Annapolis Spring Sailboat Show

Set against the stunning backdrop of Annapolis City Dock, the Annapolis Sailboat Show is one of the most celebrated nautical events in North America. Running Thursday through Sunday, October 15–18, 2026, this iconic in-water exhibition transforms the historic Chesapeake Bay waterfront into a floating showcase of the world's finest sailing vessels. Whether you're a seasoned sailor or simply captivated by the elegance of sail, this four-day festival offers an unparalleled opportunity to step aboard and explore hundreds of magnificent boats up close. Visitors can climb aboard a vast fleet of monohulls, catamarans, and performance sailboats, speaking directly with manufacturers, designers, and expert crews. The docks come alive with product demonstrations, rigging seminars, and navigation workshops, making it as educational as it is exhilarating. Vendors and marine gear exhibitors line the waterfront, offering the latest in sailing technology, apparel, and accessories — a true paradise for boating enthusiasts of every level. The atmosphere at Annapolis City Dock is nothing short of magical during show weekend. The smell of salt air, the gentle clinking of rigging, and the golden autumn light reflecting off the water create a sensory experience unlike any other festival. Whether you're planning your next blue-water voyage, shopping for your dream vessel, or simply soaking in the vibrant maritime culture of Annapolis, the Sailboat Show is an unmissable celebration of the sea.