Definitely need air conditioning on the boat, to hang out dockside or to cool off after doing any on deck work.
Ha! I grew up living aboard in Clearwater, no AC, no heater. We had hatches and fans and our bunks were upholstered in vinyl. There were miserable times, but really, it wasn't that hard. Of course, I was born to it. Up here in the great Northeast, native complain about the cold but don't wear extra socks or long underwear. I do and I'm fine. What's funny is how my wife complains more about my extra layers of clothes than she does about the cold. She treats my dressing for the weather as a complaint about it.
I like sailing Florida. I like Summer sailing in Florida. From my exprience living aboard, it was a great way to cool down. Our there with the breeze, it was better than at the dock. Of course, of you have a house with AC, it's cooler to not go to the boat at all.
We sailed to Key West and Dry Tortugas every year, up to Cedar Key and Carribell and occasionally to Yankeytown, Apalachicola and Panama City. I highly recommend the seafood (especially shrimp and oysters) in Apalach.
The Florida State government is interested in making boating easy for everyone. Individual town governments, not necessarily. The West coast is definitely better than the East coast.
I would be right there with all the other native Floridians, telling you how horrible it is there and not to come, but I've discovered Puerto Rico. Since I like to wallow in misery, this is where I plan to retire to and sail out of. Florida has become too nice a place for me.
-Will (Dragonfly)