There should be a few places in Annapolis. You might inquire with the sailing schools. If you want to go sporty, J-World/J-Port in Annapolis might let you rent out a J-80, which would be a good choice but $$$.
A Flying Scot would be good if it wasn't too choppy/windy. Otherwise, you'd want to limit the trip to well protected waters if the wind is piping up, unless you like getting wet/beaten up.
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT