5 Easiest Places to Retire Overseas in 2020: Best Havens for Fitting in Fast—Internationalliving.com

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A new report from International Living pinpoints the top 5 retirement havens around the world where it’s easiest to “fit in.” IL’s Annual Global Retirement Index 2020 ranks and rates 24 countries across 10 categories, including “Fitting in and Entertainment,” which considers the character of the expat community, whether English is widely spoken, how easy it is for a single or LGBT person to acclimate, how welcoming locals are, and more.

Great Places to Retire Where it’s Easy to Fit In

Great Places to Retire Where it’s Easy to Fit In

"This ‘Fitting in and Entertainment’ category of our Annual Global Retirement Index 2020 points to the locations where it’s easiest to get comfortable quickly, make friends, and connect in the community."

“It’s important to feel comfortable in your new home abroad. Of course, part of the adventure—and the attraction—of retiring to a new country is discovering new customs, new foods, new people,” says Jennifer Stevens, Executive Editor of International Living. “But at the same time, settling in can be a challenge. And in some places, it’s simply easier to do than in others.

“This ‘Fitting in and Entertainment’ category of our Annual Global Retirement Index 2020 points to the locations where it’s easiest to get comfortable quickly, make friends, and connect in the community.

“There’s no one-size-fits-all destination, of course, but expats say that when you can buy some familiar items at the grocery store, plug in to an established group of expats who already know the ropes, maybe see a movie in English, easily make friends with locals, find people who speak English...all those sorts of things help to make life in a new place more comfortable, faster.”

The countries that rank the highest in the Fitting-in and Entertainment category of International Living’s Annual Global Retirement Index 2020 are….


Mexico claims top rankings in the Fitting in and Entertainment category of this year’s Annual Global Retirement Index, scoring 96 points.

Mexico is, by large numbers, one of the most popular retirement destinations on the planet, for U.S. expats. Some move here full-time and some live in Mexico part-time—spending winter months in vacation homes where the weather is always warm and the cervezas are always cold. U.S. citizens can stay for six months at a time in Mexico on a tourist visa, which makes it logistically easy to snow-bird there.

“With more than 1.5 million American and Canadians calling Mexico their full-time or part-time home in dozens of destinations around the country, you’ll have no trouble making friends and finding things to do just about anywhere you choose to settle down in Mexico,” says Jason Holland, IL Roving Latin America Editor.

“The expat community is welcoming and eager to help newcomers… and your Mexican neighbors will be warm and friendly. And there is always something going on, from traditional celebrations and festivals to live music, clubs for every activity, sunset happy hours, holiday dinners, social gatherings, and much, much more.”

Portugal and Costa Rica are tied for second place with 91 points.


Long an under-the-radar destination, today Portugal’s low costs, historic towns, warm weather, and varied landscapes are attracting North Americans in increasing numbers.

Rich in culture, Portugal offers much adventure—cruise a river past the terraced landscape of one of Portugal’s finest wine-growing regions…view a Gothic church with 650 pounds of gold plating…step back in time at Portugal’s best-preserved Roman ruins.

Or stretch out on the sands of the Portuguese Riviera and, atop a mountain in a national forest, embrace Romanticism in a flamboyant palace…sip award-winning wines, dine on fresh fish and aged beef, and marvel at the variety of breads and pastries available in aromatic padarias and pastelarias.

"Even in the tiniest town you might stumble on a former home or factory converted into a museum or exhibit hall,” says Tricia Pimental, IL Portugal Correspondent. “It could cover a craft like lace-making, or a process like the production of olive oil or cheese.

“Culture is everywhere. Speaking of which, music figures prominently in culture. In the most modest of villages, festivals with marching bands and pop singers spring up regularly. At the opposite end of the spectrum there are concerts featuring the likes of Maroon 5 and Aerosmith in major arenas in Lisbon and Porto.

"Health clubs and spas are scattered around the country, in both big cities and rural regions, where you'll also find folks outdoors running, biking, boating, surfing, etc."

"Finding your North American comforts ranges from ridiculously easy to somewhat challenging depending on where you live in Portugal. You don't have to grocery shop in Lisbon, Porto, or the Algarve to find familiar brand names, organic items (called "bio" here), restaurants offering gluten-free options, etc. You do have to work a little harder in the northeast and central zones, but once again, as there are several major supermarket chains throughout the country, it's generally not an issue.”

Costa Rica

“There are several factors working in your favor when searching for your "tribe" when you initially move to Costa Rica,” says Kathleen Evans, IL Costa Rica Correspondent.

“First, this beautiful Central American country has been on the radar for expats for decades. You won't be a pioneer if you decide to move here. That means there are expat communities in much of the country—especially in the Central Valley and the beach areas. All of these people were once new here, trying to learn the system and looking for a social network. So you will find most to be quite friendly and helpful.

“Secondly, the native Costa Ricans (Ticos) are by nature very welcoming. It is not unusual for the new gringo in town to get invitations to the local festival or birthday party. Especially when you are open to speaking Spanish and embracing their traditions.

“The third factor is social media—something that didn't exist for the early expat pioneers. It is easy to join various groups online to learn about all of the upcoming events locally. If you enjoy keeping busy, you will have no lack of entertainment. From volunteer opportunities to listening to live music, and card games to yoga classes, and fundraisers to pickleball tournaments. The expat community likes to keep active. In fact, you may find your social calendar filling up even more than back home!

“If you are a lover of the arts, in Costa Rica you will want to reside in or near San Jose in the Central Valley. This is the epicenter for museums, theater and ballet, art galleries, sports, fine dining, and extreme shopping.”


Malta takes third place with 90 points in the Fitting in and Entertainment category of this year’s Annual Global Retirement Index.

Malta is known for the beautiful Mediterranean Sea, warm and sunny climate, peaceful lifestyle, and rich cultural offerings—a coveted destination for centuries.

"It's super easy to fit into the Maltese lifestyle from day one,” says Kevin Casey, IL Contributor.

“Everyone here speaks good English and the scenery, infrastructure and food scene exceeds expectations. People are friendly, down to earth and eager to show you how to live like a local. And the sunny climate is heavenly—Malta's capital, Valletta, has the warmest winter temperatures of any capital city in continental Europe.

“Entertainment-wise, there's so much going on. You can indulge in everything from opera, rock concerts, foodie festivals and craft beer tastings to boat charters, arts events and a buzzing nightlife. Malta's cafe culture has a distinctly Italian flavor, so prepare yourself for plenty of cannoli, cappuccino, brilliant pizza and fresh seafood—the quality is amazing."


Ireland takes the fourth spot in the Fitting-in and Entertainment category of International Living’s Annual Global Retirement Index this year, scoring 88 out of 100. Known as the Land of a Thousand Welcomes, it not surprising to see Ireland scores highly.

“Getting along well in a new country isn’t just about the cost of living or the climate,” says Sean Keenan, IL Editor. “Those are important, but it’s no use living in a place with perfect weather and low costs if you feel unwelcome, uncomfortable, or just plain bored. Can you go to a movie in English? Is there a diverse choice of restaurants and bars? What about a symphony orchestra performance, or a rock concert by a band you’ve heard of? Can you get the TV channels you’re used to?

“All these are important details—the type that can make or break your time overseas.

“And then there are the intangible aspects of a place. Are the locals friendly and welcoming, or are you just another target for scams and hustles? Do people speak English? Can you meet up with other English-speakers and have a social life?

“When we ran the numbers and weighed everything up, we weren’t surprised by how well Ireland did in the category.

“Famous for both its welcome and for its energetic nightlife, the Emerald Isle is an English-speaking European nation, so you can get involved in the everyday life of the people around you without feeling you’re in an expat ghetto. Join local clubs, societies, chat with your neighbors, and immerse yourself in the community. And don’t miss the chance to pop into the pub for a pint and a chat. Although once it gets started, you might find it hard getting a word in!”

More information on the easiest categories to fit in from the International Living 2020 Global Retirement Index can be found at: Great Places to Retire Where it’s Easy to Fit In

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About International Living

Since 1979, InternationalLiving.com has been the leading authority for anyone looking for global retirement or relocation opportunities. Through its monthly magazine and related e-letters, extensive website, podcasts, online bookstore, and events held around the world, InternationalLiving.com provides information and services to help its readers live better, travel farther, have more fun, save more money, and find better business opportunities when they expand their world beyond their own shores. InternationalLiving.com has contributors traveling the globe, investigating the best opportunities for travel, retirement, real estate, and investment.

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