It depends on how much time you have... many days we go out, just to go out... and be on the water. Sailing is more about being out on the boat than having a specific destination. If you're really interested in getting to a destination, you shouldn't be looking for a sailboat.
There was a recent thread on good destinations for the Chesapeake.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.