I would third the suggestion for chartering out of Rock Hall -- it's far enough down the Bay that you can get into good sailing waters fairly quickly, and it's a nice destination unto itself. Also it's probably not such a long drive from where you live.
If you don't mind doing some extra driving, there are plenty of charter outfits in Annapolis. One that you might want to look into is J-Port, which has a club with an annual membership that guarantees you a certain number of weekends a year on nice quality J-Boats. If I'm not mistaken, they have performance daysailers (J-80s), racers (J-105s), and performance cruisers (J-32s) available for members to use. That J-32 is an almost ideal boat for poking around the Bay!
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT