Shovel Snow or Sift Sand.

You can take your choice, but based on the weather predictions for much of the USA, many of us are, or soon will be shoveling snow or at least dealing with some very cold weather.  We all make choices in life.  There are ways to enjoy tropical weather and not have to cash in the retirement fund to do it.  I might suggest, for those interested, begin with a reading exercise at International Living on the Web.

After plenty of research and your head is spinning, if you are like me, you will want to immerse yourself in the lifestyle of several warm climate locations over a period of time.  After being there and doing that you should easily be able to decide between being an expat, a winter visitor, or trying another spot.  

Beware, there is no perfect place for any of the above.  There are places that are tolerable, wonderful, and "not my cup of tea".  Financial considerations, length of legal stay at any one time, and the stability of the country also play an important part in most people's decisions.

It feels like International Living loves Ecuador, for instance.  You can read some not so good things about the country, but thousands of well traveled Americans can't be wrong?  Personally, I have to live it to believe it, I need to interview a multitude of people in person who think a particular country is a great location to settle in (for however long), and I need to see first hand that affordability of living is an accurate description.

In a nutshell, what I am advising is that finding a regular Caribbean/warm weather escape will require several in-person visits, and asking a lot of people a lot of questions.  Whether it be for a week, a month, or the rest of your years, there will always be some trade off.  I am more than willing to exchange my snow shovel and heat bill for periodic power outages, a requirement to leave the country every 3 months for a day, or not having access to my favorite US beer.  

"I blew out my flip-flop  Stepped on a pop-top......"      Travel Safe, Travel Often.