Villa Notman in Kongens Quarter, Charlotte Amalie, St. Thomas Island, U.S. Virgin Islands, West Indies
It's that time of year again. Temperatures plunge, snow begins to fall, and your thoughts invariably turn toward warmer climes. Wouldn't it be wonderful to leave your cares behind and take a leisurely vacation to a tropical island or a Caribbean paradise?

On second thought, why stop at a vacation? Why not start a whole new life where it's warm year-round, where you can sit on the beach at lunch and fall asleep to the sound of the rolling waves? Why not move to the tropics?

I've done it. In 2012, I pulled up stakes from northern Virginia and moved to the U.S. Virgin Islands. Along the way, I learned a lot about how to make a move to paradise work, and I also learned how to cope with the subtle but meaningful differences between life on the mainland and life on an island.

Here's how to make a move to paradise as perfect as possible.

Step 1: Know What You Want

A long-term international is complex on a host of levels. Simply gaining legal residency in a foreign tropical country can be a paperwork nightmare. So, before you even book a trip to your potential new home, make sure you answer a few basic questions:
  • What can you afford to spend each month on rent?
  • How close to "modern" do you need your new home to be?
  • Will you want to get around in a car, a golf cart, a Jeep, or a boat?
  • Are you willing to speak or learn a language other than English?
  • How do you plan to earn a living (if you're not retired)?
  • How much of compatible social scene do you need for an enjoyable lifestyle?
  • Are you intending to relocate for years, or only a few months?
Once you've figured out what you're looking for, you can start narrowing your search down to specific locales. After answering these questions for myself, I chose the Virgin Islands because, as a U.S. territory, it offers many of the laws, amenities, and social structures I'd gotten used to on the mainland while also retaining much of the laid-back tropical charm you find elsewhere in the Caribbean.

Unless you're retired, earning a living will be of paramount concern. The economies of most tropical locations are tilted heavily toward tourism -- career opportunities for specialized professionals can be few and far between. A tropical move will be much easier for those who can telecommute (as I do), but even then, you'd best make sure that you can get a reliable Internet connection or emails will pile up, conference calls will be missed, and your job performance will suffer.

Once you've identified your top choice for a new tropical home, it's time to pay it a visit.

Step 2: Book a Trip

You know where you want to live, and you've even identified a few possible places to rent thanks to helpful online listings (though there may not be as many as you'd expect from which to choose). Now you've got to see for yourself if the tropical lifestyle is really for you.

Get yourself a plane ticket and a place to stay, but don't reserve a posh hotel -- hunt around on Airbnb or HomeAway (AWAY) and its sister site VRBO for a genuine tropical residence to rent for your stay, preferably one that's reasonably close to the area you'd like to live in long-term, and reasonably similar to the sort of place you'd intend to rent long-term as well.

Stay as long as you can -- if you spend all your time looking for places to live, you can miss out on the local quirks that will color your experience when you move for good.

Step 3: Find Your New Home

I haven't mentioned buying a property, and there's a good reason for that. Property ownership laws and mortgage requirements can vary widely from place to place, and you're just getting started on your tropical adventure. Plus, it's unwise to buy a piece of the tropical lifestyle before you know for sure that you want to stick around.

Renting first will give you the opportunity to fully familiarize yourself with the laws and financial requirements of local property ownership should you decide to take the plunge later.

Most tropical locations are bound to have their fair share of available rentals, and a combination of remoteness and low local median incomes can keep many of the best options on the market for months. As a bonus, renting locally before you buy a home will give you an inside track to better deals that may never show up online.

Step 4: Make a Shopping List

While you look for housing, keep in mind that you simply won't be able to bring much more than the clothes off your back when you do move. Many tropical rentals are furnished, but you're still likely to have to fill in a few holes. I needed a desk to work on and new cookware, but every situation is unique.

Don't expect to easily fulfill your shopping list via Amazon (AMZN). Few major American retailers reliably ship to the Virgin Islands, and you can't expect to get e-tailers to deliver to Belize or Bali at all unless you first go to the trouble of setting up a complex shipping scheme with specialized intermediaries.

Get to know local retail outlets, their offerings, and their prices as you hunt for a place to stay. The cost of goods can vary widely from place to place, and many tropical locations can be lacking in retail diversity. This part of your search will both help you figure out how much your monthly non-rent expenses might be and help you figure out what you absolutely need that won't be available locally.

Step 5: Make the Move

You've found your place, you've filled in the blanks, and you've (hopefully) figured out how you'll be able to pay for it all. Once you're back from your exploratory trip, you should have some time to tie up loose ends before the big move.

Say goodbye to the things you won't need and the people you'll be leaving behind, and pack up only what you really need -- you're moving to paradise now!

Motley Fool contributor Alex Planes holds no financial position in any company mentioned here. Add him on Google Plus or follow him on Twitter @TMFBiggles. The Motley Fool recommends and HomeAway. The Motley Fool owns shares of

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Thanks for the moving tips! I want to uproot from Virginai to Key West and was thinking what I need to get done to make it happen. Good luck and enjoy your life on the Island. I lived in Honolulu for a number of years and Island life was great. Vaden

January 31 2014 at 5:36 AM Report abuse rate up rate down Reply
1 reply to Vaden's comment

Moving to the Keys will be great if you're gay.

January 31 2014 at 10:33 PM Report abuse rate up rate down Reply

irq, Baaaaaaaaaaaaaaaaarack. Excuse me.

January 30 2014 at 8:27 PM Report abuse rate up rate down Reply

If you move to south Florida, learn to speak Spanish, Senor.

January 30 2014 at 8:17 PM Report abuse rate up rate down Reply

Florida used to be paradise. It was 22 degrees here. Miami is wrapped up with Cubans.

January 30 2014 at 5:17 PM Report abuse rate up rate down Reply

Also on here is a story about a man sueing NASA for not investigating what looks like an alien on Mars. I wouldn't.
I was more driven than this guy to find answers. I heard about a sighting twelve miles north of pad 39B. I went there and looked around. I didn't find anything, but what happened later I was not prepared for. All of the Star Trek and Sci-Fi I had ever seen didn't prepare me for what happened.

January 30 2014 at 2:46 PM Report abuse -2 rate up rate down Reply

somebody needs to check more on the best places to retire list! st George, Utah is know as a downwinder from the atomic bomb tests ahd has more cancer than any city in america, as far as cour de laine, idaho goes, it is one of the coldest spots in the US, if you want to freeze be sure to go there to live.

January 30 2014 at 2:11 PM Report abuse rate up rate down Reply

Happy for you Alex! Best wishes and thank you for the advise...

January 30 2014 at 12:31 PM Report abuse rate up rate down Reply

that's it ..... ???? what a trite article

January 30 2014 at 11:25 AM Report abuse +1 rate up rate down Reply

Liberals need to find a place that has good Government Handouts available.

January 30 2014 at 10:09 AM Report abuse rate up rate down Reply

That is the most useless poorly written article Ive read in a while. I dream about moving out of NYC to tropical islands everyday in winter, but tell me something we all dont know.

January 30 2014 at 9:30 AM Report abuse +1 rate up rate down Reply