Boat Baltimore offers private sailing charters in the heart of Charm City. Explore historic harbors, toast the sunset, or elope at sea aboard a 45-foot sailboat—hosted by locals who love Baltimore as much as they love sailing.

Experience Smith Island’s communities, traditions, environment and culture on our customized tours. Guided by local islanders onboard a classic deadrise workboat, our tours take you to the heart of the island’s beautiful, unforgettable landscapes and clo

Sail away on two, identical 74-foot, classic wooden schooners on the Chesapeake Bay. Try a two -hour public cruise or private event that sails past the USNA and then into the Bay. Raise the sails, steer the boat or sit back and relax.