Annapolis Boat Show – Sail City Dock, Annapolis, MD October 12 - 15, 2023 09:00 - 18:00 Add to calendar Sailors from around the globe gather in beautiful downtown Annapolis every October for the Annapolis Sailboat Show. This annual celebration of sailing features floating docks lined with sailboats from manufacturers from around the world. Multihulls, monohulls, cruisers, racers, sailing dinghies and more. Show tents line the shoreline, stocked with the latest in nautical gear and accessories, electronics, communication equipment, sails, rigging, education, charter companies, clubs and more. Seasoned and novice sailors alike are invited to expand their horizons and connect with fellow sailors during this internationally acclaimed show. Stay tuned following our Spring Shows for updates on the Annapolis Sailboat Show.