sailboat charter annapolis

Picture Perfect Sailing

• Meet your Skipper

Sail in Annapolis, Book a Sailing Cruise Today

Enjoy quality time with family and friends sailing out of Annapolis. You'll fall in love with the Chesapeake Bay. Your sailing charter awaits. 

CHOOSE YOUR SAILING ADVENTURE

Sailing options.

With Picture Perfect Sailing, the options are virtually endless!

Your skipper will take you for a day sail in Annapolis for a few hours towards St Thomas Point Lighthouse or the Chesapeake Bay Bridge, or perhaps around Annapolis harbor. For a longer sailing charter, choose our all-day sailing experience or overnight. You'll find yourself sailing to Baltimore or Saint Michaels. Book a sailing cruise now, make the memories of a lifetime with your family and friends!

Day Sail: come sailing for a few hours

Duration: 3 hours (leaves and returns to Annapolis)

Starting at $650 for 2 guests. Your sailing charter includes: skipper, snacks & beverages. Please check rates and book a sailing cruise by clicking the button below.

Sunset Sails: come sailing as the sun goes down

Duration: 2.5 hours (leaves and returns to Annapolis)

Starting at $650 weekdays for 2 guests. Your sailing charter includes: skipper, snacks & beverages. Please check rates and book a sailing cruise by clicking the button below.

All Day of Sailing: come sailing on the Chesapeake Bay all day!

Duration: 6 hours (leaves and returns to Annapolis)

Starting at $1,550 weekdays for 2 guests. Your sailing charter includes: skipper, crew member, snacks, lunch & beverages. Please check rates and book a sailing cruise by clicking the button below.

Overnight Sailing: experience sailing and sleeping aboard!

Choose one or two overnights: (leaves and returns to Annapolis)

Single (one) overnight: typically departs at 10am, one overnight in Baltimore or St Michaels, with disembarkation at 5pm the next day. Variations upon request. Starting at $2,450 weekdays for 2 guests. Your sailing charter includes: skipper, hostess, lunches x 2, snacks, breakfast x 1 & beverages. 

Double (two) overnights: typically departs at 9am,  one overnight in Baltimore or St Michaels, second overnight at the dock back in Annapolis and disembarkation at 9am the next morning. Starting at $3,900 for 2 guests.  Your sailing charter includes: skipper, hostess, snacks, breakfast, lunch x 2 & beverages.

The prices displayed in the booking schedule include yacht fuel, dock fees, water, propane for cooking, yacht insurance, cabin linens & bath towels. 

What’s not included: water activities off the boat (due to insurance limitations) such as swimming, paddle boarding or dinghy use; dinners (plan dinners on shore); crew gratuity.

How to book a sailing cruise with an overnight? Contact us for availability and custom pricing.

*Rates vary by season. Holiday rates upon request. Special pricing for Navy families, veterans, and first responders.  Contact Picture Perfect Sailing for more information and to book a sailing cruise today!

The Sailboat

You'll sail aboard a Beneteau Oceanis 45, with extensive cockpit protected by canvas and well-appointed to accommodate up to 3 couple for overnight sailing in maximum comfort; a head (bathroom) with shower, a full galley (kitchen) and comfortable salon. Arguably the nicest charter boat to sail in Annapolis. Let the sailing adventures begin, book a sailing cruise now.

With Picture Perfect Sailing, your designated skipper (and mate, depending on your sailing option!) will lead the sailing charter: maneuver the boat, guide your visit of the Annapolis area on the water, and ensure the fun & safety of all! 

Meet your skipper .

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Elite Charters of Annapolis

Luxury yacht charter experiences.

Unique and Unforgettable Memories Await in Annapolis and on the Chesapeake Bay

Why Choose Elite Charters of Annapolis

Exclusive Yacht Charter Experiences

Let us host your next special occasion, cocktail cruise, relaxing weekend, or wedding cruise aboard one of our luxury yachts.  

Located in the heart of Annapolis, our professionally crewed charter yachts are easily accessible and create stunning and memorable experiences on the Chesapeake Bay. 

Our yachts are equipped with state-of-the-art amenities, including air conditioning, comfortable seating, and entertainment systems.

Professional Captains and Crew

Our crew members are experienced and knowledgeable about the Chesapeake Bay. They will ensure that you have a safe and memorable experience on your charter.

Muse - 87' Warren Yacht

• This sleek 87 ft sport yacht is available in Annapolis and the Chesapeake Bay.
• Invite up to 12 guests for half or full-day private yacht charters.
• She boasts beautiful teak decks, dual salons, and a spacious aft entertainment area.
• With a 5 ft draft, Muse can navigate secluded coves and anchorages.
• A 27-knot cruise speed ensures fast travel and exploration of multiple destinations.
• Overnight guest accommodations for six plus crew.

Shredder - 54' Eastbay

• Built by Grand Banks, the 54 ft Shredder is the quintessential Downeast-style cruiser.
• Accommodates up to 12 guests for half or full-day private yacht charters.
• Ideal for multi-day or week-long luxury Chesapeake Bay cruises for a couple in the spacious master stateroom.
• Perfect for day excursions to quaint Chesapeake Bay towns, romantic dinners, and water activities.

Firefly - 68' Azimut

• The Italian-designed and built Firefly turns heads with its sleek lines and lavish leather interiors.
• With a 6 ft draft, Firefly can access secluded Chesapeake Bay coves and shallow rivers.
• Features two spacious staterooms, making it an ideal overnight retreat for two couples or accommodating up to 12 guests on a day charter.
• Suitable for various experiences, from an elegant sunset cruise to a week-long excursion along the Chesapeake Bay, Annapolis, and Baltimore.
• Firefly ensures your private yacht charter is marked by style, comfort, and luxury.

Photo Gallery

The stunning yacht Muse at her winter home in Miami

Reserve Your Charter Today!

Get in touch.

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Send us a message to schedule your charter. We will get back to you soon!

326 1st Street, Suite 403, Annapolis, MD 21403

Mike Esposito / [email protected] 239-227-7879

Copyright © 2024 Elite Charters of Annapolis - All Rights Reserved.

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• Chesapeake Bay Itineraries
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Chesapeake Bay

• Virgin Islands
• St. Vincent & The Grenadines
• Browse our Fleet
• Meet Your Captains
• Charter Management
• Sailing Lessons

Celebrate or relax in style on a private yacht charter

Charter a luxury catamaran yacht for a few hours, days or weeks.

Enjoy the scenic views, sailing yacht charter amenities and the adventure that lays ahead for you and your guests. Our experienced captains provide local knowledge and nautical skills to ensure a safe and fun experience for everyone. We can’t wait to have you aboard!

Destinations

Charters available in these beautiful destinations

Key West, FL

The Abacos, Bahamas

U.S., British & Spanish Virgin Islands

St. Vincent & The Grenadines

Make your special occasion a one of a kind experience.

Our mission at Sail Away Catamarans is to provide you and your party a one of a kind experience. Chartering a private yacht is a fun and decadent way to celebrate birthdays, weddings, anniversaries and retirements. Or get the gang together for a family trip, bachelorette party, or a corporate event. Our experienced charter agents are standing by to help make your event a memorable one.

Book Today and Set Sail

Select a Yacht or Itinerary

Search for the yacht or find an itinerary that best fits your event.

Submit Request

" Book Now " to submit your preferences and make your payment. You will receive a confirmation number & email.

We Will Review

One of our specialists will call and review your booking with you as your date nears. Let’s go sailing!

"Can not recommend Sail Away Catamarans enough! I was planning a bachelorette party with 12 girls and they could not have been more accommodating. They were very responsive, reasonably priced and the day of went off without a hitch! ...the boat was just beautiful! All the girls had wonderful things to say and a great time!

Our Most Popular Itineraries

Sunset cruise on the bay, so maryland: crab feast + sail, overnight in annapolis or saint michaels, custom itinerary, book your sailing charter now.

Embark on Your Unforgettable Journey

Watermark immerses you in the history, culture, and fun of the Chesapeake Bay area more completely than any other tour or charter company.

Cruises and Tours in Annapolis & Baltimore

Unforgettable journeys start with Watermark, and we’ve been doing it for more than 50 years.

Experience the best of Annapolis and Baltimore with cruises, walking tours, private yacht charters, and field trips.

This Week's Cruises & Tours

• Annapolis Harbor & USNA Cruise — Available Daily
• Baltimore Sightseeing Cruise — Available Tues-Sun
• Day on the Bay to St. Michaels — Saturdays
• Colonial Annapolis Walking Tour (+USNA Option) – Fri-Sun
• Maryland State House Tour — Available Fri-Sun
• African American Heritage Tour 9/21
• Annapolis Sunset Cruise with Sister Midnight Band 9/21
• Historic Ghost Tour — Fridays & Saturdays

Embark on Your Own Watermark Journey

Public Cruises

• Enjoy being out on the water with a variety of cruises from 40 minutes to a full day.

Private Yacht Charters & Weddings

• Take your next event to the water; the perfect venue for any occasion.

Walking Tours & Guided Experiences

• Discover local history with your period-attired tour guide in Historic Annapolis.

Field Trips & Youth Programs

• Field trips that meet your curriculum, grade level, and programming needs.

Group Experiences

• Explore a variety of affordable cruises and tours for your group event.

Annapolis Water Taxi

• Climb aboard the Annapolis Water Taxi — the best way to get around Annapolis!

Why Watermark?

Watermark creates unforgettable journeys for tens of thousands of guests in Annapolis and Baltimore every year.

• A complete Annapolis and Baltimore experience
• Informative and fun, knowledgeable and helpful
• The most refreshing way to see the sights
• Unique educational field trips on land and water
• The most affordable way to get out on the water
• Meticulously maintained classic and elegant yachts
• Customized private yacht charters
• History comes alive in our museum without walls
• Family fun activities for all ages
• Highly trained, certified guides, captains, and crews
• Over 50 years of sharing the best of the Chesapeake

Follow Watermark on Instagram

@ watermarkjourneys . Sep 14

@kalebsanders and @sheenabrook for Water Taxi Karaoke 🚖🌊🎶 ...

@twinnieofficial and @sheenabrook for Water Taxi Karaoke 🚖🌊🎶 ...

@ watermarkjourneys . Sep 13

@dylanaltmanmusic and @sheenabrook for Water Taxi Karaoke 🚖🌊🎶 ...

@sheenabrook and @jacobricemusic for Water Taxi Karaoke 🚕🌊🎶 ...

@ watermarkjourneys . Sep 7

See you down at the dock 😎✌️ ...

@ watermarkjourneys . Sep 6

We`re only a week away from the @AnnapolisSongwritersFestival 🎸🎶 Climb on board Saturday, September 14th for Songwriters on the Severn and enjoy performances by @JulyMoonOfficial, @TheHeelsMusic, and @LukeBorchelt! Get your tickets 👇👇👇 https://watermarkjourney.com/events/songwriters-on-the-severn/ ...

@ watermarkjourneys . Aug 31

Wondering what to do with your three-day weekend? We`ve got plenty of ideas 😎 Visit our website to see what we have going on 👉 WatermarkJourney.com ...

@ watermarkjourneys . Aug 30

Grey skies can`t keep us from a fun time 😁🚢 ...

Watermark Staff over the last 50 Years

Watermark Team Since 1972

A family-owned business since 1972. Learn more about the growth and progression of Watermark.

Our Watermark Team Today

Interested in joining the Watermark family? Get to know our team here and view our open positions.

Guest Journeys

Creating unforgettable journeys for over 50 years.

Sailing Charters aboard the 'PINTITA' out of Annapolis & Baltimore

Make your next getaway a sailing adventure on the Chesapeake Bay!

Are you planning a birthday or anniversary celebration, planning a proposal, getting married or renewing your vows, or just want to enjoy the Annapolis or Baltimore skyline with a cold beverage while sailing?  Help raise and trim the sails, navigate, man the helm or simply take in the experience and sights while relaxing with a cold beverage. Come see what the allure of sailing is all about. The professional Captain and Crew of the ‘ PINTITA ’ can help make your next adventure a memorable one. 

We are currently booking private sailing charters for up to 20 passengers! 

We ask that you continue to support your local businesses and this Veteran owned small business needs your support and patronage.  Please book your private sailing charter soon for your next friends, family, and or corporate outings.  We are looking forward to harnessing the wind and creating memories with you.

Pla n to join us for the U.S. Navy Blue Angels in Annapolis during Commissioning Week in May, 2024

See our Charters page from the menu above

Call us now to book your getaway:

443-510-5756

The ‘PINTITA’ is perfect for:

Bachelor & Bachelorette Parties

Engagement Proposals

Anniversaries

Alumni Events

Company Events

Team Building

We offer many charters to meet your needs.

The 'PINTITA' Sailboat is licensed for groups of up to 20 persons! She has an all weather enclosed cockpit to keep you dry from passing showers! She is designed to make your outing as entertaining and comfortable as possible.

The PINTITA

Come sail the chesapeake bay..

Join us in Annapolis & Baltimore.  We hold a current USCG Certificate of Inspection for Private charters, meaning that she is inspected in her construction, equipment, and maintenance to rigorous federal standards.

PINTITA was ready to get going as we left her. A late afternoon westerly had piped up, and the flags were standing stiff at attention. Pintita chafed at her docklines. "Lets go!" she seemed to say. "I may not be a racehorse, but we'll have a good time in this breeze"  

                                                                                                      – Spreadsheet Magazine   

   

ANNAPOLIS, BALTIMORE AND CHESAPEAKE BAY CHARTER INFORMATION:

 443-510-5756

s [email protected]

For Onboard Vessel Instruction, Vessel Delivery or Captain / Crew Charter services aboard your vessel please visit Atlantic Maritime Services, LLC at:  AtlanticMaritimeServicesLLC.com

443-333-3511

Veterans Crisis Line 800-273-8255 

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• Annapolis: 410.263.8234
• Cape Cod: 508.524.9121
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A Grand Experience for All

Custom built for sailing, comfort and fun. Our cruising grounds are some of the most beautiful and historic in the country

Corporate Events

Special occasions, adventure & entertainment.

Custom built for sailing, comfort and fun, the Liberte is a grand experience for all. Our cruising grounds are some of the most beautiful and historic in the country. The captain and crew are dedicated to your safety, comfort and enjoyment.

USCG certified for 49 passengers. Music. Full bar. Every Sail is Unique.

One Great boat, two great locations

About the boat.

The schooner, Liberté, is based on Spa Creek in Annapolis, Maryland. During the summer months, she’s docked at the Patriot Party Boats pier in Falmouth harbor in Cape Cod, Massachusetts. Captain Chris and Jane had this vessel built just for them.

The original hull design by Dudley Dix is a Hout Bay 70, a two-masted gaff-rigged schooner intended as a heavy but fast offshore cruiser. Many alterations were made to the design, including adding a spoon bow, scaling down the lines to meet U.S. Coast Guard parameters, redesigning the deck layout and adjusting the rig to a three-masted staysail design.

Get In Touch Now

• © 2024 The Liberté
• All Rights Reserved
• Website Design & Marketing provided by Adventure Web Interactive

We sail April 19, 2024 to Nov 3, 2024

Sail Selina II

Relaxing chesapeake bay sailing tours, sailboat rides & sightseeing boat trips in st. michaels, md, we sail april 19,2024 to nov 3, 2024, clean & safe, thank you for supporting small business, our popular st michaels maryland sailing charters and relaxing chesapeake sailboat cruises.

• Most Popular
• Hour Glass 2 Hours
• Users 6 People
• User All ages
• Calendar Daily

2 Hour Relaxing Chesapeake Day Sail

Want to relax? Join our friendly crew and learn about St. Michaels while cruising in a comfortable well-maintained historic sailboat on the Chesapeake Bay. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy outdoor scenery on your personalized sailing boat tour!

Chesapeake Bay Champagne Sunset Sail

Experience a breathtaking Chesapeake Bay sunset while savoring a glass of Champagne or handcrafted beer or wine on this romantic St. Michaels, MD sunset cruise. Book now to embark on an unforgettable journey that’s perfect for couples looking for a unique and romantic date night activity.

Moonlight Cruise

Enjoy free Champagne while taking in the breathtaking beauty of a sunset or the rising of the moon on Chesapeake BY aboard this romantic Moonlight Cruise!

• User Ages 21+

St. Michaels Wine Tasting Cruise

Come aboard Sail Selina II in St Michaels MD and learn the basics of wine tasting and sample great vintages with Capt. Iris and her crew during this 2hr outdoor excursion.  Our wine cruise is just an hour from Annapolis, making it the perfect day trip.

Beer Tasting Cruises

Looking for a fun and refreshing way to quench your thirst with a cold beer while exploring the St Michaels area? Sit back and enjoy some great Maryland Craft breweries aboard the Selina II!

Private Sailing Lessons

Embark on an unforgettable sailing adventure with our seasoned team aboard the historic yacht Sail Selina II. Experience the freedom and exhilaration of sailing while learning new skills and building confidence on the water. This introduction to the basics that will transform the way you connect with mother nature.

• User Adults only

Marriage Proposal Engagement Cruise

♥Getting engaged♥? Surprise your fiancé with a nautical wedding proposal on a private yacht with this Engagement Package. If you’re looking for a creative engagement on a boat this is a unique way to pop the question!

• Users 6 or More

Nautical Wedding Package

Looking at weddings on a boat? Get married in St Michaels MD on a sail boat and have an unforgettable nautical elopement or sailboat wedding ceremony aboard Sail Selina’s yacht! You have two wedding packages to choose from:  boat weddings are either a Ceremony Under Sail, or a Wharf-Side Wedding.

Sail Selina Swag

Sail Selina has perfected the art of sailing, and now we’re proud to introduce our collectable high-quality logo apparel that will have you looking as good as you feel on the water.

Best Relaxing Luxury Sail Boat Tours on Chesapeake Bay

Looking for a relaxing Saint Michaels, Chesapeake Bay boat tour? Want to get out on the water, unwind and spend some time in nature? If you’re wondering about things to do in St. Michaels MD or seeking top attractions in St. Michaels Maryland, look no further than the luxury sailing yacht Selina II. Unique, upscale, and exclusive, she limits her passengers to just 6 guests for an intimate taste of the history of sailing.

With freshly varnished mahogany, brightly polished brass, and comfortable seating, let Sail Selina II, the premier sailboat in St Michaels, MD, be your sightseeing charter boat. Hop aboard and experience another time and place.

Come join us outdoors on the water for a relaxing 2-hour sailing trip on this nostalgic river boat cruise. Your St Michaels, Maryland sailboat ride includes a personalized informative tour with our knowledgeable 1st-class captains and friendly crew. We know you’ll love all the boating trips aboard our meticulously-restored historic 1926 sailboat Selina II, including romantic sunset cruises, our super popular day sails, and our specialty outings like sailing lessons, wine tasting tours in St. Michaels MD, beer tasting cruises, moonlight sails and more.

For private sailing tours, the Sail Selina II is docked at the Harbour Inn & Marina in the heart of St Michaels, MD, a charming eastern shore town known for its wonderful seafood restaurants and quaint small-town feel.

If you are looking for day trips to St. Michaels Maryland or if you want a sailing charter on the Eastern Shore of the Chesapeake Bay, Sail Selina II’s relaxing sailboat trips are just 90 minutes from Philadelphia, Baltimore and Washington D.C. and just 60 minutes from Annapolis.

Outdoors in nature, our sailing boat offers your choice of a public or a private boat ride in one of the best places to sail. Chesapeake sailing is known for its beauty and gorgeous sunsets. Your sailboat charter includes a boat sail through the harbor and then out into the Miles River for spectacular views and sometimes even wildlife viewing like Osprey & Bald Eagles. This year there have even been porpoise sightings.

Looking to relax? We are the St Michaels MD harbor cruises to choose!

Learn more about the history of our sailboat and all the fun outdoor activities in St. Michaels, MD here:

The #1 Boat Tour in St. Michaels on TripAdvisor!

A friend was visiting from Baltimore and we went sailing last night for the sunset cruise. It was amazing, the sailboat was gorgeous, the Captain and her first mate were exceptional, and the beauty of the river was breath taking. I am so glad I discovered Sail Selina II, I will be taking many friends and family members on this beautiful adventure when they come to visit me in Easton. Thank you for a remarkable memory and such a beautiful experience.

A golden opportunity to sail on a captain owned historic wood yacht! It was a dog day of August with precious little wind, yet we enjoyed every minute of our trip. Captain Iris was a gracious host, passionate generational owner, not only captain but articulate professor of both sailing and ship building. We highly recommend sailing aboard the Selina ll. The crew is fabulous as well.

Hubby and I spent a sunset afternoon on Selina 2 with Captain Iris and first mate Jesus. We had a lovely cruise drinking champagne and listening to Captain Iris talk about St Michael and the history of her family sail boat. What I loved was she was mentoring a future captain in the making - a twelve year old from the area who wanted to learn more about sailing. This is so worth it and I very much encourage you to go!

My wife and I had a great time on this vintage sail boat. The Captain and First Mate were great hosts teaching us a lot about sailing and the history of the bay at the same time. Loved that the boat holds only six guests at a time, only four aboard for our trip, making it a very intimate experience!

The two hour cruise In the company of Captain Iris, Crewman Chris, and four other guests provided the best evening of our August vacation. The generous hospitality (nice selection of wine and beer if champagne was not your preference) was supplemented by the unexpected and pleasant opportunity to observe several races and Captain Iris was generous with her knowledge of sailing the Tred Avon areas of the Chesapeake. The Salina II will see us again when we return.

Took a moonlight cruise on the Sail Selena II. Had a lovely evening star gazing, sipping wine, chatting with the other couple aboard. Cap’t Iris and her ever so sweet (and personable) first mate were both kind and knowledgeable. We enjoyed the evening immensely. We would recommend this outing without hesitation. Such a great experience!

Being a motor-head all of my life never really let me get the deep appreciation of the sea as I experienced when I sailed on the Selina II. To cruise along with nothing but the sound of the waves, wind and seagulls was a truly eye opening experience for me. Captain Iris was absolutely enchanting with the stories of Saint Michaels and her beloved Selina II. The cruise was intimate with only 2 other couples and was an experience I will long remember.

Captain Iris runs a fabulous operation out of St. Michaels. This was our first time visiting the town and this was such a great way to experience St. Michaels and the Chesapeake. The Sunset Champagne cruise was fun and intimate as only 6 people maximum. The two other couples we met were so sweet. Sail Selina II is a must do in St. Michaels!

Why Sail Selina II?

Rated #1 on tripadvisor.

When looking for things to do in St Michaels MD, o ur reviews tell the story! Limited to just six guests, Sail Selina II is ranked the #1 Maryland sail boat tour in St. Michaels and has been for 18 years running.

Everything Is Included

Sit back and relax. Want a drink? We’ve got it! Cold beer, red & white wines, Champagne, and soda are available for sale on all our Maryland sailboat rides and are included on our evening charters.

Over 96 Years of Experience

Sail Selina’s top-notch skippers have a combined sailing history of 90+ years, and her friendly crew has a combined sailing history of 30+ years. We all love to sail and we love taking people for sailboat rides!

Spacious & Beautiful Boat

All our relaxing sailing boat charters are in a gorgeous setting. Sail Selina II was built as a gentleman’s yacht in the Gatsby era and is finished in freshly varnished mahogany and brightly polished bronze. Her spacious cockpit is the perfect setting for a Maryland sail on the ultimate charter boat in St Michaels, MD. Join us for a sailing charter boat tour and unwind with an authentic taste of the history of sail.

The Best Captains

Our St Michels boat tour captains are known for their storytelling skills and offer a boat trip balanced with some touring, some sailing, and some time to simply relax, unwind and kick back. When sailing on the Chesapeake in St Michaels, choose from a basic sailboat ride, or opt for a specialty outing like a local craft brew beer tasting cruise or a sunset champagne charter.

Sailing Charters, Lessons & Captain Services in Annapolis, MD & Abroad

We Have a Chronic Sailing Condition

sail with us and you will too!

Annapolis Sailing Charters.

Sail the Chesapeake Bay on your own private yacht. Select a trip from our popular itineraries below, see more sailing trips in the Chesapeake Bay or contact us to customize an itinerary just for you.

Annapolis Sunset Cruise

Catch the gorgeous Chesapeake Bay sunset aboard a luxury catamaran. Perfect for a romantic evening, cocktails with friends or a way to end a day exploring Annapolis.

Mid-Week “3 Hour Tour”

“Just sit right back and…” feel the wind in your hair, go for a swim or just enjoy the views. Great for office outings and happy hour hangs.

Celebrate Your Special Event

Birthdays, anniversaries, bachelorette parties and other occasions are more fun on your own private yacht! We’ll tailor a cruise for your special day.

Chesapeake Overnight Sail

Get away for a night (or 2) and enjoy adventures on the water, excursions into nearby towns, sunset cocktails and sleeping under the stars.

Annapolis Sailing Lessons

ASA certified instructor, Captain Shawn Owen helps students of all skill levels become confident and safe sailors. With decades of experience teaching snowboarding and music, Shawn has a laid back, positive attitude and a passion for sailing and seamanship that will be contagious when you sail with us.

If you’ve never sailed before and are interested in trying it out to see what all the fuss is about, this class may be the perfect way to give it a shot.

Intro to Sailing

Interested in one on one training? Or maybe you want to get you and your crew up to speed before an upcoming charter? We can customize private instruction for up to 4 people for an extremely competitive rate.

Private Sailing Instruction

New boat owner needing insurance checkout or just looking to brush up skills on your own boat? We offer instruction and certifications aboard your boat to maximize benefit and personal knowledge of your vessel.

Learn on your Boat

The American Sailing Association is a national and global leader in sailing education and bareboat chartering certifications. We offer ASA Courses 101-106, as well as the 114 catamaran certification. If bareboat chartering is something you see in your future, then this could be your best avenue to achieve the necessary skills and qualifications required to handle your own charter vessel.

ASA Courses

Learn To Sail

Browse our charter fleet.

This modern marvel stands out with sleek lines and a spacious deck layout, ideal for leisurely cruises or adventurous voyages.

American Honey

This state-of-the-art catamaran seamlessly combines performance, comfort, and elegance to provide an unforgettable chartering adventure.

Dos Milagros

Experience the ultimate luxury sailing adventure on the stunning Chesapeake Bay aboard the exquisite 2017 Beneteau Oceanis 45, a true gem in the world of yacht chartering.

Let us plan your customized “escape” on this well appointed catamaran sailing the Chesapeake Bay out of Annapolis, MD

A magnificent vessel that seamlessly blends luxury, performance, and comfort on the open seas.

This sleek and modern vessel feature 3 cabins, each equipped with its own private en-suite bathroom. Expansive deck with plenty of seating and lounging areas.

JEHM of the Sea

A versatile and comfortable sailboat designed for cruising, well-suited for exploring the waters of the Chesapeake Bay.

Stay in the Loop

I want to know about new classes, specials, events and offers from Chronic Sailing.

Life is Just Better on a Boat

sail with us!

Sailing changed my life for the better in nearly every way. It makes me more present, more thoughtful, more focused, healthier, happier, just better as a person in most every way. I would be honored to help share it with you and then watch it become a part of your life.

Keep it chronic.

- Captain Shawn

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	Admiral of the Bay Nautical Event Designers

, or large schooners. Your Nautical Event Designers for all your corporate needs, cocktail or dinner cruises, Chesapeake Bay crab feasts, and unique formal dining occassions. We also specialize in nautical engagement, wedding and anniversary parties too! We also accept bitcoins through to enable easy transaction.

Sailing Season is Here. Join Us for a Sail!

Rates and Schedule

FOR 2-HOUR SAILS
	Weekday Daytime	Sunday & Sunset	Saturday & Holidays
All Guests	$62.00 (Ticket) + $3.75 (Booking Fee) + $6.20 (A&A Tax)	$65.00 (Ticket) + $3.75 (Booking Fee) + $6.50 (A&A Tax)	$69.00 (Ticket) + $3.75 (Booking Fee) + $6.90 (A&A Tax)

Includes a complimentary soda or water.

Everyone has loved having more room, so we are staying at just 30 people per cruise (instead of 48).

Tickets go on sale 6 days prior to the date you want to sail.

2024 Public Sailing Schedule

April 13 – april 23, seven days a week.

12:30 pm – 2:30 pm 3:00 pm – 5:00 pm 5:30 pm – 7:30 pm (Sunset Sail) * * Friday, Saturday & Sunday only

April 24 – May 10

12:30 pm – 2:30 pm 3:00 pm – 5:00 pm 5:30 pm – 7:30 pm (Sunset Sail)

May 11 – August 25

11:00 am – 1:00 pm 1:30 pm – 3:30 pm 4:00 pm – 6:00 pm 6:30 pm – 8:30 pm (Sunset Sail)

August 26 – September 22

10:00 am – 12:00 pm (Saturday & Sunday Only) 12:30 pm – 2:30 pm 3:00 pm – 5:00 pm 5:30 pm – 7:30 pm (Sunset Sail)

September 23 – 29

11:00 am – 1:00 pm 1:30 pm – 3:30 pm 4:00 pm – 6:00 pm

September 30 – October 16

No 2 hour public sails due to US Boat Shows Private Charters are available

October 10 – October 14 we will be sailing from the US Sailboat Show

October 17 – October 31

Once tickets are purchased, there are no refunds or exchanges.

We sail rain or shine, unless the captain cancels the cruise due to unsafe conditions. We offer complimentary rain ponchos in case of rain.

Please Remember:

• Only soft-soled shoes are allowed aboard.
• All departures are from Pusser’s Caribbean Grille at the Annapolis Waterfront Hotel across from the City Dock (unless otherwise noted) . Rates and schedules are subject to change without notice. Our schedule may vary due to weather, special events, and group charters.
• Tickets go on sale six days prior to the date you want to sail.   Please call our business office at 410-263-1981.
• Up-to-date schedule information is available by clicking here or calling (410) 263-7837.

Questions???

Please visit our frequently asked questions page.

"Seriously Fun"

Learn to Sail the Annapolis Way

Adult Sailing Lessons

Youth Sailing Lessons

Join KeelBoat Club

Rent a Sailboat

Evening Sailboat Charters

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Which course is right for me.

I want to be able to operate a vessel I already own or intend to buy.

I intend on renting or chartering sailboats in the future.

I want to explore the art of sailing and am looking for a great experience.

I'm looking to learn at my own pace with personalized private instruction.

Sailing is an Experience to be Enjoyed Over a Lifetime

We provide a community at the Annapolis Sailing School for your ongoing growth and enjoyment. We offer day sailboat rentals, adult sailing, KeelBoat Club Membership, KidShip sailing, powerboat lessons, and events at our beautiful location on Bembe Beach.

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Annapolis Sample Itinerary

The Waypoints Annapolis base is in the heart of Annapolis right in the middle of the sailing capital of the world. The Chesapeake Bay, at about 200 miles long, is the largest estuary in the United States. There are coves and inlets all along the shoreline, small quaint towns to explore, and plenty of places to anchor or dock with history all around you as you explore national landmarks.  

Your destinations on the Chesapeake Bay are boundless. Make sure to allow time to visit downtown Annapolis at the beginning or end of your charter. Here you will find Main St. and small side streets loaded with shops, restaurants, galleries, and the Market House. And if time allows, take a stroll through the Naval Academy. Whatever you choose, you cannot go wrong in this historic town. 

Sailing Itineraries are helpful when planning your charter. You can choose the North or the South route. North takes you to historic Baltimore Harbor with nice quiet anchorages along the way. Sailing the South route will take you to places such as the legendary St. Michaels and the historical landmarks in Oxford and Cambridge. 

So many destinations on the Bay to explore makes Annapolis a great choice for your charter vacation.

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Annapolis Fall Charter Special. Get One Night FREE!*

410-956-9729

South River Boat Rentals

Welcome to south river boat rentals, boat rentals and charters on the chesapeake bay, family, social & corporate outings.

30+ Years Serving Chesapeake Bay Boaters

We had a FANTASTIC time on the Bennington boat. Our Captain Max was a blast! He found multiple spots for us to hang out in the water, and even drove us around tubing! 10/10 recommend for your Annapolis boat rental!

WATER SPORTS AND MORE

We offer water sports – tubing, skiing, wakeboarding, and kneeboarding.

Water Sports on the Chesapeake Bay bring all of your family and friends together.  Whether you enjoy water skiing, wakeboarding, tubing, or knee boarding, we have the water sports for you on the Chesapeake Bay.

Our Rental Fleet

19' Hurricane (S)

1/2 day: $550 | full day: $900, 6 max / wt limit: 1410 lbs.

21' Kencraft

6 max / wt limit: 1250 lbs.

26' Bennington Pontoon

1/2 day: $800 | full day: $1400, 12 max/wt limit 2200 lbs..

26' Chaparral Sunesta

10 max/wt limit 2600 lbs..

26' Crest Tritoon

12 max/ wt limit 2400 lbs..

26' Everglades

1/2 day: $950 | full day: $1700, 10 max including our captain.

SEE PRICING DETAILS

30 max passengers / includes captain.

50' LRC Trawler

12 max passengers / includes captain.

Our Customers Love Us!

 Just Google "South River Boat Rentals" to see all the positive reviews we have earned throughout the years. Customer service and ensuring you have an excellent day on the water is our top priority.

We used South River boat rentals this past weekend for a bachelorette party and had the absolute best time. Special thanks to Captain Chris and the rest of the crew who were all kind, courteous, and informative. Definitely will be returning! - Gabby Cooper

Amazing day on the pontoon boat with our extended family. Graham was a WONDERFUL captain and host. He took us to a quiet area to swim, dragged all 4 kids in the tube, and slowed the boat so we could look at wildlife up close. Worth every penny! Highly recommend requesting Graham as your captain. - Meredith Bove

Thank you for a memorable experience. Would recommend this place to everyone. Can’t wait to make another reservation in the future. A big thank you to Nancy for your amazing customer service and friendly personality!! - Nicole Wilkinson

Thank you for an amazing time. We rented the 26' Chaparral for a day of cruising and tubing. We could not be more grateful. The boat ran perfectly and the staff was king, courteous and accommodating. We will return! - Garrick Muench

Had a great experience with them. I even had to reschedule for a later date and they were able to accommodate! Would definitely recommend the 50' Trawler! - Kourtney Ramseur

Such an amazing company to work with!!! From scheduling, to weather related rescheduling, the captain, and the overall boat condition and experience - I cannot say enough good things about South River Boat Rentals! Definitely will return! - Tara Klimovitz

The boat was ready and waiting for us; the service was good from booking to returning the boat. South River made it an easy and enjoyable experience. - Judy Graham

So much fun renting a boat for the day. Our Captain Wayne was awesome and took us wherever we wanted to go. He gave suggestions based on weather/water conditions/our ideas of what we wanted to do. It was really a great day! - Sarah Edwards

Outstanding Labor Day out on the water thanks to South River Boat Rentals! Best prices in the area, great vessel, easy to use, a lot of fun for our family! - Mark Fratto

The staff was awesome and super hospitable. They walked us through everything and made sure we felt comfortable on the boat. Boat was in great condition too! - Dylan Stoskus

We had a wonderful experience with South River Boat Rental! The boat was in perfect condition, very clean, and the staff was a pleasure to work with. Would highly recommend! - Liz Gillette

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Start with A Free Quote For Your Next Adventure. You can also book online by going here: Book Online

For questions, information and details about your rental/charter please call: 410-956-9729.