Cruise Annapolis

Cruise Annapolis, a Waypoints Destination, is a boutique charter company in the heart of Annapolis offering luxury bareboat charters, crewed yacht charters, & ASA sailing instruction on the Chesapeake Bay. Our world-class fleet consists of new model Fountaine Pajot sailing catamarans and motor yachts, and Jeanneau sailing monohulls and powerboats. 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, we're here to help you make the most out of your excursion. Additionally, if you love chartering so much that you'd like to own your own vessel, we have yachts available for ownership! Contact your Cruise Annapolis Charter Concierge to learn how it is possible to offset 80-100% of new yacht costs with tax advantages and income.