Waypoints® Annapolis, formally known as Cruise Annapolis, is a boutique charter company in the heart of Annapolis. We offer luxury bareboat charters, crewed yacht charters, and ASA sailing instruction on the Chesapeake Bay with a world-class fleet of new Fountaine Pajot catamarans, Dufour monohulls, and Jeanneau monohulls. All of our yachts are well equipped, privately owned, and meticulously maintained. Find serenity in quiet protected anchorages or stay in lively marinas while you explore the quaint towns of St. Michaels, Rock Hall, Baltimore, Solomons Island, Oxford & Tilghman Island. Whether you are looking for a short sailing getaway or a longer trip to explore the historic locations on the Bay, we're here to help you make the most out of your excursion including developing an itinerary for your trip.

Profile: Captain

Social links