Boat Baltimore: Private Charters & Local Charm on the Chesapeake

Boat Baltimore is a locally owned and operated sailing charter company offering unforgettable experiences on the water in the heart of Charm City. Whether you're a local looking to see your city from a new perspective or a visitor seeking a one-of-a-kind adventure, our private charters offer the perfect escape.

Step aboard our 45-foot sailboat for a private cruise through Baltimore’s historic harbor and beyond. From peaceful morning sails to golden hour sunset cruises, every trip is tailored for small groups of up to six guests. We specialize in elopement and micro-wedding packages, romantic proposals, photo shoots, and special events like fireworks nights and Pride celebrations.

Founded by U.S. Army veteran Captain Bobby and his wife Alicia, Boat Baltimore combines maritime tradition with local passion. Together, they bring warmth, humor, and hospitality to every charter—creating experiences that feel less like a tour and more like sailing with friends. They also partner with community organizations and proudly promote the best of Baltimore through their Sail Local initiative.

Come for the views, stay for the vibe—and sail away with a new love for Baltimore.