Annapolis Spring Boat Show 2024 Tickets. $18 in advance at annapolisboatshows.com, $20 at the gate. Attendees can board and inspect dozens of new and brokerage sailboats at the spring sailboat show, which is one of the best things to do on the chesapeake bay in annapolis.

To 6 p.m., sunday 10 a.m. Sailors from around the globe gather in beautiful downtown annapolis every october for the annapolis sailboat show.