Starting from the south and moving clockwise around the Bay; here's mine:
1. From the Portsmouth free town dock at the end of High Street, the Portsmouth Lightship Museum, Comodore Theatre, ferry to Norfolk waterfront.
2. A long trip up the Potomac, but all the sites in DC are available.
3. Cruise up the St. Mary's River to St. Mary's College, Historical St. Mary's City and the replica of the Dove. Summer symphony concerts on the green.
4. Solomons Island,- The Calvert Maritime Museum and their cruising tour to Cove Point Lighthouse.
5. Annapolis,- The old city around Market Square and the Naval Academy
6. Baltimore,- The Inner Harbor, The Pride of Baltimore, The Constellation, Fells Point & Maritime Museum.
7. Havre de Grace, The Decoy Museum, the lighthouse, the historical lock and canal museum at the Susquehanna.
8. Chestertown's historical waterfront and the Sultana
9. St. Michaels and the maritime museum
10. The quaint and culturally isolated villages of Tangier and Smith Islands
There's much more, but these are my top ten. Take care and joy, Aythya crew