While I can't help with the Naples bit... I'm gonna guess you learned at Community Boating, given the Cape Cod Mercury and Charles River/Boston references in your post.
I'm going to be in Naples, Florida for work later this month. I want to rent a boat for a few hours per day to become more proficient and practice what I've learned so far about sailing.
I just learned how to sail last summer on the Charles River in Boston. I'm comfortable in a small centerboard Cape Cod Mercury (15' sloop). I also have sailed a 13' Hobie Wave catamaran.
Any suggestions would be greatly appreciated. Thanks!
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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.