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. Annapolis is one of the best sailing destinations on the east coast, and makes it the perfect place for you to begin your exploration of the Chesapeake Bay.

At Annapolis Bay Charters, we combine a great fleet of well-maintained sailboats, a service-oriented staff with over twenty-five years experience, and a yacht charter location that makes it easy to visit some of the Chesapeake Bay's best spots. Our friendly staff will help you select just the right sailboat for your needs and experience. To make your voyage as enjoyable as possible, we offer many extras such as itinerary planning, instruction, 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 charter boats in Annapolis to provide our clients with unique, on-the-water experiences.

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, and many other special events.
Sail through our website and let us know how we can make your cruise a breeze!