Annapolis Sailboat Show October 2025 Dates. The annapolis sailboats show runs october 10 through october 14, at the city docks in downtown annapolis. In october, boaters from around the globe gather on miles of docks in historic annapolis for the powerboat and sailboat shows.
The powerboat show displays more than 300 boats. The following is a list of boats that will be on display at the 2025 annapolis sailboat show.