The upper bay is little too far from my home port on the Patuxent River for anything less than a week's cruise.  Other than a trip to the Baltimore Inner Harbor back in the 70's, most of my cruising north of the Bay Bridge has been in transiting between the Chesapeake and Delaware Bays by way of the C&D Canal.

I have stopped in a number of creeks and bays on these trips, but they were picked for their quick access to the bay.  These destinations included Silery Bay on the Magothy; Fairlee Creek, Worton Creek, and Bohemia Creek.