Re: Overnight Sails on the Bay
I'll second some of the choices. From Herring, Oxford, St Mikes, Cambridge (marina stop), Annapolis are all very easy sails. Slightly longer but worth it are Solomon's, Rock Hall and Queenstown. Not towns, but accessible by car to meet up with your friends are Rhode River (car to the small ramp next to the Smithsonian), Whitehall (Cantlers), Magothy (Deep Creek).
We also sail out Herring (HHN). Would love to meet up sometime and compare notes.