Cruise Annapolis

Charter Company

Cruise  Annapolis
cruise annapolis
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About Cruise Annapolis

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!

Boats & Rates

Boat Lengths: 38'-50' Feet
Boat Types: Sailing and Power Catamarans and Monohulls
Charter Types: Captained, Bareboat, and ASA Sailing Instruction

Charter Destinations

  • Chesapeake Bay

Contact Us

Cruise Annapolis
222 Severn Ave
Suite 36, Bldg 15
Annapolis, Maryland 21403

Phone: (443) 203.4112