Our favorite place in the whole Virginia area was Krentz Marine
, up the Wycomico river. Quiet, beautiful part of the Chesapeake - very rural. A great restaurant nearby that is open only three evenings a week - Good Eats. Had a great time when we kept Taleisin there. Since we worked on board, we didn't have to have access to a town - so might not work for you.
Lots of luck with your new venture. But don't forget to go out sailing on that boat. It's not just living aboard
that is pleasurable, it's going places with your floating home.