The Chesapeake Bay is magical. There is nothing better than exploring its waters by sailboat, unless it’s exploring its waters by sailboat with like-minded people. Cruising allows us to explore the quiet anchorages and more active destinations all over the Bay, while building friendships and sailing skills. Knowledge of sailing and seamanship is necessary, but you do not need extensive experience. Everyone has a first cruise. Come join us as we explore the Bay together. Check out our 2024 cruise calendar below. Sign up to join us. Have a great idea for a place to cruise? Click here: Host a Cruise