Make sure you get a chance to try blue crabs. Cantler's is a good choice. Annapolis is a cool old town. It may be too late in the season but there are usually walking tours that begin near the harbormaster's office, and some of the old homes are open for tours if you are into that sort of thing. The Naval Academy is worth a visit. Its museum has a great collection of old ship builder's models.

Annapolis is beautiful this time of year. my wife and I have been there twice for the boat show. Annapolis is like stepping back in time. there are lots of shops and restaurants to choose from. our favorite is Buddies crabs & ribs. its not easy to find so just ask anybody in town.