the hand break, and we coast to a near stop. The bow of our center hull disappears beneath the catamaran’s bridge deck, and the starboard bow just clears the cat’s starboard transom. I run forward and push off, and Altiere apologizes while cursing the New Yorkers for their erratic driving.

“I mean…it was our first race, and we were still trying to figure out how to tack the damn thing,” Young says. “That was a little nutty.”

“OK, let’s go,” Altiere shouts once again. More trim!” And with that, we’re chasing down the fleet. I pull the mainsheet as hard as I humanly can. The sail is board-flat and the telltales are streaming.

“More trim!” he shouts again. “We do it together.”

He reaches forward with his big right arm, grabs hold of the sheet with one hand, and together we grunt another 2 feet. The weather hull rises higher, and then the center hull breaks the surface. I’m staring at the line that Altiere had drawn on the bow with a Sharpie. That’s my fine-line guide for the week.

“More speed,” he says. “We will get them.”

I pull but get only another inch. He reaches in and gets another 6, finds his gear, and lets it rip.

The collective opinion on Kim Sha is that Altiere is the best sailor in the fleet, and I can see why. He effortlessly threads the trimaran around oncoming traffic, across big waves, and through giant puffs that pin other boats on their ear. He will dive to leeward of another boat and sail right through its lee. Downwind, he sits inside the center hull, hunched, with his hand behind him on the tiller bar, laser-focused. He senses every subtlety of the boat and knows what it will do before it does it. And more than once, when we sail into a lull and our speed drops, he puts his hand up in the air and says, “Bwaah…come on, wind, what is wrong with you?”

He’s seriously annoyed with the breeze for denying him his speed.

The first race is a windward/leeward blur, and we somehow manage a midfleet finish. Same for the others that follow, but our mishaps reflect our thrown-togetherness. We’re fast in a straight line thanks to Altiere’s skills, but every slip-up is a dozen boatlengths lost—and that’s no lie.

Back on Kim Sha, there’s a beach bar 10 feet from the boats. It’s got reggae, cold beer and cheeseburgers in paradise. The fellas from New York are happy to be back on the beach with their recovery juices in hand.

“That was kind of devastating,” Ferraro says. “We were miles behind on all the races, like it was not even close. We weren’t going to drink, but then all of sudden, we’re standing there with a drink in our hand and were like, ‘What just happened?’”

Young isn’t bothered at all about the results. He’s whipped, but it’s worth it: “All I remember was thinking, I’ve never gone that fast on a sailboat. I think our top speed was 20.7. The sound of the boat and that hum going at that speed was just like, holy sh-t. Let’s just hold on.”

With the wind forecast to peak into the mid-20s, the St. Maarten Heineken Regatta’s legendary around-the-island race is next on the to-do list. Big island, big breeze and it’ll be big-time fun, Altiere promises me when we meet at the beach and introduces me to Camille, another of his charter boat captains. She’s petite, and Altiere confesses he had miscalculated the wind forecast when lining up crew for the regatta.

“We will struggle a bit upwind because weight is very important,” he says, slapping a big hand on my shoulder and cracking a big smile. “But we will be very, very fast on the reaches.”

And he isn’t kidding.

To start our circumnavigation, the race committee dispatches us on a short upwind leg. Once we turn downwind and deploy the gennaker, we’ve got many miles of open-ocean high-speed tropical send. In these conditions, Altiere is in his element and sails right up to and past boats that got ahead of us on the upwind leg. Our top speed, according to my watch, is 22.9.

But every downhill has uphill, and way too soon we’re furling the gennaker, lashing it to the trampoline, rounding an orange tetrahedron, and pointing three bows into steep, wind-whipped waves.

“More trim!” is all I hear for the next hour, or “More speed!”

Each time, I pull with everything I’ve got, the rope shredding the palms of my cheap gloves. With only the leeward bow in the water, Cry Baby kisses wavetops, making this upwind slugfest that much more enjoyable as we short-tack the island’s coastline. After one final tack to port at the top of the island, Altiere gives us the command we’ve been waiting for: “Go gennaker, now!”

The moment that sucker fills, the daggerboard is singing, water is exploding through holes in the trampoline mesh, and we’re cruising at 20 knots. Altiere carves up and down following seas and reels in the boat to leeward of us as if it’s dragging a drogue. The three of us are pinned to the aft beam, weight back as far as it can possibly go. There will be no pitchpoling today. Lush green island to starboard, sparkling blue sea all the way to the finish. It’s heart-racing tropical sailing the likes of which I’ve never experienced.

Later, as I shuffle to a hotel shower, I get a pop-up alert on my Garmin watch that I’ve never seen before: “Recovery Time Delayed. A high level of activity today slowed your recovery.”

As if I need reminding.

The New Yorkers had a heck of time getting around, unaware of water pouring into an unsealed cockpit hatch, enough to have their Torquedo floating inside the hull. “We were hanging with everyone until we got to the top of the island,” Ferraro says. “But once we got around the top of the island, everyone just peeled away from us. We had no idea why.”

Hundreds of pounds of water sloshing around the center hull will do that to you.

Regatta organizers serve up a feast for the next day, with a full menu that includes a 20-mile distance race to Marigot Bay on the French side of the island, a windward-leeward race in the bay, and a return distance race. Our new crew for the day is 13-year-old local Optimist champ Sarah Micheaux, tiny and timid, but seemingly game for her first Diam outing. She speaks only French, so Altiere explains the ropes.

Before we even strike the line on a high-speed gennaker reaching start, Micheaux is shivering, puking, and white-knuckling Altiere’s leg. While redlining at 20 knots, he pats her on the back like a tender father, assuring her that all is well.

We round the reach mark with Micheaux out of commission, so he hands the tiller to me so he can go forward and rotate the mast by hand. It’s my first go at driving, and my tendency is to drive it like a monohull—oversteering through waves and feathering through the big gusts. Altiere corrects me and keeps goading me: “More speed. Even more speed. Good.”

All I have to do is bear away a few degrees, get the center hull unstuck, and the boat levitates with only the leeward bow punching through the waves.

“See?” he says. “Speed. Always more speed.”

After the ensuing and harried one-lap windward-leeward race in the bay, we’re lining up for the 12-mile return sprint, which is another shot-out-of-a-cannon gennaker start. Thankfully, this race has zero upwind sailing. This one’s a reach-fest, and this is why we reach through life.

“The sail back from Marigot was just epic,” Holmes says. “Just screaming. Unbelievably fun. We were finally starting to get a handle on the boat.”

On the fourth and final day, we’re back to buoy racing, and while there’s more tears than cheers on Cry Baby , the sort-of New Yorkers are feeling their mojo.

“We were in the mix,” Holmes says. “We had good starts, and we were with the group upwind. There are some cool photos of us kind of like leading the bulk of the fleet around the course—at least that’s what it looks like.”

Ferraro agrees that they were sharp upwind, “but downwind, we just couldn’t find the low and fast mode. We couldn’t figure that out.”

That’ll be next year’s challenge.

 “I’m looking into buying one,” Holmes says, weeks later, back in the office and scheming with Young to go in on it with him. “It’s easy to get to St. Maarten, and from what I’ve seen, they have these cool regattas and beach parties, the sailing is amazing, and it all looks like so much fun. I think about that boat every day, so I definitely have to get back on it.”

Ferraro is hooked as well. “I can honestly say that after all the stuff that went on during the week, good and bad and stuff like that, even with all the chaos and stuff. That was still the most fun sailing I’ve had in a really long time.”

When, and if, they do get their hands on a Diam, there’s only one place they plan on putting it. “If you’re going to do it right, you gotta keep it in St. Maarten,” Young says.

And that’s how Altiere and his St. Maarten crew will get to 20 boats soon enough. If space on Kim Sha becomes an issue, no problem, he says. There are plenty of beaches on St. Maarten to spread the fun around.

“We’ll figure it out,” Altiere says. “I know we can make this work. The dream is real, and there is room for this kind of full-service experience. It’s a gateway to a sailing vacation.”

Sold. More speed coming my way.

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If you don’t want to stay landbound on your next holiday, these luxe properties offer the ultimate amenity

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Mayakoba, Mexico 

Set along Mexico’s Riviera Maya, Mayakoba is a gated 595-acre enclave, home to four hotels— Banyan Tree Mayakoba , Rosewood Mayakoba , Andaz Mayakoba , and Fairmont Mayakoba —each with access to private yacht charters on Mayakoba’s Van Dutch Yacht . The 55-foot vessel, kitted out with Hermes leather seats, two bedrooms, and a full kitchen and bathroom, can accommodate up to eight guests for a range of bespoke excursions. And en route to destinations like Cozumel or Playa del Carmen, sunseekers can take advantage of activities like scuba diving, jet skiing, and gliding through the Caribbean with an underwater scooter. (From $3,100 to $11,000, changing seasonally, for four- to eight-hour excursions)  

Borgo San Pietro, Italy 

The Mark Hotel, New York City 

In the heart of the Upper East Side, not far from Central Park’s famed Conservatory Water pond dotted with toy sailboats, The Mark Hotel is home to plush, Art Deco-inspired rooms, elegant restaurants, and access to a sailboat of its own. Guests embark from Tribeca’s North Cove Marina for a two-hour private charter aboard the 70-foot Herreshoff sailboat, which can accommodate up to 25 for cocktails, a custom menu from one of the property’s restaurants (including Caviar Kaspia or the eponymous fine dining spot helmed by Chef Jean-Georges Vongerichten) and spectacular views of the Statue of Liberty. (From $7,000 for a private excursion)

Six Senses Ibiza, Spain

Ibiza may be best known for its thrumming nightlife, but those after a little tranquility may find it at sea. On the hills overlooking the Balearic, Six Senses Ibiza offers access to such calm aboard one of several vessels in its portfolio, including a Monohull sailing yacht, a Scanner Envy 950, and a Solar Catamaran, powered by solar panels. A full- or half-day trip launches from Xarraca Bay to explore secluded coves and secret beaches where those-in-the-know go for a perfect combination of relaxation and stunning scenery. (From about $950)

Shangri-La London, England

The Charleston Place, South Carolina

With plenty of picturesque coastline to explore, it’s not hard to find a vessel to take you out on the water in Charleston. But in the charming South Carolina city, you’ll only find one Hinckley EP Picnic Boat available for charter. At The Charleston Place , guests of the elegant boutique property can board Moonrise , crafted by the iconic American shipbuilder, for a private sunset tour, or to spend the day off the coast of one of the city’s beautiful barrier islands. (From $1,100 for a two-hour excursion for up to six guests)

Burj Al Arab Jumeirah, Dubai 

Towering over 1,000 feet, Burj Al Arab Jumeira has been a sailboat-inspired jewel on Dubai’s Arabian Gulf for 25 years. And now, thanks to a recently-launched partnership with Beno Luxury YachtRental , guests can add a sailing experience to their stay, too. Among the fleet of four yachts on offer, the 115-foot Santorini Superyacht can accommodate up to 80 guests for a  two-, three-, or four-hour jaunt that can include a butler, DJ, and custom catering from the property. (From $4,083 per hour)

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Breaking news, i lived ‘below deck’ on a luxury yacht — here’s what you need to know.

Tahiti, St. Thomas and the French Riviera — I’ve yachted in all of these exotic locales, albeit from the comfort of my couch. And, millions of Americans are in the same boat.

In 2013, “Below Deck,” introduced the masses to the most glamorous mode of traveling: yachting. Since then, it’s become a Bravo mainstay with Season 9 of “Below Deck Mediterranean’’ premiering in June.

But how real is the reality show? I spent five nights on a yacht in Croatia to find out.

A tip on tipping

My suitcase wasn’t bursting with Benjamins. An agency at your final destination provides cash for the crew’s tip money. While you’re expected to tip $30,000 for a two-night cruise on “Below Deck,” in real life you only have to tip 10% to 15% of your charter fee. That’s about $10,000 for a two-night cruise on a 180-foot charter yacht like Mustique (from $250,000 a week), which stars in the new season.

According to Zvonimir Androić, president of the yacht charter company Via Croatia, more often than not, the tip comes from what’s left over after provisioning.

So, shun the Dom Pérignon and skip the beluga caviar, and you’ll have money to spare.

What’s up, dock?

In real life, “Below Deck’s” favorite commercial-break cliff-hanger isn’t nearly as dramatic. Docking in our yacht, Via Croatia’s five-cabin, 100-foot Adriatic Escape (from $52,800 a week), was breezy.

I asked the crew if they hated setting up the slide — a tortuous, Herculean task if you believe what you see on TV.

“It’s not that bad,” a twentysomething Croatian deckhand, as cute as his on-screen counterparts, told me. “That said, we’re definitely not sad if you don’t ask for it.”

Play it cool

Despite being served meat on more than one occasion, my vegetarian co-guests on board weren’t divas when it came to cuisine — a major source of chef-related stress on the show.

Tantrums aren’t the norm Barbie Pascual, the “Below Deck” stewardess famous for putting up with former “RHONY” star Jill Zarin’s demands for the perfect Diet Coke in the “Real Housewives of Grenada” episode, tells me. “Guests know they are being filmed so their reactions are more extreme than they’d be if the cameras weren’t around,” she says.

Pascual’s biggest tip for first-time yachters? Don’t go skinny dipping, like they do on the show, after dark.

“People forget about currents, sharks, etc.,” she says. “Jumping in the water should always be with the captain’s consent!”

Our humorless Croatian yacht captain was a far cry from “Below Deck Mediterranean’s” affable Captain Sandy Yawn. I think we only saw him twice over the course of four days, and he definitely didn’t join us for dinner.

That was fine by us because the stews and deckhands were always handy with anything we needed — including at chat.

Asking for it

“No” is a word you’ll never hear on a yacht, unless there is a safety issue, Pascual says.

While we didn’t ask our crew to do a striptease or decorate for ‘70s night (two recurring requests on the show), out-there demands aren’t out of the question, as long as you’re willing to pay for it.

For example, Via Croatia is currently retrofitting one of its multimillion-dollar superyachts for an upcoming charter booked by a multigenerational Jewish family from Florida.

“In addition to paying the charter fee, the client is literally buying everything new: pots, pans, silverware, et cetera,” said Androić. “They’re even spending $30,000 on a new tender for the elderly mother-in-law.”

Now, I’m no reality show producer, but a picky primary trying to keep his wife, her elderly mom and their kosher kids happy at sea has the makings of an Emmy Award-winning episode.

Yachting on a budget

Charters are cheapest at the beginning and end of a destination’s season. Via Croatia’s yuppiest yacht, the 160-foot, 12-cabin Agape Rose , fetches $200,000 a week in July and August. But it’s just $164,000 a week in April and October. Divide that by 24 of your closest friends and family and it’s just $6,800 a person.

If that’s still too much, consider booking a yacht club suite on one of MSC Cruises ’ Mediterranean voyages.

Sure, you’ll be on a cruise liner, but for $1,659 a person you’ll be treated to seven nights of private butler service with a private pool and restaurant that the pleb passengers don’t even know exists.

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Choosing Your Offshore Escape Vessel

By: John Neal, mahina.com Sailboats

The dream of buying a boat and sailing to exotic islands is a powerful and exciting one and an important part of achieving that dream is selecting the right boat to take you over the horizon in safety and comfort. Here’s how to successfully go about it.

It’s All About Sailing

First, ensure that you enjoy sailing and living on a boat, and unless you plan on single handing, that your partner does as well. If you’re new to sailing, sailing and navigation lessons are an excellent starting point. Try a 7–10-day ASA live aboard cruising/learning experience. Even better, consider a course in an area you’re interested in eventually cruising on your own. If the Caribbean is one of your dream cruising destinations there are several ASA liveaboard programs in the British Virgin Islands which is hard to beat as a fun venue for gaining skills and experience. 

Educate Yourself

Read boat reviews, scan owner’s group websites for troublesome problems specific to certain makes or models, read about yacht design and safety. Go sailing on as many different types of vessels as possible and consider crewing on local races. Take courses on navigation, offshore passage making, marine weather, sail repair and diesel engine maintenance. If your cruising plans include ocean crossings, consider signing up for a sail-training passage where you’ll be standing watch and learning 24/7. The more time and energy you put into obtaining skills important to cruising, the better yacht selection choice you’re likely to make and the more self-sufficient you’ll likely be.

Be Realistic

Many people searching for their dream boat have unrealistic expectations or get fixated on specific design issues. If your plans are for serious offshore cruising, ensure that safety and seaworthiness rate higher on your priority list than in-port comfort and interior volume. Compromise is important when selecting any boat. Chances are you will not find any boat in your price range that exactly meets all your criteria, so be prepared to be flexible.

You should plan to purchase your boat at least 1 – 2 years before departure bearing in mind that it may take 6-12 months of serious shopping to find a boat that meets your criteria. If the boat you purchase is over 15 years old and in need of some work it can easily take 6-12 months or longer to get it offshore-ready. You’ll also want to allow time to become familiar with sailing your boat and getting accustomed to living aboard.

Planning on cruising as a couple? Then each of you must be prepared to singlehand your boat, being conscious of your abilities and limitations. Seasickness or illness may incapacitate either of you, leaving the other person to handle everything. Safety dictates a boat with manageable sails, a dependable windvane selfsteering system and a powerful, dependable autopilot. 

If you’re planning on purchasing a boat over 42’ and aren’t as strong as you used to be, consider increasing your level of fitness and the option of selecting a boat with or adding a furling mainsail, bow thruster and possibly electric winches. This equipment adds cost, maintenance, weight and complexity but being able to easily handle your boat is important and adds to the enjoyment of cruising.

Go Newer and Smaller

To purchase a newer yacht that isn’t going to need an expensive, time-consuming refit, you may need to downsize your ideal size requirements. If this means purchasing a 12-year-old 38’ boat instead of a 20-30-year-old 45’-50’ boat, you will be far ahead; having more time to cruise and reducing your overall cost of ownership. Also, maintenance, insurance and moorage costs go up exponentially with the length of boat.

Boat Age vs Your Age

The older you are, the newer the boat you purchase should be. If you’re in your 20’s, you’ll likely feel like you have more time and energy than money. You’ll have the energy and motivation to work hard on a bare bones boat and then be keen to set sail, with or without a lot of gear that older people frequently deem necessary. If you are over 60 and inexperienced, you should consider a boat less than ten years old. 

Age of Boat vs Time and Cost of Ownership

The older your boat is, the more time and money it will take to go cruising.

On a boat 20+ years old, you can easily spend an additional 50% to 100% of the purchase price replacing rigging, sails, tanks, engine, and electronics and upgrading the electrical system. This refitting process frequently takes one to two years. With a boat that is new or less than ten years old much of the refit time and cost and is saved. 

Another good option is to purchase an older boat that has recently been refit by the seller and is ready to go. It will likely cost slightly more than comparable boats of the same age but will cost far less than outfitting an older boat that has only coastal equipment aboard. 

Finding Your Boat

Websites like YachtWorld.com are invaluable as they cover most of the world. Bargain basement boats priced under $30,000 are easier to find on For Sale By Owner (FSBO) sites. If you’re within six months of purchasing and have your financing in order, you may consider using a buyer’s broker. They should have connections to potential boats that you may not be aware of and save you time by cutting through the “broker babble”.

Market Trends

Currently it’s a seller’s market in North America, with the very limited inventory of quality, offshore-capable boats in the under $100,000 and under $200,000. European prices and inventory are currently substantially better than North America. Catamarans are the hottest category, particularly in North America.

Distress Sales

You may come across vessels that have recently had substantial and expensive upgrades completed yet haven’t cruised anywhere. Often these boats are the result of people who, during the refit and preparation process, have had health or financial hurdles arise or become too exhausted to go cruising. If the sellers have selected quality equipment and undergone an intelligent refit, these distress sales can represent excellent savings of time and money. It’s still imperative to get the right boat for your plans as a great deal on the wrong boat is still the wrong boat. 

Where to Purchase

It is wise to spend considerable time researching and deciding where you most want to cruise and just as importantly, where will be an easy place to purchase and outfit a vessel. Insurance agents and underwriters frequently recommend that you charter in your destined cruising grounds first, at the same time research the selection and prices of boats available, boat yards and outfitting services.

If you’re interested in cruising specific areas before planning long passages, purchasing a boat on location may be a good choice.

• This article is taken from a free 65-page e-book, Selecting and Purchasing an Ocean Cruising Sailboat , by John Neal.
• Download a free list of 158 builders & 424 models of offshore capable cruising boats .
• Boat Selection Consultation & Mentoring Service from mahina.com

LIVE SEMINAR ● OCTOBER 12 ● ANNAPOLIS, MD

Join seasoned sailor and boat-buying aficionado John Neal during the 2024 Annapolis Sailboat Show for an insightful, information-packed live seminar. Gain a comprehensive understanding of the current boat market, the overall purchase process, and essential insurance requirements.

About The Author

Since 1976 John Neal professionally consulted with over 10,000 sailors seeking cruising boats. His experience in the marine industry is unique; 408,000 offshore miles and 50 years worldwide ocean sailing experience plus boatbuilding, surveying and previously owning a yacht brokerage.

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Live updates: Seven dead in 56m superyacht Bayesian sinking tragedy

Seven people have died in the Bayesian sinking disaster. These include the six missing people who were inside the yacht when it sank, as well as a seventh person who was located shortly after the disaster. The seventh person is understood to be the yacht's chef, Recaldo Thomas. The other six are:

• British tech entrepreneur Mike Lynch, once dubbed 'Britain's Bill Gates'
• Lynch's 18-year-old daughter, Hannah
• Morgan Stanley's chairman, Jonathan Bloomer
• Judy Bloomer, wife of Morgan Stanley chairman
• Chris Morvillo, a lawyer working for London-based law firm Clifford Chance
• Neda Morvillo, an American jewellery designer and Chris' wife

It is understood that the yacht was being used to celebrate Lynch's recent victory in a 13-year £8 billion fraud acquittal.

No one remembers the mast snapping before 56m superyacht Bayesian sunk, says crew

No one recalls seeing the mast snap on board the 56-metre Perini Navi sailing yacht Bayesian which sank off the Italian island of Sicily on 19 August. The eyewitness account of a crewmember on board the vessel, which was obtained by BOAT International , said that the boat was struck by a freak weather event which led to the yacht heeling at around 20 degrees to starboard. As crewmembers were securing items, the heeling angle began to increase rapidly until the yacht started taking on water and sank rapidly.

The crewmembers who were up on deck were able to evacuate the yacht with minor injuries. The yacht is understood to have sunk in just twelve minutes, and it is believed that a "major ingress" of water from the top down would have caused the sinking, according to a captain who wishes to remain anonymous. This is based on the fact that no breaches have been reported in the yacht's hull, and the fact that the yacht should have been able to remain afloat with two flooded compartments.

"Very difficult to understand what could have overwhelmed a vessel of that size" says captain of sistership

The captain of the sistership to the sunken 56-metre Perini Navi sailing yacht Bayesian has said it is "very difficult to understand what could have overwhelmed a vessel of that size" and called the 56-metre Perini Navi series "bulletproof".

David Hutchinson, captain of Rosehearty , said he had taken the yacht around the world multiple times and he had "total faith in the boat".  "We've been to Antarctica and Chile, and we've had her in 70 knots of wind," he says, and the vessel had never put them in a situation that felt unmanageable.

However, Hutchinson noted there were differences between Bayesian and Rosehearty ; notably, Bayesian's  74-metre mast, which would have been heavier and added increased windage. The yacht's layout was also different, with guest accommodation on Bayesian located further forward.

Live updates

• During a news conference on Saturday morning (24 August), prosecutors confirmed they are in the early stages of investigating a "crime hypothesis" of culpable shipwreck and manslaughter. Authorities also said the yacht likely sunk because of a downburst (powerful wind that descends from a thunderstorm), rather than a waterspout.
• A search and rescue for six missing people has concluded. The final missing person is understood to be Hannah Lynch. 
• According to Reuters, six bodies have now been found in the sunken yacht. These include Mike Lynch, a British technology entrepreneur who co-founded Autonomy Corporation and founded Invoke Capital, although Italian authorities have not confirmed this.  
• One person was found immediately after the yacht sunk, and this is understood to be the yacht's chef. 
• Lynch’s wife, Angela Bacares, and a one-year-old are among the fifteen people rescued along with Bayesian' s captain, James Cutfield.
• Another sailing vessel in the area, the 42-metre Sir Robert Baden Powell ,  stepped in to offer assistance in the initial rescue.
• Divers have been able to reach Bayesian' s sunken hull, which lies at 45 metres of depth about half a mile from the coast. The yacht had the largest aluminium masts of any sailing yacht on the water.
• Eyewitnesses in the area reported "hurricane" conditions off the coast but local weather websites did not indicate any severe squall, which suggests that the weather event was not forecast.
• At around 5am local time on 19 August, Bayesian was hit by bad weather and sunk.  The sailing yacht was anchored or idle at the time of the incident.

Built in Italy by renowned builder Perini Navi and delivered in 2008, the yacht's naval architecture was developed by Ron Holland Design while the interior design is by Rémi Tessier . She was formerly known as Salute and was last refitted in 2016. She was listed for sale earlier this year, according to BOATPro . The yacht had accommodation for nine guests and 12 crew.

BOAT International will update the story as it develops.

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