Smith Island
Click on chart to view at full resolutionSmith Island provides the visiting yachtsman with an insight into the Chesapeake Bay waterman lifestyle.  Virtually everyone on the island earns his living from the Bay.
The normal entrance to the harbor at Ewell is via the Big Thorofare from the Bay side of the island.  There are also entrances from the Tangier side, but I'm not sure they are suitable for deep draft vessels.
Smith Island is one of those destinations I visited in the first two years I owned a cruising sailboat and haven't returned in the ensuing 30+ years.  I can't say why that is so, I guess it's just the result of so many other options and the limitations of weekend sailing.
Unfortunately on my only visit I failed to take a single picture.