The 5 Most Overrated Countries for American Expats

Ranked by the people who actually left them.

Every country on this list is beautiful. Every country on this list is somebody’s happy ending. I want that said before the hate mail starts.

But I don’t rank countries by beauty. I rank them by the gap — the distance between what the internet promised and what my case files recorded after year one. The wider the gap, the higher the ranking.

By that measure, these are the five widest gaps in my files. Number one will make some of you close the tab. Read to the end anyway; the country everyone should be talking about instead is at the bottom.

5. Dubai — the city that works perfectly and owes you nothing

The pitch: no income tax, everything gleams, packages arrive in two hours, crime is a rumor. For a certain kind of burned-out American professional, Dubai looks like civilization with the bugs fixed.

And it delivers. That’s what makes it interesting: Dubai is the only country on this list that keeps every promise it makes.

The problem is the promise it never makes. There is no version of this story where Dubai becomes yours. No realistic path to citizenship, residency forever tied to your visa status, a social world made of other temporary people. A 38-year-old consultant in my files described her fourth year there: “Everyone I know is on a two-year plan that’s in year six.” Nobody plants anything, because everyone is officially leaving.

Dubai is a business-class lounge the size of a city. Lounges are wonderful. Nobody lives in one — they wait in them.

Overrated for: anyone who wants a home. Correctly rated for: anyone with an exit date and a number in mind.

4. Costa Rica — paradise, priced accordingly

Costa Rica invented the modern expat dream and never let anyone forget it. Pura vida, monkeys in the yard, the retiree in the hammock who “lives on nothing.”

Here’s what the hammock photo doesn’t caption: that retiree bought in 2009. My recent Costa Rica cases run budgets that would raise eyebrows in Florida — imported goods taxed into luxury items, San José-area rents chasing US suburbs, a car costing half again what it costs in Texas. One case, a couple from Georgia, left after their grocery bills exceeded what they’d paid in Atlanta. For groceries, in the country they moved to because it was cheap.

Costa Rica isn’t a bad country. It’s a 1999 price tag on a 2026 shelf, sold by an industry — relocation tours, YouTube channels, seminar cruises — with no incentive to update the sticker.

You’re not buying paradise. You’re buying the memory of what paradise cost twenty years ago, at today’s prices.

3. Italy — the fantasy with a waiting room

Nobody moves to Italy. People move to a montage: the Tuscan light, the €1 house, the nonna teaching you to fold tortellini.

Then the montage ends and the line begins. My Italy files read like a bureaucratic hostage log. The residence permit appointment scheduled four months out, then rescheduled. The codice fiscale needed to get an apartment, the apartment needed to get the permit, the permit needed for everything else — a circle my cases learn to describe with dark laughter. A retired architect from Colorado renovated her €1-adjacent house in Sicily beautifully. It took four years. The permits took five. She lived the fantasy eleven months and spent the rest in the waiting room around it.

The cruelest part: Italy punishes exactly the people it attracts. Romantics. Planners die there too, but romantics arrive with no armor at all.

Italy is a masterpiece behind glass. You can visit the masterpiece. Moving into the museum is a different transaction, and the museum staff did not vote for you to be there.

2. Bali — a two-week life, extended indefinitely

Bali produces more relocation content per square kilometer than anywhere on earth, and it is all technically true. The villa does cost $900. The smoothie bowl is photogenic. The coworking space does overlook rice terraces.

What the content can’t show you is duration. Bali is engineered — spiritually, economically, algorithmically — for the two-week version of you. The two-week you doesn’t need a visa strategy that resets like a video game every few months. Doesn’t sit in Canggu traffic that has become its own genre of complaint. Doesn’t get the scooter injury that fills the group chats, doesn’t discover that “community” here means people who arrived after you and leave before you.

A 29-year-old designer in my files did the math on her third year: eleven visa runs, four housing moves, one crash, zero friendships older than eight months. Her line stayed with me: “I have the best life in the world, two weeks at a time.”

You didn’t fall in love with the island. You fell in love with the version of yourself that visits for two weeks — and that person doesn’t pay for visa runs.

1. Portugal — loved to death

I know. I know. Put down the pitchfork and hear the argument.

Ten years ago Portugal was the answer: affordable, gorgeous, safe, tax-friendly, the golden visa humming, Lisbon still a local city with local prices. Every one of those pillars has since cracked, most of them under the weight of the people this dream attracted. The tax regime that lured foreigners: closed to newcomers. The golden visa’s property route: gone. Lisbon rents: up so far that locals hold protests about them, in a country where salaries never moved. The bureaucracy, always slow, now runs through a backlog measured in years.

None of that has reached the content machine, which still sells 2016 Portugal at 2016 enthusiasm. So my newest Portugal cases arrive into the widest expectation gap in my files — priced like California, welcomed like a symptom. One family from Seattle was told by their Lisbon landlord, politely, that he was choosing between them and a Portuguese nurse, and the nurse couldn’t match their offer, and he wanted them to know what their money was doing. They stayed. They think about that sentence weekly.

Portugal isn’t overrated because it got worse. It’s overrated because it got popular, and popularity is the one problem a beautiful small country cannot fix. The dream ate the thing it was dreaming about.

The mirror, for all five: the country was never lying to you. The version of it that fit in a YouTube thumbnail was.

The one nobody ranks

Since I’ve now insulted five national fan clubs, let me end by starting a different fight.

The most underrated country in my files is Uruguay. Nobody makes content about it — too calm, too normal, terrible thumbnail material. Stable democracy, legal path to citizenship an American can actually complete, mild politics, beef and beaches, Montevideo dull in the way Zurich is dull. My Uruguay cases have the least dramatic stories I collect, which is precisely the point. Nobody’s filming there. That’s how you know.

Drama is a cost, not a feature. The countries that photograph best tend to charge for it later.

So: which one did I get wrong? The comments are open, and yes, I already know about your cousin who’s thriving in Lisbon. Tell me anyway.