Dating in Annapolis
In shortAnnapolis is the state capital and a sailing town, with brick streets running down to City Dock. It feels small and walkable. Being near the water sets an easy, relaxed tone for a date.
A first date idea
The Annapolis Spring Sailboat Show
The Annapolis Spring Sailboat Show is held at City Dock, and the 2027 show runs from 23 to 25 April. You can walk the docks and look over the boats together. Check tickets and times on the show's site nearer the date.
Source: Annapolis Boat Shows: Annapolis Spring Sailboat Show, checked 9 November 2026
Wander the docks together at the spring sailboat show.
For more ideas, read boats, beaches and the Bay: dating around the Chesapeake or dating between Baltimore and the DC suburbs.
