…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, Annapolis sailing instruction with our new NauticEd Sailing School, provisioning, captain and crew services.