Cruise Annapolis offers luxury bareboat and crewed yacht charters, sunset cruises, and day sails on the Chesapeake Bay onboard one of our world class Jeanneau monohulls or Fountaine-Pajot catamarans. We are in the heart of Eastport in Annapolis. Our fleet consists of new and nearly new yachts. All are well equipped and meticulously maintained. We provide itinerary planning, provisioning and catering services, and more. We're here to handle the details of your sailing excursion so you don't have to. Wanting to venture outside the Bay? We have affiliate base locations in Florida, the Bahamas, Belize, and the BVI/USVIs . We can help you plan a sailing vacation anywhere in the world. We offer ASA instruction. Go out at any time, for any length of time, to learn with a certified instructional captain. Call us today for our most current promotions and offerings.