Middle Tn is where I live and also have a beach house in the pan handle of Fl it still can go down past freezing in the winter in Fl and the water is swimmable only April-Oct. So year round swimmable was my goal with equal travel time from Tn.
The Caribbean seemed the logical place. My first consideration was that of language (I speak English). So Jamaica was the first place on the list to check out, due to the sheer beauty. Mountains rain forrests and rivers make up this paridise. The locals were always working an angle, it became tiresome.
The Caymans were ruled out due to topography. When the last Major storm hit there, all land in the Caymans was submerged by a minimum of 4 ft of water.(very flat) So if you were there buildings stuck out of the water but the closest unsubmerged land was Cuba or Jamiaca each >100 miles away.
In Dec. the Us Virgin Islands became my next adventure. They speak english and the US$ is the currency. My intentions were serious about a move there. I brought along my banker who grew up and is very well connected in the USVI. His ancestors arrived there in the early 1800s. I was presented the island at its best. To make a long story short. After spending time there, my realization was that Island life takes some getting use to.
If you have an intrest in USVI. vitrader.com has a relocation package. Which includes newspapers, maps, the local homes for sale mag, and The Settlers Hand Book. If memory serves me corectly the paclage was about $30.(worth every penny) I also ordered a USVI telephone book, This has to be done through the tele co. The area code for the USVI is 340 so calling it is a simple long distance call and long distance is included on most cell phone plans. With a Virgin Moble phone (no contracts) you can activate it as USVI phone then you have a local # when you arrive. Just give 00802 as the zip during activation.
My main sugestion is to rent for several months before you buy. Any where you might like to live.