Just a thought. On either the trip south or back north consider going outside from the mouth of the Chesapeake up the coast back to Cape May. The point being, that would be one of the minor circumnavigation trips in the country to check off a box. Circumnavigate the Delmarva Peninsula.
Heading south from either Cape May or Lewes, the next stop is Ocean City MD. From there to Chincoteague VA. Between there and the Chesapeake is likely an anchoring stop unless you are into an overnight run.
Just a thought.
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