Waypoints Annapolis® offers the best bareboat and crewed yacht charter options along the Atlantic Coast and the Caribbean. From New England, along the mid-Atlantic, around Florida into Key West and the Gulf Coast – even the Bahamas and Virgin Islands – we have charter options available in the Atlantic’s finest sailing waters.
We provide a world-class charter experience, planning out a customized route for your personal sailing adventure. In addition to the Chesapeake, we can provide the same charter experience from a host of destinations, including the Bahamas, Newport, Rhode Island, Ft. Lauderdale, Florida, St. Petersburg, Florida, Key West, Florida and the Virgin Islands.