Idea for you.
In Annapolis there is the J-Port Sailing Club. Basically you pay a fee and get use of J-80's (26') I think a J-32 cruiser, and a J-105 (34'). They will make all new members take a weekend sailing course just to be sure you have the minimum skills.
My experience over 4 years was excellent. No trouble at all getting a boat when I wanted it, well kept, far cheaper than ownership, all the hassles of slips, insurance, registration and repairs taken care of for you.
They have an excellent web site.