Herring Bay

Herring Bay sits on the western shore of the Chesapeake Bay, about 20 miles south of Annapolis in Anne Arundel County, Maryland — a solid anchorage if you're working your way up or down this stretch of the Bay. It's a well-known gathering spot for DC-area sailors, and the surrounding Coastal Plain gives it a low, open feel with wide water views. Drop the hook here and you've got easy access to one of the mid-Bay's more social corners.