relax your from FLA you'll be fine. treat it almost like home flip flops will work if working on the boat then any kind of tennis shoes, boat shoes will be fine and yes when leaving fla only because it is cold in the airport i (girl) wear long pants that can be rolled up and a tank underneath a tshirt and usually the moment you land the tshirt comes off (with the tank underneath) take a breath your there and everything will fall into place have a great time