We don't do moorings so I can't comment on that except for
Annapolis which has moorings, but here is a list of some of the most popular bay places that we have sailed (except
Baltimore since we live near there, the list is in north to south order):
Baltimore Inner Horbor
Rock Hall - free shuttle around town
Annapolis - Naval Academy tour, lots of restaurants, historic town
Saint Michaels - great maritime museum, historic town, lots of small shops and restaurants
Oxford - very small and only a few restaurants, historic town
Solomons Island - also has a great maritime museum with fossils, lots of restaurants, a bit of a party town