Bahamas ... Florida Keys ... ?
 

There is a vast amount of info on both the Bahamas and Florida Keys on here. Word searches should lead to a lot of useful stuff. There's an article on Nassau and Spanish Wells HERE and one on Key West HERE. A personal favorite in the Family Islands are some of the islands in the Abacos. Some photos and info along those lines appear HERE and HERE. You can check historic winds at various stations in the Keys on ikitesurf.

I spend a lot of time in the Keys and as much in the Bahamas as I can manage, heading over there soon. There are different in many respects and both have things to offer to the traveling kiter. As far as wind, due to gradient effects across from the frequent Bermuda High, deepwater of the Straits and influence of the Gulf of Mexico, the Keys see more wind more of the year than most other parts of mainland Florida that come to mind. I've yet to land in the Exumas, may fix that soon. Don't have a great feel for wind conditions there. There is some info in that regard HERE.