The 5 Best Places in the World to Retire

By David Sterman
April 05, 2011

With another tough winter looming in the future, many aging baby boomers are dreaming of the day that they can pull up roots and spend their retirement years in a cheerier place. For many, that means Florida or Arizona. But for a growing number of retirees, the net is being cast much wider.

These retirees are willing to travel far distances to set up camp in a new country. Luckily, Uncle Sam is still pretty good about sending Social Security checks wherever you go. So moving abroad doesn't have to be a financially risky move.

Of course, where you end up depends on what you're looking for. Some retirees really need to stretch their dollars and will give up many conveniences. These include:

  • Proximity to a nearby international airport so they can visit loved ones quickly and easily

  • Living among locals rather than in a gated community

  • Less-than-ideal weather, especially brutally hot summers if you're not near the sea.

Whenever I travel, I play the game "Could I live here?" Who knows, maybe one day I'll get lucky. Of all the places I've visited, these five hold great appeal. Each one is unique and may be just what you're looking for.

The Caribbean
Pros: From hiking waterfalls to diving amongst shipwrecks, plenty to appeal to the active retiree.
Cons: Most island countries are dependent on imports for the basics, meaning prices can be high.
Place You Have to See: Pico Duarte, the Dominican Republic, for views from the highest mountain in the Caribbean.

I used to live in The Dominican Republic, and it has always been a magnet for me to keep coming back. The cost of living is quite low, the fairly large island nation offers culture, beaches and mountains, and you'll likely never be bored. On the flip side, the D.R. perennially battles power problems, so unless you have your own generator, be prepared for nightly blackouts. And while the country once had very low crime rates (at least against foreigners), it has become less safe in recent years, though you shouldn't have much trouble if you use common sense. The rest of the Caribbean can get pricey, although if Cuba opens up in coming years, that country could prove to be the low-cost destination in the region.

Central America
Pros: Many major destinations are high in the mountains, creating perfect weather conditions.
Cons: A decent amount of Spanish is essential to go off the beaten path.
Place You Have to See: Eating breakfast amid toucans and howler monkeys in Guanacaste, Costa Rica.

Costa Rica remains as one of the most beautiful countries in the Western Hemisphere, and it's also quite safe. Yet it's awfully hard to find a bargain, so be prepared to spend $200,000 -- or more -- to find a place to your liking. Panama is also quite beautiful, but caters to an even higher-end set of retirees, so it may not be the place for you if you're looking to stretch your dollars.  If you've got a pioneer spirit, your dollars will go very far in Nicaragua. The country has its shares of social and political strife, though Americans are largely unaffected. The Nicaraguan town of Granada may rank as one of the prettiest "colonial" cities that an expat will ever find.

South America
Pros: Friendly people, low cost-of-living (in most countries), summer when we're in winter.
Cons: Poverty remains intractable, subject to extreme weather, earthquakes.
Place You Have to See: The home of poet Pablo Neruda in Valparaiso, Chile.

Argentina continues to be a magnet for U.S. retirees, but the country is no longer the stunning bargain that it was a decade ago when its currency was sharply devalued. Buenos Aires, the country's grand capital, is ideal for retirees that prefer a sophisticated urban lifestyle. Some retirees are increasingly exploring neighboring Uruguay, which shares Argentina's Euro-style ambience, even if that ambience is a bit faded. My personal choice in the region is Colombia, which is just now throwing off the shackles of a violently destructive era. The newfound calm has allowed visitors to discover a very cosmopolitan place, highlighted by a thriving arts scene, world-class restaurants, breathtaking scenery just minutes from the major cities and a reasonable (although not cheap) cost-of-living.

Asia
Pros: Gorgeous beaches, inventive cuisine, historically-rooted cultures.
Cons: Cities can be quite overcrowded. Ai pollution in some cities can be choking.
Place You Have to See: Nikko Botanical Gardens in Japan on a fog-shrouded spring morning.

This region has two clear strikes against it: Relatively few English speakers, and a vast distance to cover if you have to get home to a family emergency. But if that's not a problem for you, then Asia holds some of the most beautiful beach and mountain towns you're likely to ever find. And the values are incredible. The cost of living is so much lower that one can live quite comfortably simply on a Social Security check. Although many flock to exotic places such as Thailand or Hong Kong, my personal favorite is Vietnam. Forget what you might think about lingering tensions after the U.S.-Vietnam war. You could not find a kinder group of people that have thankfully not been swept up in the homogenizing waves of global culture. To be in Vietnam means being in another era, where life's daily rhythms are focused on preparations for the next meal, or a nap under a shade tree. Halong Bay, in the North of Vietnam, surely qualifies as "one of the places to go before you die."

Europe
Pros: A museum around every corner. Lively social discussions with locals in cafes and pubs.
Cons: Quite pricey in the most popular regions. No shortage of opinions on America's flaws.
Place You Have to See: Singers wailing out "Fado" songs in the hills of Lisbon, Portugal.

Forgetting the lure of Paris for a moment, retirees may be surprised at the values to be had now in Southern Europe. Places such as Greece, Spain and Portugal are going through wrenching changes, which means that many formerly pricey communities in choice locations can now be had for a bargain price as the real estate boom of the last decades left these communities with vast tracts of under-utilized housing. These countries will eventually rebound, and that slack real estate will eventually be restored, but you can find real bargains there if you're willing to jump in while the economic upheavals persist.

Before making any major moves, you need to explore these areas in much more depth. Take out a three-month lease in a furnished apartment and go live among the locals. By the end of your stay, you'll have a clear sense of whether you've found a new home.

If I were to focus on one aspect, these would be my personal top five retirement choices.

Perfect weather: San Jose, Costa Rica.
Perfectly prepared meal every night: Hanoi, Vietnam
If money were no object: Sydney, Australia
Living in an atmospheric 19th century novel: Cartagena, Colombia
The remoteness of Gilligan's Island: Las Terrenas, Dominican Republic

[InvestingAnswers Feature: 5 Tips for Cheap International Travel]

Images Attributed to the Following:
Dominican Republic Coastline -- Thierry
Grenada, Nicaragua -- David Garcia
Cartagena, Colombia -- Pedro Szekely
Halong Bay, Vietnam -- Aftab Uzzaman
Santorini (Greek Isles) -- Lynnder