Leaving the mouth of the Chesapeake you have...
Chincoteague....not great but follow someone in or ask to be lead in in less than great conditions. Used to have a town dock.
Ocean City, Md......pretty good inlet with several marinas.
Indian River Inlet.....not a real bad inlet but strong current. Large bay inside with a couple marinas.
And that is pretty much it with a long distance between any port in the Chesapeake till Chincoteague.
Not many optionas to pull in.
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