Guess it depends on what you are looking for - here are a few spots we enjoyed:
South - try the West River. Galesville is a neat little town.
North - go thru the Bay Bridge and head
for the Magothy if the wind
is NOT on the nose (it is always on the nose for us).
Alternatively, go thru the Bay Bridge and head
NE. Go to either Rock Hall or go up the beautiful Chester River and select an anchorage like Grays Inn Creek or the Langford (sp?), or the Corsica
- all quiet, scenic just super relaxing spots.