It's not the Chesapeake, but there are some nice towns:
What is the sailing like in the Delaware Bay?
I currently sail in Barnegat Bay, but I am looking for some new scenery, and places to sail to.
Any input appreciated.
Bill
You did not hint at your draft, so I am guessing it is not over 4 1/2'.
Lewes is nice with lots of shops and eateries. The new town dock is nice, right next to a restored light ship. Ft. Miles is worth a visit but too far to walk.
The C&D canal and the upper Chesapeake Bay are not too far at all, for a weekend trip. Get a Chesapeake Bay guide.
Cape May, of course. You can day-anchor rather near nice beaches at Higby - it is deep in close to shore. For the night, there are many marinas in town. You'll need bicycles for the town.
Bowers Beach / Murder Kill is not much, but I've been there. Just a fishing place, really.
The Cohonesay River is a nice wandering path to some good marinas.
Stayed in the Biddwell Creek Marina once. Nice, very quiet, but remote. However, I would go again, in a heartbeat, for the quiet.
I've written a guide book about circumnavigating the Delmarva (see my blog), but to be very honest, the NJ guide suggested is better for the Delaware Bay. My focus is further south and on the needs of smaller boats.
A friend of mine is actually sailing around the Delmarva in an 18' dingy as we speak! I am hoping he gets fair weather. He's a real adventurer.