Seems to me that up the ICW and around the Delmarva penisula would be a good fit.
Specifically, I mean up the ICW to the Chesapeake Bay, up the Bay to its head where a canal connects it to the Delaware Bay, and then down the Atlantic to complete the loop.
You didn't say anything about the size of your boat, so that makes details impossible. Get sailing guides to the areas and read. The Chesapeake is loaded with crowded sailing centers and tiny fishing harbors - what ever is your taste, but by all means taste all of these. Visit the islands (Tangier/Smith). Visit Annapolis. Visit the Virgina Coast Reserve (Chincoteague and the islands to the south).
IMHO, unless you want to sail VERY hard, going north of Cape May on your time line will take the fun out of it. From Cape May to the Long Island Sound is just a grind.
Google "circumnavigate delmarva" and you will find some stuff on the net. There is some stuff on my blog as well.
(when asked how he reached the starting holds on a difficult rock climbing problem that clearly favored taller climbers - he was perhaps 5'5")
"Well, I just climb up to them."
by Joe Brown, English rock climber
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Last edited by pdqaltair; 03-15-2009 at 10:28 AM.
Reason: add photo