The Chesapeake Bay is well-known as an outstanding waterway for sailboat cruising. Protected waters, great anchorages, gorgeous natural scenery, unique towns and villages, and a forgiving bottom make the Chesapeake an excellent choice for sailors, novice and expert alike. Historic Annapolis, the crown jewel of the Mid-Atlantic, is the best sailing destination on the East Coast, and is the perfect place for you to begin your exploration of the Chesapeake Bay.

At Annapolis Bay Charters, we are more than your everyday boat rental operation. We combine an impressive fleet of well-maintained sailboats and powerboats, a service-oriented staff with over thirty years experience, and a yacht charter location that makes it easy to visit some of the Chesapeake Bay's hidden gems. Our friendly staff will help you select just the right boat for your next cruising vacation. To make your voyage as enjoyable as possible, we offer many extras such as itinerary planning, sailing instruction with our new NauticEd Sailing School, provisioning, captain and crew services, and even airport pick up.

Have a large group of people to entertain? Looking for a group charter boat? We can help with that as well. We work with the finest in the Annapolis area to provide our clients with unique, on-the-water experiences. event charter yachts

We can get you on board a fast, fun wooden schooner, an elegant motor yacht, or an exciting fishing boat. These charter boats make great venues for corporate outings, family reunions, weddings, famous Maryland crab feast, and many other special events.

Sail through our website and let us know how we can make your cruise a breeze!

We now have a Neel 45 Trimaran called "V"! Check it out!

Annapolis Bay Charter News
Neel 45 Trimaran Added to Our Fleet!

, the most innovative “learn to sail” training program in the USA. Sign up now for Spring Classes!

Active Yacht Ownership Program!

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