Editor’s Note: This story originally appeared on Live and Invest Overseas.
Shopping the globe for the golden stretch of sand or the jaw-dropping ocean view with your name on it?
I can imagine worse ways to spend your time.
Still, I understand that considering the whole world at once can feel overwhelming.
That’s why we’re here … to help you compare, contrast, consider, and filter your options.
Where best could you reinvent your life overseas right now? Here you go … to get your imagination flowing … my short list … the five countries I’d suggest you put at the top of yours.
1. Panama
Comfortable, convenient, developed-world living with many lifestyle options along both Pacific and Caribbean coasts
World’s most generous retiree visa program
Lots of American influence and big, established, and welcoming expat communities
I was the first to shine a spotlight on Panama.
That was nearly 30 years ago.
Since that way-back-when recommendation, I’ve lived in Panama, raised my son here, launched a business here, and made 13 property buys, from buildings to renovate and pre-construction rentals to land for banking, a teak plantation, and the biggest investment of my life at Los Islotes on the country’s Veraguas Pacific coast.
I know Panama. And I’m more bullish than ever on the prospects for this little isthmus. It is the best place in the world to think about spending your time and your money today.
It’s the world’s top retirement haven … a tax haven … a stable investment market … and an entrepreneur’s playground.
This little country caters to North American retirees with a famous Red Carpet suite of residency benefits that includes discounts on everything from utilities to movie tickets, and it’s a great place to raise a family.
I make every one of those statements based on personal, firsthand experience over decades.
And I tell you now that whatever your age, your budget, your circumstances, or your objectives, you should be looking at Panama. It’s the world’s do-everything haven.
2. Portugal
8-time winner of our annual Retire Overseas Index
Easy and affordable EU residency
English spoken everywhere in certain coastal regions
If you lean more toward the Old World than the New, I recommend a close look at Portugal.
This is one of the world’s safest, most peaceful countries, and it’s as turnkey as Europe gets if you’d like to establish permanent residency.
Understandably, Portugal’s popularity has expanded dramatically in recent years. The costs of living and of buying property have risen as a result, but this remains one of Europe’s most affordable escapes.
The Portuguese are gracious and unassuming and speak English at a high level. In my experience, they’re very good company to keep.
Their modern culture is eclectic and innovative, producing forward-thinking social policies and unique styles of fashion, music, gastronomy, and art. Your life here would be rich and satisfying.
3. Dominican Republic
Quintessential Caribbean beachfront living
The best-value island lifestyle in the region
“Red Carpet” visa options for both retirees and entrepreneurs
Perhaps your go-overseas dream is all about white sand and swaying palm trees. Fair enough. For some, nothing but the Caribbean will do.
The DR is quintessential Caribbean, a sand-fringed island nation offering the best values in the region.
This tropical paradise also boasts one of the best residency and citizenship programs available today, including a Red Carpet welcome for North American expats that includes tax waivers of up to 100%.
4. Mexico
Dozens of beach town options along both Pacific and Caribbean coastlines
Welcoming and accessible, with more North American expats than anywhere else
Easiest residency requirements for Americans
Over the past four decades, Americans and Canadians have voted Mexico the world’s number-one place to enjoy expat life in the way that really counts. They’ve packed up and moved there.
This country is home to more expats from up north than any other — at least 1 million or as many as 2 million, depending on who’s counting. This shouldn’t surprise anyone. It’s easier for an American or Canadian to get to Mexico than to any other country.
Mexico is accessible, affordable, and home to an array of diverse lifestyle options … from its famous beaches (both Pacific and Caribbean) to colonial mountain towns.
North Americans looking to start a new life in a new country primarily seek three things: warm weather, beautiful beaches, and a low cost of living. Mexico competes handily in all three categories.
One of the country’s other advantages for expats is its familiarity, from its administrative set-up (the Mexican government is a stable democracy, with executive, legislative, and judicial branches functioning in a similar way to those in the United States) to its big-box stores.
If you’re itching for an adventure in a foreign land that’s not too foreign, Mexico could be your best fit.
While the cost of living is not as cheap as it was in the 1970s when Americans began migrating here in volume, it’s still a global bargain.
Your budget will depend on where in the country you choose to live and how you live, but even a modest budget can buy a comfortable life some places. Less developed areas are more affordable than well-established expat havens like Puerto Vallarta.
5. Cyprus
English is spoken widely
The warmest island in the region, with 340 sunny days a year
Most affordable beachfront property in Europe, starting at just $100,000
Cyprus is one of the Mediterranean’s most rewarding yet unsung outposts. It’s got the great weather, the beautiful beaches, and the enviable lifestyle the region is famous for … all at a fraction of the price tag along better-known Mediterranean coastlines.
Furthermore, nearly 10% of the population, more than 100,000 people, are foreign retirees or expats. Americans are just beginning to learn about Cyprus, but the island has long lured the British.
Here’s something you might find surprising about me. I have no sense of direction. I can get lost in a big grocery store.
Maybe that’s one reason Kyrenia is my favorite spot in this part of the world. Hard to get lost here. The mountains are always to the south, the sea always to the north. I’ve found that you can count on spotting one or the other before too long.
With a long and storied history (the city was founded by two veterans of the Trojan War), Kyrenia is the tourism capital of North Cyprus. With its ancient harbor and seafront castle, the old town is typically Old World charming.


















