The Naval Academy has a beautiful campus and is located right in the heart of downtown Annapolis. You can go on a guided tour or peruse the grounds yourself. Just make sure to bring a government issued ID with you for entrance.
This is a really great cute tearoom and restaurant (in the oldest continuously open establishment in the state - George Washington used to frequent this place). Inside is an English tearoom, and out back they have a fun courtyard bar with more casual fare and a bar.
This is as "sailor's bar" as it gets, with a fun atmosphere and casual good seafood. Situated right across spa creek bridge in the Eastport neighborhood, this fun spot is a short walk across the bridge.
This is a great intimate spot for killer seafood in Eastport, a bit more upscale than Boatyard, but still reasonable.
This is a bit of a hidden gem outside the downtown area of Annapolis, but a MUST for a traditional Maryland crab feast! You will need to drive here though if you're staying downtown.
This is where Chris proposed to Lexi! A very scenic neighborhood about a 10 minute drive from downtown with great views for a waterside walk or run.