Overview Annapolis Boat Shows runs four boat shows a year on the Chesapeake Bay with the boats afloat for shoppers to climb aboard, and its fall Sailboat Show at Annapolis City Dock began in 1970 as the first in-water sailboat show ever held. The company bills it as the largest in-water sailing show in the world. Spring opens with the Bay Bridge Boat Show at Safe Harbor Narrows Point on Kent Narrows, followed by the Annapolis Spring Sailboat Show, which the company calls the fall show's little sister. In October the Annapolis Powerboat Show and the Annapolis Sailboat Show take City Dock on back-to-back weekends. Across the four, the company counts about 1,200 exhibitors and 800 boats a year. On site City Dock, the downtown harbor inlet locals call Ego Alley, fills with boats moored in the water. Most can be boarded. Shoreside tents sell gear, electronics, foul-weather clothing and charters. The 2026 Powerboat Show lined up more than 400 boats, trawlers and downeast boats through center consoles, pontoons and inflatables, over two miles placed bow to stern. The 2026 Sailboat Show counted more than 500 exhibitors, premiered the Knysna 550 catamaran and the Sun Odyssey 455, and added four bars, one of them a floating No Wake Zone bar. Cruisers University runs the week of the fall show with more than 80 classes. The 2026 Bay Bridge show put more than 250 boats and 130 marine vendors at Grasonville, with a demo dock for sea trials. Audience The shows exist to put buyers and sellers on the same dock, and dealers bring boats to be boarded, compared and test-run. Visitors come from all 50 states, four Canadian provinces and more than 30 countries, per the company's 2026 prospectus, and the Spring Sailboat Show draws sailors from across the Mid-Atlantic at the start of their season. Brand presence Top sponsorships run on three-year commitments. A presenting sponsor's name goes on all four shows, with a 20-foot scrim on the fence line, a banner on the main gate trussing and reusable bags handed out at the gates. An official automobile sponsor and an official truck sponsor each get vehicle display space and test drives at the shows. The three tiers below take booth space and fence scrims, a gate sponsor owns the fall entrances, and smaller buys brand the water refill stations or the bags and bottles staff hand out. The shows' own marketing runs TV spots in the DC, Baltimore and Philadelphia markets, regional radio and podcast promotion through SXM Media.