Annapolis Sailboat Show 2025 Schedule. Seasoned and novice sailors alike are invited to expand their horizons and connect with fellow sailors during this internationally acclaimed show. The 2025 annapolis sailboat show takes place along the banks of city dock in the famous chesapeake bay.

Join the team from seattle yachts annapolis. The annapolis sailboats show runs october 10 through october 14, at the city docks in downtown annapolis.