caribbean sailing yacht charter

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798  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.

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Explore the Caribbean

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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 $1,094,000 p/week ♦︎

115m Lurssen

115m   2021

from $2,874,000 p/w eek ♦︎

Black Pearl 14

105m Oceanco

105m   2018

Christina O 34

99m Canadian Vickers

99m   1943/2020

from $774,000 p/w eek ♦︎

Carinthia VII 12

97m Lurssen

97m   2002/2023

from $1,547,000 p/w eek ♦︎

97m Feadship

97m   2017/2022

from $1,775,000 p/w eek ♦︎

CC-Summer 12

95m Lurssen

from $1,769,000 p/w eek ♦︎

from $1,327,000 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 $1,094,000 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

from $1,334,000 p/w eek ♦︎

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 $939,000 p/w eek ♦︎

O'Ptasia 12

85m Golden Yachts

85m   2018/2024

from $1,001,000 p/w eek ♦︎

Victorious 12

85m Ak Yachts

from $890,000 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 ♦︎

Alfa Nero 12

81m Oceanco

81m   2007/2024

from $812,500 p/w eek *

Elements 12

80m Yachtley

from $889,000 p/w eek ♦︎

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

from $998,000 p/w eek ♦︎

75m Feadship

from $900,000 p/w eek *

75m Abeking & Rasmussen

from $880,000 p/w eek

Starburst IV 12

from $1,010,000 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   2010/2024

Wayfinder 12

68m Astilleros Armon

from $375,000 p/w eek

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67m   2010/2020

from $540,000 p/w eek

67m Alloy Yachts

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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

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from $475,000 p/w eek

63m Halter Marine

63m   1978/2022

from $350,000 p/w eek

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Crewed Luxury Yachts in the Caribbean

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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 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!

Contact a specialist - available 7 days a week.

Yacht Name Search

Do you have a particular yacht in mind? We likely have it online and if not, email or call us for details. Search for it online by name here:

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LUXURY YACHT CHARTERS & SAILING VACATIONS

All-Inclusive Yacht Charters

All-Inclusive Yacht Charters are with a captain and your own personal chef they tailor your charter for a needs and requests. allows you enjoy sailing in beautiful large vessels such as; Catamarans, Monohulls and Power Yachts designed for comfort.

Kayak, snorkel, sail, scuba dive, paddle-board, fish, island hop, or simply relax aboard a Caribbean yacht charter. We’ve listed just a few reasons below:

Fully Crewed, Catered & Private Sailing Yacht Charters Tailored for You & Your Guests

• Private Sailing Vacation
• Create Your Own Custom Itinerary
• Visit Untouched Islands
• Different Caribbean Destinations
• Unforgettable Memories
• Fully Prepared Meals by Your Own Private Chef
• Underwater Adventures with Sea Life

We Look Forward to Welcoming You Aboard!

Explore Destinations like the British Virgin Islands, St. John, Grenadines, Bahamas, and St. Marten!

All-Inclusive Yacht Charters are with a captain and your own personal chef they tailor your charter for a needs and requests. allows you enjoy sailing in beautiful large vessels such as; Catamarans, Monohulls and Power Yachts designed for comfort.  For more information, please visit our: Frequently Asked Questions.

Choose a vessel from our inventory:

FEATURED YACHT CHARTERS

• Sleeps 12 Guests
• 7 Kings, 1 Twin

• 157′ Mega Yacht
• 2 Kings, 2 Queens,
• 2 Doubles, 2 Twins, 2 pullman

• Sleeps 8 Guests
• 3 Queens, 1 Twin

BLUE HORIZON

• Sleeps 6 Guests
• 2 Kings, 1 Queen

POPULAR YACHT DESTINATIONS

Other Yacht Charter Destinations

• Florida Key’s
• St. Thomas, USVI
• British Virgin Islands

DAY CHARTER BOAT RENTALS

Scout in the Virgin Islands

Full-day charters 9:30 – 4:30 PM. US Virgin Islands or the British Virgin Islands $1800. Bar hop or visit exclusive beaches while you stop and snorkel along the way!

Our 38′ Scout comfortably holds 6+ passengers, allowing plenty of room to lay out on the sun deck or relax in the shade while enjoying a drink and listening to your favorite music.

1/2 Day or Full Day Charters

• Captain and Crew
• Complementary snorkel equipment and fins
• Coolers stocked with Ice, water and assorted beer.
• Abundance of cushioned seating and lounging areas in shade or sun.
• Dry storage for your personal items and gear.
• Full size restroom
• All required USCG approved safety equipment, and extra features not required by law.
• Food, Liquor, Fuel and Crew Gratuity is NOT included.

Fishing in the Virgin Islands

Everyday is a great day to book a fishing excursion. We can give you the fishing trip of a lifetime. Whether you are an experienced fisherman or just getting started the  mahi-mahi, tuna, wahoo, and big marlin await.

We have all the latest and best fishing gear, outriggers, navigation and sonar, along with some of the best and most experienced captains in the islands. Whether you choose a half day (3.5 hours) or a full day (7 hours) off shore trip, you’re guaranteed to have a good time.

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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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282.2ft / 84m

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223.7ft / 67m

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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162ft / 48m

Sweet Escape

130ft / 39m

116ft / 34m

Caribbean Catamaran Charters

105ft / 31m

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Caribbean Crewed Sailing Yacht Charters

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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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.

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The best crewed yachts carefully vetted by our team.

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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.

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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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• Spirit Airlines Has More New Nonstop Flights to San Juan, Puerto Rico
• American Airlines Is Adding More Daily Flights to St Thomas, USVI
• Avelo Airlines Just Kicked Off Two New Nonstop Routes to Puerto Rico
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Book an unforgettable crewed yacht charter vacation.

View available yachts:.

Book with the Caribbean specialists. For over 19 years we have been a leading yacht charter brokerage connecting groups like yours with the best crewed yachts available for charter in the Caribbean including the Virgin Islands / BVIs / USVIs, Leewards, Grenadines and Bahamas.

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

Start planning your vacation today!

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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Specials and last minute discounts:.

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.

See all of the current crewed yacht charter specials and discounts.

Our customers say it best. Check out their feedback.

Stephen M, aboard Catamaran Salty Dog , February 2024  sailing the Virgin Islands

Max M, aboard Catamaran Moon Shadow , February 2024  sailing the British Virgin Islands

Mackie M, aboard Catamaran Gambit , January 2024  sailing the British Virgin Islands

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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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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

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10 Best Caribbean Yacht Charters

Setting sail on one of the 10 best Caribbean yacht charters feels like entering a...

Table of Contents

Setting sail on one of the 10 best Caribbean yacht charters feels like entering a picture-perfect paradise, with endless blue waters and each island boasting its tropical charm. In this article, we’ll show you some of the best boats for Charter in the Caribbean—the list of a few top boats to charter and the best destinations in the region. 

Brief Overview of the Caribbean as a Yacht Charter Destination

With its warm climate, gentle trade winds, and crystal-clear waters, the Caribbean has long been synonymous with luxury yacht charters . Stretching from the Florida Keys in the north to the coast of Venezuela in the south, this vast expanse of sea encompasses thousands of islands, each with its unique allure. Explore the possibilities with the top 10 Caribbean yacht charters.

From the bustling harbors of St. Thomas to the secluded anchorages of the Grenadines, the Caribbean offers endless opportunities for exploration and adventure.

Importance of Choosing the Right Yacht for Your Top Caribbean Charter

Your choice of yacht sets the stage for your entire Caribbean odyssey, shaping your experience in subtle and profound ways. Whether you’re seeking a lavish escape aboard a superyacht or a more intimate voyage on a classic sailing vessel, selecting the suitable vessel is paramount to ensuring a memorable journey. Factors such as type, size, amenities, crew expertise, and onboard services all play a role in determining which yacht best suits your needs and preferences.

What to Look for in a Yacht or Boat for Charter in the Caribbean

When considering one of the top 10 picks for yacht charters in the Caribbean, it’s crucial to consider several factors to ensure a seamless and enjoyable experience. The type and size are often a primary consideration, with larger vessels offering more space and amenities, while smaller boats provide a more intimate setting.

Additionally, consider the expertise and professionalism of the crew, as they will play a crucial role in guiding your journey and attending to your needs. Amenities such as water toys, entertainment systems, and onboard chefs can also enhance your charter experience, providing opportunities for relaxation and recreation throughout your voyage.

Top 10 Caribbean Yachts for Charter

Max of 7 selections

10 3 121.00 Ft

• TAIL LIGHTS

12 3 116.00 Ft

Name of the Yacht

Description and Unique Features

• Size & Year : 121.00 Ft, built in 2013
• Accommodation : 5 cabins for 10 guests, including a full-beam master suite with 180-degree views.
• Crew : A team of 7, led by Captain Thomas Gray, ensuring an extraordinary adventure

Amenities and Services

• Entertainment : Onboard WIFI, TV & iPads in all accommodations, and a variety of water toys
• Water Toys : Jetskis, paddleboards, kayaks, and more for an exciting aquatic experience

Pricing and Availability

• Rates : Starting at $105,000 – $135,000 per week.
• Rates are plus Expenses
• Cruising Areas : Bahamas in winter; Caribbean Virgin Islands (US/BVI). Caribbean Leewards in summer.
• Size and Year : A majestic 116.00 Ft yacht built in 2011.
• Crew and Capacity : Operated by a dedicated crew of 6, it can comfortably accommodate 12 guests.
• Accessibility : While not wheelchair accessible, it welcomes children and permits smoking.
• Accommodations : Features 5 staterooms, including a private master suite and VIP suites, all with en-suite bathrooms.
• Entertainment : Equipped with a media room, Jacuzzi, and water toys like jet skis and paddleboards.
• Connectivity : Offers high-speed LTE internet at sea, with optional services for enhanced bandwidth.
• Rates : Available from $80,000 to $90,000 weekly.
• Locations : Cruises through the Caribbean, Bahamas, and Virgin Islands, with preferred pickup in Nassau.

• NAUTI NICKEL

10 4 80.00 Ft

8 4 78.00 Ft

• Size and Build : An impressive 80-foot luxury yacht built in 2023.
• Accommodation : The yacht offers 5 cabins, including 1 King, 3 Queens, and 2 Twins, each with AC, TV, and sound devices.
• Unique Feature : The master cabin boasts a private balcony over the water.
• Entertainment : Equipped with onboard WIFI, satellite TV, ice maker, and a range of water toys, including a dinghy, water skis, jet skis, and paddleboards.
• Crew : Led by the experienced Captain Suzy Acevedo, with a dedicated chef, first mate, and stewardess to enhance your experience.
• Rates : Starts at $81,840 – $105,000 per week.
• Additional Rate Details : Christmas: $125,000 New Years: $130,000
• Rates are Caribbean Terms: Inclusive Taxes, re-location fees, cruising permits, and licenses may be extra.
• Availability : Serves the Caribbean region with preferred pickup at Yacht Haven Grande, USVI.
• FRENCH WEST
• Size and Build : The French shipyard Lagoon built a stunning 78-foot luxury yacht in 2020.
• Accommodation : The yacht offers flexible accommodation for up to 8 guests in 4 cabins, including a master suite, one VIP cabin, one double cabin, and one twin cabin.
• Unique Feature : The yacht has a shallow draft and fast speeds, making it perfect for reef exploration.
• Entertainment : While the specific amenities and entertainment facilities are not specified, luxury yachts typically come equipped with a range of amenities for relaxation and entertainment.
• Crew : The yacht is capable of carrying up to 3 crew members onboard to ensure a relaxed luxury yacht charter experience.
• Rates : The charter rates start at $50,000 – $66,000 per week
• Rates are Plus Expenses
• Additional Rate Details : SUMMER 2024 Weekly rates: 2-8 guests $55 000 + 30% APA
• Availability : The yacht serves the Caribbean region all year round.

• ENDLESS HORIZON

8 4 80.00 Ft

• RELENTLESS II 80
• Size & Year : An impressive 80.00 Ft yacht built in 2022.
• Accommodation : Boasts 1 King Bed, and 3 Queen Beds, and accommodates up to 8 guests in 4 luxurious cabins.
• Crew : A dedicated crew of 4, including a South African/Australian captain with extensive sailing experience.
• Entertainment : Equipped with onboard WIFI and a variety of water toys, including paddle boards and a wakeboard.
• Cuisine : Offers a sample menu with a range of exquisite dishes, from breakfast to desserts, prepared by a chef with over 15 years of experience.
• Rates : Available from $80,000 – $90,000 per week.
• Rates are inclusive .
• Availability : Cruising areas include the Caribbean Leewards and Windwards, with a detailed availability calendar provided.
• Size and Build : An impressive 80-foot luxury yacht built in 2022.
• Accommodation : Offers a main king cabin and three queen cabins, with the option to convert three queen cabins into twins.
• Crew : A professional crew of four, including a captain with a rich sailing background, a chef with fine dining experience, a stewardess/masseuse, and an adventurous first mate.
• Comfort : Fully air-conditioned with individual room temperature control.
• Entertainment : Equipped with onboard WIFI, ice maker, and various water toys, including paddle boards and wakeboards.
• Dining : A sample menu crafted by the yacht’s chef showcases a range of exquisite dishes, from breakfast to dinner.
• Rates : The weekly charter rate starts at $94,000 – $100,000.
• Rates are Caribbean Terms: Inclusive
• Capacity : Can accommodate up to 8 guests, with an additional option for a young child.

6 1 116.00 Ft

12 4 43.00 m

• Experienced Crew : Led by Captain Simon Davison, with decades of sailing experience.
• Gourmet Cuisine : Chef Louise Martin specializes in Mediterranean cuisine with fresh, healthy ingredients.
• Adventure and Leisure : Chief Stewardess Katrina Hughes brings a wealth of knowledge in water sports and adventure.
• Luxurious Accommodations : Full Beam Master with queen bed, guest double, and twin staterooms, all with ensuite facilities.
• Comprehensive amenities: Bathrobes, slippers, hairdryers, and L’Occitaine products are provided.
• Diverse Menus : Children’s menus, snack menus, late-night munchies, and dietary options available.
• Rates : Available from $65,000 – $74,750 per week.
• R ates are plus Expenses
• Cruising Areas : Sails in the Caribbean Leewards, Caribbean Windwards.
• Size & Year : A majestic 141.00 ft sailing yacht built in 2014.
• Accommodations : Offers luxurious quarters with fine wood paneling and modern conveniences, ensuring a blend of history and comfort.
• Crew : Led by the experienced Captain Seth Salzmann, known for his exceptional guest experiences and sailing prowess.
• Entertainment : Equipped with onboard WIFI, ice maker, and various water toys including a Williams Jet Tender, kneeboard, and paddleboards.
• Comfort : Ensures guest comfort with amenities like snorkel gear and high overheads filled with natural light.
• Rates : Available from $68,000 – $75,000 per week.
• Locations : Sails are available in various locations, including the Caribbean, Bahamas, and several U.S. coastal areas, depending on the season.

• AUGUST MAVERICK

12 1 92.00 Ft

• Size and Year : A majestic 92.00 Ft yacht built in 1978.
• Accommodation : Offers a large master suite with a king bed, twin cabins, and multiple showers and washbasins.
• Crew : Led by Head Captain Shawn Deweese, a highly experienced and qualified naval professional.
• Water Activities : Equipped with water skis, paddle boards, snorkel gear, and more for an adventurous experience.
• Comfort : Fully air-conditioned with spacious saloon, pilot house, and ample deck space for relaxation.
• Rates : Weekly charter rates are inclusive.
• Locations : Available in the Caribbean Virgin Islands during winter and summer.
• Luxury and Comfort : An 80-foot luxury yacht built in 2023, SÓL offers a blend of elegance and cutting-edge design. It accommodates up to 8 guests in 4 spacious ensuite staterooms, featuring a king-sized primary cabin and three queen-sized cabins, each intricately designed for maximum space and comfort.
• All-Inclusive Experience : Guests can enjoy a range of amenities, including onboard WIFI, an ice maker, adult and children’s water skis, paddle boards, wakeboards, and snorkel gear. The yacht also provides organic bedding, luxury, non-toxic personal care products, and hairdryers in each ensuite.
• Exclusive Rates : SÓL is available for charter at a weekly rate starting from $92,500 plus expenses, with the highest rate being $100,000 per week plus expenses. The booking calendar lets you check the yacht’s availability for the desired dates.

How to Book One of the 10 Best Caribbean Yacht Charter

Interested parties can start their dream vacation by contacting CKIM GROUP Inc. at 1321-777-1707 or via email.

Top 10 Caribbean Yacht Charters | Destination Highlights

The Caribbean is a vast and diverse region comprising countless islands, each with its distinct personality and allure. From bustling ports to secluded hideaways, here are some of the top destinations to explore aboard one of the top 10 Caribbean yacht charters:

St. Maarten / St. Martin

Known as the “Friendly Island,” St. Maarten is a vibrant destination renowned for its lively atmosphere, beautiful beaches, and duty-free shopping. The island is divided between French and Dutch territories, each offering its unique attractions. Visitors can stroll along Philipsburg’s bustling boardwalk, explore Marigot’s historic forts, or indulge in water sports and beachside relaxation at popular spots like Orient Bay and Maho Beach.

St. Vincent and The Grenadines  

Comprising a string of idyllic islands and cays scattered across the southern Caribbean, the Grenadines offer a serene escape from the hustle and bustle of modern life. Explore the top 10 Caribbean yacht charters and discover the picture-perfect beaches of Bequia and the uninhabited Tobago Cays, or hike through the lush hillsides of Mustique and Canouan. This secluded archipelago is a haven for yachters seeking tranquility and natural beauty.

Antigua  

With its rich maritime history, stunning beaches, and vibrant culture, Antigua is a must-visit destination for yacht enthusiasts. Explore the historic Nelson’s Dockyard, a UNESCO World Heritage Site, and immerse yourself in the island’s colonial past. For beach lovers, the powdery sands of Jolly Beach and Half Moon Bay offer ample opportunities for sunbathing, swimming, and water sports. 

The British Virgin Islands (BVI)  

The British Virgin Islands are a sailor’s paradise, boasting some of the best sailing conditions in the world and a plethora of secluded anchorages and pristine beaches to explore. Discover the top 10 Caribbean yacht charters and sail from the iconic Baths of Virgin Gorda to the legendary beach bars of Jost Van Dyke.

Each island offers its unique charm and attractions, whether you want to snorkel among colorful coral reefs, hike to breathtaking viewpoints, or simply relax and unwind in the laid-back island atmosphere.

St. Lucia  

Famed for its dramatic landscapes, lush rainforests, and iconic Pitons, St. Lucia is a Caribbean gem waiting to be discovered. Explore the UNESCO-listed Soufrière Marine Management Area, home to vibrant coral reefs and diverse marine life, or hike through the verdant interior to discover hidden waterfalls and panoramic vistas. For a taste of local culture, don’t miss the colorful markets and lively street festivals of Castries and Rodney Bay. 

The Bahamas  is not in the Caribbean, but it is a unique destination for yachting.

Comprising over 700 islands and cays scattered across the Atlantic Ocean, the Bahamas offers endless opportunities for exploration and adventure. From the bustling streets of Nassau to the secluded beaches of the Out Islands, there’s something for everyone in this tropical paradise. Snorkel among shipwrecks, swim with dolphins, or simply relax on the soft sands of world-renowned beaches like Pink Sands Beach and Treasure Cay. 

Dominica  

Nicknamed the “Nature Island,” Dominica is a paradise for outdoor enthusiasts and eco-adventurers. Explore lush rainforests, hidden waterfalls, and bubbling hot springs as you hike through the island’s pristine interior. Dive among vibrant coral reefs, paddle through mangrove swamps, or embark on a whale-watching expedition to encounter these majestic creatures in their natural habitat. 

Discover the bustling streets of St. Maarten or relax on the quiet beaches of the Grenadines—the Caribbean has plenty of amazing experiences waiting for you on a yacht charter trip. Whether you’re after some downtime, adventure, or cultural vibes, these different places offer something for everyone to enjoy. 

Seasonal Considerations for Your Top 10 Caribbean Yacht Charter

While the Caribbean enjoys pleasant weather year-round, certain times of the year are more conducive to yacht charters than others. From December to April, the winter months are considered the peak season, with balmy temperatures and numerous events and festivals. However, spring and fall shoulder seasons offer fewer crowds and more affordable prices, making them ideal for those seeking a quieter, more budget-friendly experience. 

Expert Advice for Your Top 10 Caribbean Yacht Charters Adventure

• Plan Ahead: Start researching and booking your yacht charter well in advance to secure your preferred dates and vessel. 
• Communicate Your Preferences: Be clear about your expectations and preferences with your charter broker, crew, and fellow guests to ensure a smooth and enjoyable experience for everyone. 
• Pack Wisely: Pack light, focusing on essentials such as sunscreen, swimwear, and casual attire. Don’t forget any necessary medications or personal items. 
• Stay Flexible: While having a rough itinerary in mind is essential, be open to spontaneity and unexpected discoveries along the way. 

Any of the top 10 Caribbean yacht charters offers the perfect blend of luxury, adventure, and relaxation. They allow you to explore some of the world’s most beautiful destinations in style and comfort. You’ll embark on a truly unforgettable journey by choosing the right vessel, planning, and following expert tips.

How Far in Advance Should I Book my Yacht Charter Vacation

Depending on the time of the year you wish to vacation it is important to book at least six to nine months in advance.

Are children allowed on yacht charters?

Many yacht charters are family-friendly and offer amenities and activities suitable for children of all ages, but it’s always best to check with the charter company beforehand.

What if I have dietary restrictions or preferences?

Most yacht charters can accommodate dietary restrictions and preferences with advance notice, so communicate your needs to the crew using The Preference Form before your trip begins.

Are pets allowed on board?

It depends on the yacht and owner’s policies. Some yachts may allow pets, while others may not. If you wish to bring a pet, kindly inform us, and we’ll check with the yacht owner to see if it’s possible.

Do I need Travel Protection?

We recommend that you protect your vacation investment against various possible losses over which you have no control by purchasing travel protection. We will provide travel protection quotes based on the households on the charter and each person’s date of birth. It is necessary to send us this information.

Please Note: To be eligible for the waiver of pre-existing medical condition exclusion, the protection plan must be purchased within 15 days (Travel Basic) or 21 days (Travel Select) from when you make your initial trip deposit. However, the plan can be purchased anytime before departure.

The product descriptions are only summaries and may be changed without notice. The full coverage terms and details, including limitations and exclusions, are contained in the insurance policy.

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Caribbean Sailing Charters

This stunning cruising ground is everything you would imagine and so much more. In the British Virgin Islands (BVIs), Caribbean sailing yacht charter guests can spend their days snorkelling vibrant coral reefs before visiting the famous Soggy Dollar Bar - known for its intoxicating Painkiller cocktail - for a night you’ll never forget.

Caribbean sailing charters.

A sailing holiday in the Windward Islands makes for a bounty of wild experiences; allow the scent of exotic spice to enchant you as splash in Grenada’s crystal-clear waters, or discover real island living in Barbados.

In the Leeward Islands, St Kitts promises rugged adventure while  Caribbean sailing holidays  to Antigua offer a chic escape complete with Michelin-Star cuisine. The unspoiled Grenadines are the place to come if you seek undisturbed relaxation, the most untouched of all the Caribbean island groups.

Oyster offers sailing yacht charters exploring every one of these blissful regions. Read on to learn more.

CRUISING GUIDE: CARIBBEAN SAILING YACHT CHARTERS

The best time to visit the Caribbean by sailing yacht charter is between December and April. Although the region is known for having a permanently glorious climate, averaging between 24-29°C/75.2-84.2°F all year round, a visit during these months offers lower humidity and less chance of rainfall. It also falls outside of the June-November hurricane season. You can expect temperatures of around 26°C/78.8°F and blissfully calm waters, perfect for bathing away your troubles or getting your heart racing with some exhilarating watersports.

Some of the most popular times for crewed Caribbean sailing yacht charters include the Christmas and New Year’s period and the Easter weekend when the islands fill up with festivities. You will discover more secluded sailing destinations and deserted beaches outside of these peak holidays, but the festive magic is hard to beat. The choice is yours...

Maximising your island-hopping experience onboard a Carribean sailing yacht charter allows you to explore every little bay that takes your fancy. Drop anchor by tiny secluded coves and discover deserted islands where you really can get away from it all.

For skippered Caribbean sailing holidays, look no further than Oyster. Our beautiful boats are light and spacious with luxurious furnishings that prioritise comfort without compromising on practicality. Large windows below decks mean you’ll be able to spot every single palm tree that dots the horizon, while our highly-professional crew come equipped with a local’s knowledge of every part of the Caribbean.

Explore this stunning region on one of our  luxury sailing yachts , or read on to learn about sailing the beautiful island groups of the Caribbean.

Sailing in the British Virgin Islands

An iconic cruising ground for Carribean sailing holidays, the BVIs are not to be missed. With nightlife that will have you dancing until dawn, seafood restaurants with fresh tuna and gin-clear waters offering perfect conditions for snorkelling and diving, this is the epitome of island living. Sail out to the caves at Norman Island to swim amongst exotic sea life and marvel at the vibrant colours. For charter guests who want nothing more than to lie on the sand and relax, cruise over to Anguilla, where the island’s flat topography makes for some truly phenomenal beaches. As the sun begins to set, head to The Rum Bar at Cooper Island, or for those who want to party all night, why not hop between the many lively bars on Jost Van Dyke.

The BVIs provide a delightful climate throughout the peak charter season: a perfect escape from the colder weather of the Northern Hemisphere.

Sailing in the Windward Islands

The Windward Islands deliver surprise after surprise on any Carribean sailing holiday, with each island full of its own unique character. St Lucia promises a vibrant history and rugged landscape - hike the Pitons for some truly incredible views across the islands and out to sea. Bequia is considered by some as the perfect Caribbean island, its difficult to get to by aeroplane meaning it has been protected from mass tourism, preserving all of its natural beauty. Glamourous Mustique is the favourite holiday spot of A-List celebrities and supermodels. However, despite its famous visitors, this three-mile haven is surprisingly low-key, with only one (extremely elegant) hotel on the island.

Authentic Caribbean living and jaw-dropping natural beauty await in the Grenadines - a 35-island region that lies within the Windwards. Snorkel in the Tobago Cays to meet friendly marine turtles and revel in the untouched landscape. Head to Mayreau for the wild nightlife and swim at best-kept-secret beach Salt Whistle Bay. Try your hand at kiteboarding on Union Island, and hang out with the locals in this laid-back set of villages. Caribbean sailing yacht charterers will love the variety of experiences that await in this cruising ground.

Head to the Windward Islands from December through to April to experience them at their best, with a multitude of fantastic events across all the islands. Look out for the Barbados Film Festival, now in its third edition and normally held in late January, or the lively Carriacou Carnival in mid-February. Also, visit in February to experience the yearly St. Vincent Yacht Club Regatta, or in March for the Saint Vincent’s Blues and Rhythms Festival.

Sailing in the Leeward islands

The Leeward Islands are famous for their good sailing winds, making them a must-visit destination for experienced sailors or those on skippered Caribbean sailing holidays, where the crew will guide your vessel while you simply relax. Head to Antigua, one of the most important superyacht hubs in the Caribbean, for unmatched glamour and a rich history. Don’t leave without touring Nelson’s Dockyard, the preserved 18th-century base of the British Fleet in the West Indies.

As the smallest landmass ever to be divided between two nations, St Martin/St Maarten offers a chance to experience both French and Dutch culture while revelling in the island’s majestic green peaks and crystal-clear waters. Heavenly St Barts has not one but fourteen gorgeous beaches at which to stretch out and do nothing or to get your pulse racing with some exhilarating water sports. Meanwhile, on St Kitts and Nevis, lose yourself in sugar plantation history at the UNESCO-protected Brimstone Hill Fortress National Park. This is an island group for those with an adventurous spirit, but it wouldn’t be a Caribbean sailing yacht charter destination without also being packed full of amazing beaches upon which you can soak up the sun.

In peak sailing season, the Leeward Islands offer the lowest humidity of all the Caribbean islands - perfect for keeping cool during those more challenging hikes - and temperatures average between 27°C/81°F and 35°C/95°F, ideal for lazy days on the beach.

Learn more about how to charter a sailing yacht in the Caribbean with Oyster. Discover  Oyster luxury sailing yachts for charter  or contact Oyster Charter Manager, Fiona McCarthy to begin planning your trip.

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BVI or USVI Sailing: Where to Book Your Next Caribbean Yacht Adventure

You’ve made up your mind: your next sailing adventure will be in the Caribbean. The gorgeous waters, gentle trade winds, and sun-drenched islands are calling your name. 

But now comes the real challenge – BVI or USVI? Just how are you supposed to decide between the British Virgin Islands (BVI) or the U.S. Virgin Islands (USVI)?

While we don’t believe you have to choose ( see here for our argument for combining the two ), it’s true that picking BVI or USVI means you can get a deeper experience when you pick just one.

We’re here to help you better understand the difference between the two, and help you make the choice. Among the team of Waypoints Yacht Charters Specialists, we’ve sailed these waters countless times, dropped anchor in hidden coves, and toasted sunsets from every angle. 

Before you set sail on your next yachting adventure, let’s dive into what sets these destinations apart, from the sailing conditions and culture to the natural offerings. Our goal? To help you decide which Virgin Islands – British or U.S. – is the right fit for your next Caribbean sailing escape. 

British Virgin Islands (BVI) Sailing

The British Virgin Islands are renowned for their exceptional sailing conditions, making them a favorite among seasoned sailors and newcomers alike. 

The archipelago’s layout creates a sailor’s playground, with short passages between islands and abundant sheltered anchorages.

Popular destinations in the BVI include the famous Baths of Virgin Gorda, where massive granite boulders create a labyrinth of grottoes and pools. 

The atmosphere of Jost Van Dyke draws visitors to its legendary beach bars, while Norman Island’s caves inspire tales of buried treasure.

Thanks to its history, the BVI offers a unique blend of British and Caribbean culture. Must-experience attractions include:

• Legendary Painkiller at Soggy Dollar Bar – Sail into White Bay on Jost Van Dyke and swim or dinghy ashore to this iconic beach bar. Sip the original Painkiller cocktail, a blend of rum, coconut, pineapple, and orange juices, while your toes sink into powdery white sand. The bar’s laid-back atmosphere and stunning views make it the quintessential Caribbean experience.
• Virgin Gorda Copper Mine Ruins – Flip the calendar back to the 19th century as you explore these atmospheric ruins perched on Virgin Gorda’s rocky southern tip. Wander among the stone walls and rusted machinery, imagining the bustling activity of Cornish miners who once sought their fortunes here. The site offers breathtaking views of the Caribbean Sea, perfect for a sunset photo opportunity.
• Trellis Bay Full Moon Party – Time your visit to coincide with this celebration of art, music, and fire on Beef Island. As night falls, massive metal sculptures crafted by local artists burst into flame, illuminating the bay. Dance to live music on the beach, sample local cuisine from food stalls, and join fellow sailors in a night of unforgettable island revelry.

For those seeking the perfect anchorage, popular spots include:

• The Bight at Norman Island – Drop anchor in this sheltered bay, rumored to be the inspiration for Robert Louis Stevenson’s “Treasure Island.” Spend the day snorkeling the nearby caves, teeming with colorful fish and coral formations. As evening approaches, swim or dinghy to the famous Willy T floating bar and restaurant for a night of pirate-themed merriment.
• White Bay on Jost Van Dyke – Sail into this postcard-perfect bay, where a crescent of soft white sand is fringed by swaying palms. The calm, crystal-clear waters make for excellent swimming and snorkeling. Ashore, a string of casual beach bars offers the perfect spot to watch the sun dip below the horizon, rum cocktail in hand.

Hidden gems worth discovering:

• Manchioneel Bay on Cooper Island – Escape the crowds at this quiet anchorage on Cooper Island’s northern shore. The bay’s protected waters are ideal for paddleboarding or kayaking along the mangrove-lined coast. Ashore, visit the eco-friendly Cooper Island Beach Club for craft beer from their microbrewery and rum tasting sessions featuring over 100 Caribbean rums.
• Diamond Cay National Park – Make your way to this pristine marine protected area near Jost Van Dyke. Anchor off the tiny islet and dinghy ashore to hike the short trail to the Bubbly Pool, a natural jacuzzi formed by waves crashing through a rocky crevice. Snorkel in the crystal-clear waters around the cay, keeping an eye out for sea turtles and tropical fish darting among the coral reefs.

If you’ve been thinking about getting to the BVI, now’s the time to start planning for 2025 .

U.S. Virgin Islands (USVI) Sailing

The U.S. Virgin Islands provide a different yet equally special sailing experience. With three main islands – St. Thomas, St. John, and St. Croix – the USVI offers a mix of developed areas and unspoiled natural beauty.

Sailing conditions in the USVI can be more challenging than the BVI, with longer passages between islands and more exposure to open water. 

This makes it an excellent choice for those looking to sharpen their sailing skills. The USVI’s cultural highlights blend American influences with Caribbean traditions. 

Must-visit islands and hotspots include

• Magens Bay, St. Thomas – Come explore this horseshoe-shaped bay, often hailed as one of the world’s most beautiful beaches (we see you, Travel + Leisure ). As you approach, you’ll be struck by the mile-long stretch of powdery white sand framed by verdant hills. For the adventurous, hike the nature trail to the hilltop for a breathtaking panoramic view of the bay and surrounding islands.
• Virgin Islands National Park, St. John – See for yourself why this island is often called the crown jewel of the Caribbean. With two-thirds of St. John protected as a national park, you’ll find an unspoiled paradise of lush forests, hidden coves, and pristine beaches. Sail into Trunk Bay to snorkel the underwater trail, spotting colorful fish and coral formations. 
• Buck Island Reef National Monument, St. Croix – Set a course for this uninhabited island off St. Croix’s northeast coast for a world-class snorkeling experience. The crystal-clear waters reveal an underwater wonderland of elkhorn coral barriers, vibrant reef fish, and even sea turtles. Follow another underwater trail of plaques that guide you through this living museum. After snorkeling, relax on the pristine white sand of Turtle Beach, keeping an eye out for brown pelicans diving for their lunch offshore.

In addition to the main attraction islands, these are a few of our favorite experiences: 

• Historic Charlotte Amalie – Wander through cobblestone alleyways lined with Danish colonial architecture, local markets, and duty-free shops. Climb the famous 99 Steps for a panoramic view of the harbor, then cool off with a tropical cocktail.
• Quelbe Music Experience – Enjoy the soul-stirring rhythms of the USVI’s official musical style. Attend a live performance at a local festival or beachside bar, where the infectious blend of African, European, and Caribbean influences will have you moving to the beat of centuries-old traditions.
• Annaberg Sugar Plantation Ruins – Step back in time as you explore the haunting beauty of this 18th-century sugar plantation on St. John. Walk among the weathered stone structures, imagining the bustle of colonial life while taking in sweeping views of Leinster Bay and the British Virgin Islands beyond.

For your sailing itinerary, popular routes include:

• St. Thomas to Cruz Bay Crossing – Set sail from Charlotte Amalie harbor, watching the urban landscape give way to lush green hills as you navigate the Sir Francis Drake Channel. Approach St. John’s Cruz Bay, where colorful buildings and swaying palms welcome you to this more laid-back island paradise.
• East End Cays Adventure – Chart a course around St. Thomas’ eastern tip, where a string of captivating cays awaits. Drop anchor at Cas Cay to snorkel in crystal-clear waters teeming with tropical fish, then enjoy a sunset barbecue on the powder-soft sands of Water Island.

Off-the-beaten-path gems:

• Water Island Serenity – Discover the tranquil charms of the “fourth” Virgin Island, just a short sail from St. Thomas. Anchor in Honeymoon Beach’s turquoise waters and spend the day lounging on uncrowded shores, snorkeling reefs, or hiking to World War II-era Fort Segarra for panoramic views of the surrounding islands.
• Salt River Bay Expedition – Venture to St. Croix’s north shore to explore this unique ecological and historical treasure. Kayak through mangrove forests in the only known site where Christopher Columbus landed in what is now U.S. territory. Dive or snorkel the underwater canyon, home to rare bioluminescent organisms that create a magical night time display.

For more on sailing in the USVI, we’ve got a list of our favorite hot spots and hidden gems here .

Comparing BVI and USVI Sailing Experiences

While both destinations offer Caribbean charm and excellent sailing, key differences set them apart. The BVI tends to have more consistent winds and calmer seas, ideal for leisurely island-hopping. The USVI, with its longer passages, caters to those seeking a bit more adventure in their sailing.

Culturally, the BVI retains a stronger British influence, evident in its customs and traditions. 

The USVI, as an American territory, offers a unique blend of Caribbean and U.S. cultures. 

For instance, you’ll find cricket matches in the BVI, while American sports are common in the USVI.

The BVI is known for its numerous uninhabited islands and cays, perfect for those seeking seclusion. 

In contrast, the USVI offers a mix of bustling ports and untouched natural areas, providing a more varied experience.

Planning Your Caribbean Yacht Adventure With Waypoints Yacht Charters

The most popular time to visit both the BVI and USVI is during the dry season, from December to April. However, sailing is enjoyable year-round, with the shoulder seasons offering fewer crowds and lower prices. For more on traveling during this period, check out our more extensive article here .

When booking with Waypoints Yacht Charters, you’ll benefit from our expertise in both destinations. 

Our team can help you choose between the BVI and USVI based on your sailing experience, desire for cultural experiences, and preference for developed or more secluded areas. Not only that, but we have charter bases in each. Read on to see what you can enjoy at each.

The Waypoints Yacht Charters Experience in USVI

The Waypoints USVI base is located at Frenchtown Marina in St. Thomas, just a 10-minute cab ride from Cyril E. King International Airport (STT). This prime location allows for easy access to the surrounding islands and a quick start to your USVI sailing adventure.

Embarkation begins at noon on the first day of your charter, with sleep aboard options available from 4:00 p.m. The Waypoints team provides comprehensive online briefings prior to your arrival, followed by an in-person review and chart briefing at the base.

Rae Ann A. shares her experience with Waypoints USVI:

“We have been chartering catamarans, both bareboat and crewed, for many years and from many charter companies – in the VI, the Bahamas and Europe. Our bareboat charter experience with Waypoints was the best we’ve ever had, from the initial call with the sales office all the way through to checking back in at the end of our journey. The staff at Waypoints is very professional and also very relaxed and friendly. Everyone went out of their way to give us a great experience.”

Why You’ll Love The BVI Waypoints Yacht Charters Base

The Waypoints BVI base is situated at Nanny Cay Marina on Tortola, providing an excellent starting point for your BVI adventure. Located on the south side of the island, about 3 miles west of Road Town, the base offers easy access to the surrounding islands.

Embarkation begins at noon on the first day of your charter, with sleep aboard options available from 5:00 p.m. The knowledgeable staff conducts thorough yacht briefings, typically lasting 45-90 minutes depending on the vessel size.

Getting to the base is convenient whether you fly into Terrance B. Lettsome International Airport (EIS) on Tortola or Cyril E. King International Airport (STT) on St. Thomas. From St. Thomas, you can take a ferry to Tortola, with private water taxi options available for a more personalized transfer.

Solomon G., a satisfied customer, wrote:

“We had an amazing experience on an 8-day bareboat charter with Waypoints Yacht Charters BVI. I can honestly say this was the best experience I have ever had with a bareboat charter company. Saying this boat was in pristine condition is an understatement. Anthony and his team are absolutely amazing.”

Another client, Peter F., said:

“Just completed a 10-day bareboat sail on Tupelo Honey and had a spectacular time. I cannot say enough praise for this ‘young/new’ company which is run by very experienced professionals who clearly know how to cater to every need for the charter sailor. The equipment is new and clearly well-maintained by very helpful and friendly staff all in a classic BVI setting of the well-positioned full service Nanny Cay Marina. There is no doubt we will be back.”

Why Choose Waypoints Yacht Charters?

Whether you choose the British Virgin Islands or the U.S. Virgin Islands, a Caribbean sailing adventure promises plenty of unforgettable experiences. The BVI offers easier sailing and a more laid-back atmosphere, while the USVI provides a mix of American comforts and Caribbean charm. 

Whichever you choose, Waypoints Yacht Charters is here to help facilitate your journey with our boutique approach and unparalleled local knowledge. Contact our Waypoints Yacht Charter Specialists today to start planning your Caribbean sailing escape in the BVI or USVI.

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The RORC Caribbean 600 - Antigua

The 2020 RORC Caribbean 600 Race will start on the 24th of February 2020 

Sailing fans from around the world are set to gather in the Caribbean for Antigua’s RORC (Royal Ocean Race Club) Caribbean 600 regatta event. Celebrating its 10th year, enthusiasts are looking forward to seeing the largest ever offshore fleets of sailing yachts compete against one another. This annual 600-mile-long race circumnavigates around 11 Caribbean islands, a challenge which all the participants relish.

CharterWorld provides the direct opportunity to rent a RORC Caribbean yacht charter boat to accommodate you and/or your corporate associates at this important sailing event. Please contact us here at your earliest to ensure you have access to the best luxury yacht charters available.

Last year almost 900 sailors including Olympic medallists and America’s Cup winners took part in the regatta. The upcoming 2020 event is bound to attract strong competition once again, record entry is expected.

The RORC Caribbean starts and finishes in Antigua. This race course is an enduring test of speed and agility for all those taking part, a real cracker of an event.  It weaves its way around Barbuda, St Kitts and Nevis then St. Barths before circling the superyacht playground of St. Martin, heading back down to Guadeloupe.

To round up the event on the final evening, a prize-giving ceremony is going to be held at the Antigua Yacht Club. The well -deserved winners will be presented with an exciting collection of silverware, decanters and medallions. Then it’s party time, Caribbean style into the early hours. 

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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.