Ready to Escape the Cold and Move to Paradise? Here's Your Checklist

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

Originally published