We live in the Whitemarsh/ Parkville area about 15 minutes from Aberdeen and keep our boat in Rock Creek on the Patapsco about 35 minutes away.
This a central location which you can take a days sail and get to anywhere in the northern Chesapeake ( Middle River, Sassafras River, Bohemia River, Still Pond, Worton Creek), anywhere on the Chester River (Langford Creek, Cackaway, Greys Inn Creek, Corsica Rivers) St Micheals, anywhere south (Annapolis, Severn River Magothy River, Whitehall Bay, South, West and Rhode Rivers. This means these are great weekend anchorages.
There are also days you cannot sail the Bay as it is to windy..rough, but you can cruise the Patapsco up to Inner harbor. Rock Creek means you can put your sails up 5 minutes from the dock and are never really worried about "skinny water". We are virtually on the corner of the Bay and the River so there is no extra time getting out to the Bay.
My next choice would be Middle River