I'd head to Pimlico Sound area, Oriental NC, etc, then up to the Chesapeake. As an earlier post noted, lots of unique places to see, and sailing in the fall on the bay is fantastic. You could easily zig zag across the bay, heading north to Annapolis in time for the sailboat show.
I like the Delmarva circumnavigation idea too if you get a good weather window and are comfortable with your boat off shore-- few places to hide if the weather gets bad along that stretch. Just educate yourself as there are strong currents, lots of commercial traffic, etc along the canal and the Delaware river. Sounds like a great time.