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

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Villa Notman in Kongens Quarter, Charlotte Amalie, St. Thomas Island, U.S. Virgin Islands, West Indies
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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!

13 PHOTOS
25 Best Places to Retire
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Ready to Escape the Cold and Move to Paradise? Here's Your Checklist

Whether you dream of retiring to a big city, small town, resort area or college town, these great places offer reasonably priced homes, low crime and tax rates, quality health care, and more.

Photo: John Tuggle, Flickr.com

By CNNMoney

Best if you're looking for:Resort area
Median home price:$156,000
Top state income tax:None
Legend has it that explorer Juan Ponce de León set foot in St. Augustine nearly 500 years ago and discovered the elusive fountain of youth. Alas, a move to the city today probably won't turn back the clock (in fact, de León may not have ever been in St. Augustine).
But St. Augustine's fantastic weather, beautiful beaches, and world-class golf will certainly do a body good. Although this small city 38 miles southeast of Jacksonville is a popular tourist destination, it has an active year-round community and lots of housing options. Its Flagler Hospital ranks among the top in the nation for clinical excellence and patient safety.

By CNNMoney

Best if you're looking for:Resort area
Median home price:$259,000
Top state income tax:7.4%
Visit Coeur d'Alene and you'll immediately understand why this northern Idaho outpost is known as "Lake City." That lake, also named Coeur d'Alene, stretches 25 miles and has 109 miles of shoreline.
During the summer, it's a flurry of sailboats and cruise boats, paddlers and swimmers (even the 14th hole of the Coeur d'Alene Resort Golf Course sits amid the lake on a floating green).
Winters are chilly, but when locals aren't spending time in the three nearby ski resorts, they can be found warming up in the city's numerous restaurants and breweries or making the quick 30-mile trip to Spokane for more urban pleasures.

By CNNMoney

Best if you're looking for:Resort area
Median home price:$195,000
Top state income tax:4.35% (4.25% in 2013)
Retiring to the water doesn't have to mean giving up four seasons or downsizing to a tiny condo. In Traverse City, residents enjoy miles of sandy beaches and all the spoils of Lake Michigan and nearby inland lakes-where waterfront homes can be found for less than $200,000.
Moreover, despite Traverse City's location on the northwestern side of the state, it has fairly urban-like amenities, such as the 391-bed Munson Medical Center, which consistently ranks among the 100 top hospitals in the country. And the nearby Interlochen Center for the Arts brings in hundreds of concerts, art exhibits, and theatrical and dance productions each year.

By CNNMoney

Best if you're looking for:Resort area
Median home price:$264,500
Top state income tax:5%
Two hours northeast of Las Vegas, St. George is a favorite spot for both snowbirds and full-time retirees. Golfers can play on a dozen different courses in more than 300 days of sun. Hikers can traverse any number of trails in or near town, or take an hour's drive to Zion National Park.
While nature has carved monolithic masterpieces in the surrounding countryside, area artists are just as prolific; St. George's Tony Award--winning Utah Shakespeare Festival runs from June through October.
Meanwhile, the Tuacahn Amphitheatre in nearby Ivins brings Broadway shows and other big acts to its $25 million venue.

By CNNMoney

Best if you're looking for:Big city
Median home price:$129,000
Top state income tax:7.75%
This central North Carolina city has a longstanding tradition supporting the arts. Its symphony, founded in 1947, is the oldest in the state; its arts council was the first in the nation; and the University of North Carolina School of the Arts is among the most prestigious in the country.
The city also plays host to an internationally recognized film festival.
More draws for retirees include affordable housing (downtown townhomes can be had for $200,000) and tremendous health care, thanks in part to university teaching hospital Wake Forest Baptist Medical Center.

By CNNMoney

Best if you're looking for:Big city
Median home price:$215,000
Top state income tax:None
Austin's relatively strong job market has made it a top destination for young folks in recent years. But retirees also feel at home in this vibrant city; of the more than 20 city-run recreational centers, three cater specifically to seniors.
There's something for everyone here whether you're looking to consult with a startup, hear live music on Sixth Street virtually every night of the week, or volunteer at South by Southwest's lollapalooza of music, independent film, and technology.
Meanwhile, the city boasts terrific health care and a performing arts scene that runs the gamut from ballet to the Shanghai Quartet.

By CNNMoney

Best if you're looking for:Big city
Median home price:$116,000
Top state income tax:6%
The first Saturday in May, all eyes are on Louisville, home to the Kentucky Derby. Yet there's also plenty else to do and see year-round.
Residents can hear live bluegrass music, museum hop on West Main Street downtown, attend a concert or festival in the 85-acre Waterfront Park, and see local and Broadway shows in the Kentucky Center for the Performing Arts.
Keep in shape by biking or strolling the Louisville Loop, a pedestrian path that will eventually span more than 100 miles, connecting many of Louisville's parks, neighborhoods, and attractions.

By CNNMoney

Best if you're looking for:Big city
Median home price:$272,000
Top state income tax:9.9%; no sales tax
Famous for its food and bike cultures, Portland is a thriving but manageable city that gives retirees easy access to just about anything.
To see a revolving door of art exhibits, performing arts, and festivals, look no further than downtown and the nearby Pearl District.
No need to leave the city for outdoor adventures; Portland has one of the largest urban forests in the country (wine country and beaches are just a short drive away). It's also home to several award-winning hospitals, including the Oregon Health & Sciences University, whose research center attracts experts and patients from around the country.

By CNNMoney

Best if you're looking for:Big city
Median home price:$174,000
Top state income tax:4.9%
There is much to be said for a place where you can ski in the morning and golf in the afternoon; drink Italian-style espresso at breakfast and eat homemade sopapillas for lunch; see ancient petroglyphs one day and gallery hop the next.
With the Rio Grande river near downtown and the Sandia Mountains to the east, Albuquerque is as diverse in its landscape as it is in culture. Downtown revitalization projects have added considerably to the appeal.
One caveat: Crime is on the high side, though locals say it's easy to avoid the problem areas.

By CNNMoney

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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 Amazon.com and HomeAway. The Motley Fool owns shares of Amazon.com.
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