Annapolis Bay Charters, Inc.

The oldest, and most respected Charter Company on the Chesapeake Bay. The oldest, and most respected charter company on the Chesapeake Bay.

Operating as usual

A day in the life of a BVI skipper | Dream Yacht Charter 09/01/2019

A day in the life of a BVI skipper | Dream Yacht Charter

"Pour a drink, take a dip and soak up the sun. Let the day take you where it may, and we will take care of the rest", Lisa Rolland. Read about a day in the life of a BVI skippper, and how the movement has inspired Lisa to become a great captain for DYC. ⛵

A day in the life of a BVI skipper | Dream Yacht Charter What does it take to be one of our skippers? Meet Lisa Rolland, one of our highly experienced female skippers in the BVI and find out...

Photos from Annapolis Bay Charters, Inc.'s post 07/23/2019

Congratulations to our Dream Yacht Charter Annapolis team for winning in the 2019 Screwpile Regatta. 1st in class and 1st overall winner this past weekend. Well Done!


Who is going to be sailing on the Chesapeake this weekend?


Dream Yacht Charter in Annapolis, MD is looking for charter skippers for this season. There are a few charters starting next week that are in need of skippers. If anyone is interested please let us know and we will provide details.

Annapolis Bay Charters, Inc. updated their phone number. 06/24/2019

Annapolis Bay Charters, Inc. updated their phone number.

Annapolis Bay Charters, Inc. updated their phone number.

Photos from Annapolis Bay Charters, Inc.'s post 06/21/2019

Champagne toasts all around. Our sales broker Brad toasts Scott the new owner of a beautiful Dufour 56. She is available for charter now at our Annapolis base and she moves to the BVI in November. Congratulations Scott and to you our customers who will be able to sail this incredible boat.

Dufour 390 and 430 Sea Trials 05/07/2019

Dufour 390 and 430 Sea Trials


We are hosting a free open house for Dufour Yachts on Saturday June 23rd from 10 AM to 4 PM! Please make plans to join us there for special pricing on in-stock models, and if you have ever wanted to know more about how charter ownership works and how you can sail away one of the many Dufour models we have in stock: 350, 360, 382, 412, 460 and 520 are all available now and this summer! Register here:


The broker on duty today is Bailey. She would love to meet you, tell you about the joys of chartering, and show you our boats for sale :) 01/29/2018

Fleet of Boats, Sailboats and Catamarans for Rent - Annapolis - Dream Yacht Charter

Receive an early booking discount of 10% when you book an Annapolis charter before the end of day on January 31st! Returning customers will also receive an extra 5% off. Discover a large fleet of boats, sailboats and catamarans for rent - Annapolis - Dream Yacht Charter 09/19/2017

Dufour Yachts Preview Event | Dream Yacht Sales

Please join us for this great opportunity to beat the Annapolis boat show crowds to preview the new Dufour, Bali and select Lagoon models all together at our base. Food, drink and fun talking to our team! RSVP to reserve your spot today!


Dream Yacht Charter founder, Loic Bonnet, says: We are deeply saddened by the reports of Hurricane Irma's impact. We have staff all around the Caribbean and our thoughts are with our people and all those affected by this devastating storm. Strong, resilient nations make up this special part of the world and we'll be supporting their recovery. 09/06/2017

The Chesapeake Bay: Hidden Wonders | Blue Water Sailing

Have you sailed to any of these great placed before? There is still some time left in the summer to do it!


We have some leftover deals from 4th of July for you all! Book & sail a two-day minimum weekend - get a FREE sleep aboard the night prior OR Book & sail four-day minimum charter - get a FREE day sailing. Offer ends at 5PM Friday July 14th. 06/27/2017

4th of July on the Chesapeake | Annapolis Bay Charters

Looking to spend your 4th of July on the Chesapeake? We are running a special celebrating 241 years of independence; $241 off new charter bookings between June 30th and July 4th! View some of the best 4th of July happenings on our latest blog post: It is almost that time of year again. Time to celebrate America with a day filled with boating, fireworks, BBQs, red, white, and blue. Everyone has their different traditions for the 4th of July. Whether you go to the beach with your friends, or stay for the family BBQ; everyone’s night usually ends... 05/19/2017

Annapolis Memorial Day Happenings | Annapolis Bay Charters

With Memorial Day weekend approaching, we decided to team up with Dream Yacht Charter and compile a short list of great events on the bay for you to experience! As Memorial Day approaches through this coming weekend, you are probably wondering what kind of events in Annapolis you should attend. 05/09/2017

Sailing in Annapolis – Choose your Chesapeake Bay Charter

Our fleet is growing! Plan your summer charter on the now! 04/24/2017

The Wildlife of Chesapeake Bay | Annapolis Bay Charters

Diverse and dynamic, varied and vivid, engaging and enjoyable; this is the wonderful wildlife of the Chesapeake Bay. Diverse and dynamic, varied and vivid, engaging and enjoyable; the wonderful wildlife of Chesapeake Bay, & experiencing it by sailboat.


Annapolis Spring Sailboat Show 2017

Annapolis Spring Sailboat Show is coming up fast! Remember to chat with us and Dream Yacht Sales at the big event!

April 28-30, 2017 04/13/2017

Chesapeake Bay Maritime Museum - Dream Yacht Charter

The Chesapeake Bay Maritime Museum has been called a “national treasure” by some on TripAdvisor, and we couldn’t agree more with that statement. The Chesapeake Bay Maritime Museum has been called a "national treasure" by some on TripAdvisor and we couldn't agree more with that statement. 04/11/2017

Chartering the Chesapeake

Interested in chartering the Chesapeake? Here is a great little article from SpinSheet Magazine to get you started! Ideas and inspiration for chartering a sailboat on the Chesapeake. By Beth Crabtree


Anyone going to be joining us at the Annapolis Boat Shows Spring Sailboat Show? We are still accepting boats into our charter fleet and we would love to see you there at our booth with Dream Yacht Charter and Dream Yacht Sales!

Dream Yacht Sales is excited to be showing off three of the most popular Dufour Yachts Grand Large cruising models at the Annapolis Spring Boat Show. April 28-30th.

Any one of these models would make a perfect boat for charter or personal use, and Dream Yacht Sales has charter management opportunities available to make ownership easy for you.
This year we will have the 382, 460 and 512 on display. All three of these models combine the most comfortable shoreside amenities with offshore capable sailing.
The Dufour 382 was Cruising World Magazine choice for Best Midsize Cruiser in 2016. This boat of nearly 37 feet LOA feels very spacious on the inside like a bigger boat, but while sailing, it is as responsive and easy to sail as many smaller boats. The interior is available in various 2 and 3 cabin layouts.
The Dufour 460 is ready to take racing around the buoys, coastal cruising, day sailing or offshore. This boat has also been designed to “heighten the social side of sailing” according to a recent review in Cruising World Magazine. This boat has a deck layout that allows for easy sailing but it is also optimized for entertaining, with unique features such as an outdoor galley option.
The Dufour 512 is the evolution of the popular Dufour 500 which is a standout in the 50 foot class and a Cruising World 2014 boat of the year winner. The new 512 took owner feedback to create a bright and cozy interior with an all new galley design.
Dream Yacht Sales is the official dealer for Dufour in the Chesapeake area.

Come see Dufour at the Annapolis Spring Sailboat Show! 03/20/2017

Charter Destinations: Chesapeake Bay - Sail Magazine

Check out this article from SAIL Magazine on the Chesapeake Bay. Our charters launch for the coming summer season in May. Book now! It’s not every day you can run aground twice in the space of 10 minutes and extract yourself gracefully each time. Chesapeake neophytes, we were feeling our way into the picturesque harbor of Rock Hall, and as we discussed the approach to the marina the boat slowed ever so gently and came to a stop.... 03/05/2017

Sailing in Annapolis – Choose your Chesapeake Bay Charter

Interested in sailing the Chesapeake this coming summer? We just added a few more new boats to our Annapolis fleet! Our well-maintained fleet has boats to suit every need. A divine Annapolis sailing experience is yours in one of our elegant monohulls or catamarans.


Good morning, and Happy Valentines Day!


Happy New Year! Is traveling more part of your ?


Happy Holidays from Annapolis Bay Charters!


Winter is here.


The cold weather got you down? Annapolis Bay Charters reopens May 1st! Start booking your charter today. 12/02/2016

Annapolis Bites: Hot Spots for A Hungry (And Thirsty) Sailor | Annapolis Bay Charters

You arrive in Annapolis with your bags full and your stomaches empty. Where do you eat? So you’ve booked your Annapolis charter experience. You arrive in Annapolis with your bags full and your stomaches empty. You make your way down to the harbor and can’t seem to figure out what you want to eat and drink. Do you go for one of Annapolis famous crab dishes or something else? The downtow...


Timeline Photos


Check out this beautiful photo of downtown Annapolis. Absolutely stunning at dusk! Where are your favorite spots in Annapolis for nightlife? 11/18/2016

Holiday Happenings in Annapolis | Annapolis Bay Charters

Happy Friday! Check out our quick little holiday guide to Annapolis! With Thanksgiving just around the corner and Christmas coming up next month, it’s important you get your dose of holiday cheer between gift shopping and preparing for visiting in-laws. Some people prefer to hit the eggnog while others like to get involved in holiday events. Annapolis may be closed a... 11/15/2016

Annapolis Sailing & Yacht Sales – Annapolis Bay Charters

Discover the magic of Annapolis sailing Annapolis Bay Charters is your first stop on a journey to discover the magic of sailing the Chesapeake Bay. Visit our site to start dreaming – and planning. 11/13/2016

Sailing in Annapolis – Choose your Chesapeake Bay Charter Our well-maintained fleet has boats to suit every need. A divine Annapolis sailing experience is yours in one of our elegant monohulls or catamarans.





7080 Bembe Beach Road #211A
Annapolis, MD

Opening Hours

Monday 8:30am - 5pm
Tuesday 8:30am - 5pm
Wednesday 8:30am - 5pm
Thursday 8:30am - 5pm
Friday 8:30am - 5pm

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