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You'll find a space on the street if you try. It's really not that hard. There is the big garage at the Ben and Jerry's and then there is a lot down in by 'Ego Alley' / City Dock. I also like this little side street near the new pedestrian / visitor entrance to the Academy (it's one way and not trafficked much so you can get lucky).
See the Academy. You will need a photo ID to enter but go in, check out the Chapel, and go into Bancroft Hall (the main dorm) and you can walk up the stairs to the main ballroom (where they have dances and the Annapolis Peace Conference was held). There is a museum at the academy but I think it is under repair. If it is open GO TO THE BASEMENT and see an incredible collection of model ships. Some amazing works of art.
In the city walk up and down the main street, around church circle and the Capitol building. There is a quirky side street called Maryland Avenue that most folks don't know about but which has some fun stores.
If you want to drive, head down to Bay Ridge (go over the Eastport drawbridge from city dock, turn right the second street after the Mercedes dealer and follow that road for about a few miles until Forrest Drive, turn left and follow that a few miles until it dead ends in Bay Ridge, some beautiful houses on the water. Look it up on google maps to get a clear picture.
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