I am not a huge fan of Florida (I like going to places with more interesting history, and preferably less heat), but with our deep chill so early this year, I have been thinking about it a little.
I am not really a Hobe Sound or Jupiter type, and definitely not a Palm Beach sort. And Vero Beach never sounds very interesting to me. Your editor is averse to "relaxation," and also does not want to waste time by playing that game where you hit the little ball with the little stick.
Islamorada, for the fishing etc. I am also attracted to Gasparilla and Useppa. When we did a week in Captiva a few years ago, we'd rent a boat and tool around the waters between Captiva and Port Charlotte. We had to boat to have lunch in that wacky place on Cabbage Key, and we anchored right off Useppa for a swim and for some exploring.
Cabbage Key has no roads, and there is an insane drunk directing the boat traffic. Gasparilla and Useppa have no cars. They are both clubs. I am told that Gasparilla is for stuffy blue-bloods (it's rustic and simple), and Useppa more for the nouveaus - more luxurious. Tiny Useppa looks to have been having a building boom since we were down there.
A brief history of Gasparilla and Useppa, including how they got their names.
The Gasparilla site here.
Here's a Useppa site. Here are some of their cottages.
If any of our readers like to go to Florida, where and why?