Having sailed the Hampton Roads
area, if you are buying
a day sailer, I'd look at a swing keel
or center board boat
. The sand bars do shift in the Bay and you WILL run aground. While you can get out and push, lifting the keel
and floating off is easier and passing boats might not even know you scrubbed the bottom of your boat.
The boat, Chessie Flyer comes to mind.