Baltimore has dockage in the Inner Harbor for about a buck a foot and there are all sorts of things to do and see in the harbor. Annapolis also has moorings at 20 bucks a day or slips at about a buck and a half a foot. Rock Hall has several nice marinas and a town dock. St Michaels has the Harbour Inn-2.50 a foot but a really nice place. Tolchester marina is real nice-don't know their rates.
It all depends on how much traveling you want to do.