Since you're in the US (technically) I'd offer that you do something in unusual. Hit Cancun Mexico. It's now a wing destination from Nov til March at least. Tropical, fun culture (if you avoid the main tourist traps) and a stoked group of local foilers. Check out
@foilero coulero and @maxico25 in Instagram. They will give you an idea of conditions.
South FL rocks (as does Texas and the rest of the Gulf, though the scenes in other states aren't as developed. ) Winging will open the world for "surf" travel in the next couple of years.