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My suggestion with your preference of two nights anchoring and one night docking:
Night #1: Anchor: Shaw Bay or Wye River (via Kent Narrows)
to Eastern Bay, around Bloody Point, North to...
Night #2: Marina Annapolis--Port Annapolis Marina--Price is less than $3/foot for transients, has a pool, Water Taxi into Annapolis;
North to.....
Night #3:Anchor either behind Dobbins Island OR
Northeast to Corsica River (via Chester River)
then South back to Rock Hall.
Enjoy
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