Here is a very rough chart of the Delmarva circumnavigation that Bruce and I are talking about. The idea circumnavigating the peninsula is not a new one, I read about a man named Washington Tuttle making the trip single-handed in a small catboat. I wrote about "Tut" here.
Bruce and I have tossed around the idea a few times over the years. He brought it up again in our phone conversation yesterday. So here is what we are talking about. We have already sailed the portion marked in red, a combination of the Back to the Islands (spring 2011) and Crabhouse 150 (fall 2009) trips. The next leg (yellow) would be up over the top of the peninsula, though we would probably start the trip somewhere lower on the bay than Rock Hall. Maybe Cambridge or as far south as Rumbly - whatever would give us a nice relaxed seven or eight day trip to Lewes, Delaware (with a side trip to Cape May, New Jersey thrown in).
The last leg would be (in white) from Lewes down the eastern side of the Delmarva, around the southern tip and up the bay to Onancock. The seaside version is very roughly drawn here. Some of it would be inside the barrier islands, some would be outside on the ocean.
The next leg won't be until the fall of 2012, I'll look forward to doing the planning for that. And the final leg would be the year after that. In the meantime I've got to put some more thought into this fall's trip.