Cruise Annapolis, a Waypoints® Destination, is a boutique charter company in the heart of Annapolis. We offer luxury bareboat and crewed yacht charters on the Chesapeake Bay with a world-class fleet of new Jeanneau monohulls and Fountaine Pajot catamarans. All of our yachts are well equipped, privately owned, and meticulously maintained. Whether you are looking for a short sailing getaway or a longer trip to explore the historic locations on the bay, the Chesapeake Bay is among the world’s top cruising and sailing destinations. Choose Cruise Annapolis and discover the Waypoints® difference!