As a 12 year resident of Key West, I would tell you that the weather changes in the keys over the past 5 years have made almost everyplace windy all the time until summer. It is also not warm in or out of the water.
The best place for you in a Kayak is Key West. Boyd's campground on Stock Island is an A-1 (not cheap) place. Because of the way the island is laid out you can always find a sheltered spot to paddle or fish.
If you go now, wear a wetsuit. There are good eating fish like Mangrove snapper to be caught inshore right in the marinas, harbor and the cuts. May brings the Tarpon and the sharks that eat them. Once summer is in full swing you will find platter of pizz days that you can fish the reefs and wrecks for Yellowtail snapper
(the best eater).
Best budget resturant is Bobalu's Southern Café, on big Coppit Key, down home Southern and the best Boston Pizza in FL. The best period is LaTeDa downtown and don't miss Randy Roberts or Christopher Peterson at the cabaret there. (Unless you have a problem with talented gay men doing female icons) They are not fake lip synchers but very talented actors who appear in Vegas and other major venues.
Randy does Cher better than Cher !
http://www.randyroberts.net/photo.htmlStay away from the Cruise ship end of Duval street as it's all too loud bars and ripoff tourist traps, except:
The sunset show on Mallory square is also a must do as is the Customs House museum and the Conch train ride.
Lots to do and contrary to some of the paranoid homophobes on this site you will not in any danger of being molested.
Enjoy !
