Florida is definitely a go. Pinellas county has some of the best kiteboarding in Florida... (aside from the keys). We can ride flat water in any direction... and (small) waves anytime we get some West in it... for big waves in an East you can make a drive to the east coast but it's 3 hours away... but worth it if you want to pick up some gear cheap from extreme kites.

You can also do a down winder for about 10 miles on the gulf and take a trolley back to where you started... gear and all for $1.50. Just wear booties and a rash guard (or wetsuit) to get on the trolley.