All depends...
on what you like...sailing, history, food, etc? You are right, this isn't the best time of year as most things are closed and/or frozen. Here are a few ideas:1. Ego Alley: This is the main harbor (really a canal) downtown, there are quite a few boats docked there for the winter. In warmer weather, this little canal would be crammed with dinghys, boats, ducks and anything else imaginable. Last week all I saw were ducks playing on the ice. 2. Fawcetts is the local chandlery on the waterfront. Something like mecca for the sailor. New owners have just spruced the place up. Stop by, tell them you are visiting, they will get you going. There are also lots of free local maps, mags and such there.3. Phillips Seafood overlooks ego alley. OK food for what it is, great views.4. Dockhouse Coffee (behind the Market House which is now closed...) best little coffee shop downtown.5. Naval Academy is to the north of Ego Alley: beautiful place, great views and nice tours of a few of the historic bldgs there. Be sure to take ID or they won't let you in.6. Eastport is just accross the bridge. Lots of boat yards, upscale restaurants, etc. When you cross the bridge, imagine both sides of it full of boats moored to the city moorings. It's a beautiful site.7. Boatyard Grill in Eastport: currently the sailor's hang-out in Annapolis. (Replaced an older bar on the waterfront that is no more.) Good food, lots of drink and talk.8. There are several historic houses open to the public (Paca House for one). There are tours and guides if that's your thing.9. The 3 largest boatyards are off on Back Creek and not accessible by foot. (Bert Jabins, Port Annapolis and Annapolis Landing.) If you are a marina rat (like me) they are a great place to ride and visit. Also, some good views of the bay.Post more specifics on what you are interested in or email me at dcdon@hotmail.com.Beautiful place, almost heaven in warm weather.