Should I Retire Abroad?

How do you imagine your retirement from the airline industry? Going to your grandkids’ baseball games and finally renovating your kitchen? Or perhaps you see yourself choosing an exotic country—maybe one of those cities you’ve been flying over for so many years—and retire abroad there with weekly golf games and a more cushioned lifestyle.

You wouldn’t be the only one to fly the coop for the golden years. According to one survey, of all Americans living abroad, almost 25% are retired and 44% would like to stay abroad for the rest of their lives.

So, there’s something to be said for living abroad. But what exactly? Let me break down the good, the bad, and the “mm, it depends on your outlook” categories, and then I’ll let you decide if you want to retire abroad. What it all boils down to is your interest in your future.

 More Bang for Your Buck

Likely the biggest appeal for living abroad, the cost of living is cheaper. How much cheaper?

An old friend lives in Costa Rica in a cozy two-bedroom apartment thirty minutes from the beach and pays $1000 a month in rent.

A client living in Barcelona, Spain shares a two-bedroom apartment with his girlfriend in one of the city’s nicest neighborhoods and together they pay $1300 a month.

A college friend lives in a one-bedroom in a central neighborhood in Paris, France, and pays $1700 a month.

Yep, prices vary a lot. But numbers aside, ask yourself what’s important to you. Do you want art galleries, museums, and a movie theater nearby? Or do you prefer less civilization and more sprawling views of the green countryside or the ocean? You can find both and a range of options between, but figuring out your chosen lifestyle is crucial.

Your Chosen Lifestyle

Then think about what that lifestyle implies. When my client decided to retire abroad in Barcelona, he loves the fact that he doesn’t need a car. Public transportation is efficient and reliable and it saves him a lot of money. If he wants to take a trip, he gets on a train, plane, or rents a car. At the end of the day, it’s still way cheaper than keeping up a car and paying for parking. And the great thing about trips in Europe is the distances and the differences! A two-hour flight or less lands you in a different land with a different language and different customs.

On the other hand, my friend in Costa Rica couldn’t enjoy her life without her car. Gas may not be cheap and cars are more expensive down there, but she sees it as a small price to pay for the kind of life she wants. As far as traveling, there aren’t huge changes in Latin America from one country to another, so her trips are more centered around exploring new beaches and national parks within Costa Rica.

What appeals more to you? Figuring out the answer to that question will narrow down your options to a more manageable list.

New Cultures, Different History, Different Language

Right, you’re no stranger to different cultures. After all, you’ve worked for years in the airline industry that puts those cultures within our reach. But living somewhere is a whole lot different from visiting there as a pilot, first officer, or captain.

I can’t say I could ever see myself living in Paris, but for my college friend, that was her dream. She loved the history, the art and music scene, the food. She’s now been there for three years but will be moving to Amsterdam at the end of the year. Why? The language that had once seemed so beautiful to her ended up making her feel like an eternal outsider who will never be able to fully understand everything that’s happening around her. And, well, let’s just say Parisians aren’t known for their hospitality, either.

But contrast the infamous coldness of Parisians to the well-known hospitality of the Portuguese or Mexicans, and you’ve entered new worlds. Of course, knowing the language is going to make a world of difference when you retire abroad, but so will the environment in which it’s spoken.

That brings me to my next point …

Health Care

I know it’s much more fun to talk about lifestyle and cities, but this point can make or break your utopic retirement abroad. But I have good news—health care abroad is almost always cheaper than here at home.

Of course, quality is going to vary, and even more so when you take into account your location within a country. Living by the beach you’re going to have to go farther to find doctors, equipment may not be as new, and wait times may be longer. But if you choose a more populated area, all that will improve.

Latin America and Asia are popular destinations for medical tourism. (Yes, medical tourism is a thing if you haven’t heard of it.) You can find hospitals accredited by Joint Commission International (JCI) that holds medical facilities up to demanding standards. Search a country’s hospitals here to find out which are certified with JCI.

Many countries have a public health care plan and private plans. Private plans usually range from $50 to $100 a month and are often free of the deductibles and copayments that we have come to know so well here at home.

Patience vs Quality and Cost

But naturally, it’s not all roses. A former teacher in Madrid, Spain, had a bad spell that landed her in the hospital two times in the same week. Crippling back pain sent her to the ER and then two days after she was back home, a near stroke sent her back. She was admitted, but the doctors were backed up and though they took her MRI on Friday, they weren’t going to be able to read it until Monday. This meant she had to stay in the hospital over the weekend simply because no doctor could read her MRI until then. While this situation would frustrate any of us, her growing impatience was quelled by the quality attention she received that Monday and the nonexistent hospital bill upon her departure. She pays $70 a month for her insurance, and that week she didn’t pay a penny. Or céntimo, as they say in Spain.

Will your health care experience require patience and flexibility? Of course. But if you do your research and choose accordingly, you may end up being pleasantly surprised.

Residency / Visa Situation

The good news is that retirees are quite welcome in many countries abroad. On the whole, Spain and Portugal tend to be popular options in Europe, while countries in Asia and Latin America populate the rest of this 2019 list of the world’s best places to retire.

And this is where that mandatory retirement and years of service as an airline pilot come in handy! Show your savings and provide documentation of your retirement fund through American, United, or Delta (or any other retirement fund, for that matter) and things get a lot easier.

Or maybe you’re looking into buying property in your new country? Great! Countries often expedite the residency process for foreigners buying property there.

In most countries, you’ll have to renew your visa every one or two years, but usually, after about five years, you can apply for permanent residency.

Exchange Rate & Banking

You’ll likely get your pilot retirement disbursed in USD. That may or may not be favorable with the foreign currency that you’d be dealing with on a daily basis.

Some people who retire abroad open accounts in USD in their new countries to mitigate losses with the exchange rates. When the exchange rate is good, they transfer money from a dollar account (in the U.S. or in their new country) to their account in the local currency. Bank accounts in USD in Latin America are not that uncommon, for example, but those bank accounts may come with a fee, especially when you hop over the Atlantic.

Another point worth considering is the ease and cost of international transfers. Ex-pats often transfer a few lump sums a year to keep costs down, but even beyond that, plenty of international services promise to transfer your money for less.


You can’t escape Uncle Sam, even if you’re living abroad! As a retired pilot, your taxes will hopefully be pretty painless.

As a resident in your new country, if your income comes from abroad (as in your retirement from Southwest or Delta coming from the U.S.), then you likely won’t even have to file taxes there in your new country of residence. This varies from place to place, however, so be sure to check the specifics.

If for some reason, the retired life isn’t for you and you just have to work in some capacity in your new country—we do come from a country of workaholics, after all—then any income earned while abroad can be excluded from your U.S. taxes if you can prove you reside in that foreign country and you’re not making exorbitant amounts of money.

Ready to Retire Abroad?

So, how’s your list of pros and cons to retiring abroad measuring up? Still dreaming of weekend trips to exotic locations and more spending money in your pocket? Are you ready to board that plane as a passenger and take off on a new trip?

I’m guessing you’re already attracted to adventure or else you wouldn’t have become a pilot in the first place. It’s in your nature to explore, so why not start there? Explore. Maybe you already have some countries in mind, so take a trip and visit them.

Visit those countries and find out the answers to some of the questions and issues I’ve posted here. Start narrowing down your list. Chat with other ex-pats who have chosen to live in that country (there are Facebook groups for everything these days!) and see what they have to say. How much of the foreign language will you need to know? Look at everything from traffic and public transportation to the food in the supermarket. (Your diet will change, I can guarantee it. But that may be a good thing!) Pay a visit to a bank or two and ask about international transfers and accounts in USD. Ask yourself how far away from home you want to be. If you have family and friends you’d like to visit or have come to visit you, then Latin America may be a better fit over Asia. The more you know, the better you’ll feel about your ultimate decision.

And when you do make that decision to retire abroad, I’d love to hear about it!

Both adventure and caution have framed your career as a pilot. Why shouldn’t they frame your retirement, too?

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