Naples is a tough call, you need to follow the cold fronts but I've found it to be on the light side most of the time so bring big gear. I actually ship my 16m & Door down and let them live in Naples for the winter and I have yet to ride anything else but I seem to be 100% not in sink with cold fronts
I'm sure Latino will chime in here and check in with Jeff at the "Old Naples Surfshop" he's a kiter and also rents SUP's.