There is the Winter Guide to Kiting in Florida, it is a bit early so it hasn't gone back up to the top yet,
http://fksa.org/showthread.php?t=903
BigR has covered it pretty well. No wind may describe things for periods of summer but is far from accurate for the winter months. The winds do come and go with fronts with calm periods. I have yet to go there in winter but understand the trades can be up and down in the Hawaiian Islands in winter. Absent hurricanes to mess up the trades summer is a more consistent time as a rule. As far areas with interesting things to do off the water for a whole winter, it would seem South Florida and Hawaii would have some good prospects in that area. Southwest Texas on the Gulf can have some good winds but even those break up at times I understand. Shore side pursuits for several months might be more limited there too depending on your interests. I would take a hard look at either South Florida, maybe even move around a bit from Jupiter down to the Keys and up to Tampa depending on conditions or head to Hawaii. You could look at the wind archives on ikitesurf for more historical wind info. Wind isn't nearly at the same intensity among all the Hawaiian Islands either, more choices. Have a good winter wherever you land!