re: Key West at end of May

Definitely do a full day fishing charter if you're in to that. You can stay closer over a reef or structure and fish for yellowtail snapper (so good). Or go further out looking for Mahi Mahi. They'll filet them for you at the dock obviously. Then take them to Dante's at the north end of Duvall St. and they'll cook it for you. I recommend it blackened and fried, the grilled doesn't have much flavor.

The strip of bars on Duvall is a great time obviously.