Annapolis Spring Sailboat Show 2025 Tickets. Annapolis, md, is known as the “sailing capitol of the world,” so it only makes sense that the annapolis sailboat show is one of the biggest and best. October in annapolis means boat shows.

2025 edition of annapolis sailboat show will be held at annapolis city dock,. Sailors from around the globe gather in beautiful downtown annapolis every october for the annapolis sailboat show.