If you get hot doing the walking around thing, there is a public pool in Truxtun Park. If DC requires a swim diaper, they are pretty strict about kids wearing "ecology suits" - which they sell for $6 - over the swim diaper to keep the pool cleaner.
Anyway it is in a nice spot near the head of Spa Creek (there is a boat ramp) and there is a playground on the other side of the parking lot.
http://www.annapolis.gov/Government/Departments/Recreation/Parks/SwimmingPool.aspx
When I go to Annapolis it's usually by boat so the priorities are fresh ice, cold beer and a good meal. The BoatYard is nice and casual and walking distance from East Port boat marinas...we usually hit the Middleton Tavern for oyster shooters, and they have a kid's menu, it's right at the center harbor area.