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. We are finalizing our 2022 calendar - check back soon for more cruising events! Have a great idea for a place to cruise or a favorite place you want to share? Click here to host a cruise: Host a Cruise