How to Retire at 50 pt. 3: Our Top Three Retirement Locations

Now that we got the hard parts out of the way for “How We Intend to Retire at 50;” and “What to Consider Before Retiring”, the next question is “Where to Retire?”

While retirement seems miles away, my wife and I daydream about our exit strategy. From the freedom from deadlines, managing up and down, and stressing out about money (kinda), we are ready to trade for hobbies and adventures.

According to the U.S. Social Security Administration, roughly 760,000 Americans have retired overseas. Of these, 60% retire to Mexico or Canada. This makes sense due to proximity. 38% opt for their extended stay in Western Europe. Fewer jump for the opportunity to live in Southeast Asia. No matter where you end up, living overseas is more cost-efficient than staying in the U.S. This is especially true for the curious and adventurous types.

Former U.S. residents say it offers a solution to soaring costs of living and health care in the United States. Many retirees are looking to explore new cultures. Others reflect on socioeconomic issues such as growing political dissatisfaction, the widening wealth gap, safety concerns, workload burnout, and food quality. While this doesn’t mean that the rest of the world is a social utopia, some are seeking a fresh start.

The last 40 years have opened up the world. After seeing parking garages and shopping malls, my wife and I are looking to see what the world has in store. See what I did there? It was a well-traveled pun. Guess I need to stay super serious for the next part.

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Retiring Abroad is not for Everyone

If you get uncomfortable with new places, foods, and languages; this might not be for you. Additionally, if you are not into walking; you have been warned. To survive globally, you have to get comfortable with being uncomfortable. It’s a growth thing.

With that said, retiring abroad is not for everyone.

There are pros and cons to everything. In the last few years, I’ve watched social media influencers tout living abroad as the next best thing, only to end up lambasting Spain’s midday siestas. I’m not even making it up. There’s an influencer out there who hates siestas. Proof that cultures and temperaments vary.

Most countries operate on a slow and steady approach. There is a greater appreciation for long conversations and even longer dinners. This is where the bottle of wine comes in handy. It’s the vibe.

I find that most countries closer to the Equator, move slower. My undereducated guess is that since the sun beams brighter, it limits your range at the risk of dehydration. The further away from the equator, the quicker people move from one place to the other to avoid the cold. After a couple of centuries, locations create identity.

There are other locations where picket pockets roam like the movies. I was yelled at in Amsterdam for daring to ask for a plastic bag after we purchased a camera. The cashier grew suspicious about what we would do with the bag. We eventually got the bag but the interaction was strange. They take recycling to a new level; I think he believed we would throw it out the window somewhere. Some people take cleanliness to a new level. In Japan, out of respect, they might not look you in the eyes. One traveler noted that no one wanted to talk to her in Paris. But then again, it’s Paris.

Venturing into the unknown isn’t just a change of scenery. Additionally, time will move differently on retirement versus a two-week vacation. What you might find thrilling on a quick trip with (seemingly) unlimited funds, might be ‘trifling AF’ after waiting 4 months on your Italian $1 home remodel.

In the end, living internationally is predicated more than the tourist hubs. It’s about 30 mins to 1 hour away from those hubs. You have to dig deeper and learn how the locals move. As time goes on, you have to make new friends and networks. Both of which may be harder in retirement.

What to consider?

So, what should you consider when deciding to live abroad? It comes down to you. Some of the easy and popular questions are; which countries are the cheapest to live in? What’s the local quality of life? The best weather? Which has the lowest crime rate?

Each question is a great start. There is nothing wrong with crafting your destination with this in mind.

More sophisticated planners also consider Visas, fees, and limitations for non-citizens. Some countries have an income requirement and more red tape. You will have to remember to file your U.S. tax return. Spend some time researching. You can even find a Facebook social group for tips and tricks. When you get there, consider finding some form of employment. Teaching English might be a good fit. Becoming a translator or local tour guide. Or just double down on a language immersion course. It’s important to find any reason to get out and mingle.

While I wasn’t able to find her by name, this lady covers the experience of moving to Asturias, Spain quite well. I never heard of the place but the pictures are amazing. Check out the video below.

It’s all about Connections!

Beyond the affordability issue, my wife and I want a hub with easy connections (i.e. flights in and out).

Some of the best locations that I’ve found are not the tourist centers like Paris. While the Eiffel Tower is nice, a lesser-known city like Marseilles has better views and likely better prices. With that in mind, flights may be harder to come by. In that case, my wife loves the option of going by train.

For example, you can catch a cheaper flight out of Paris or London, depending on which city you are in by simply connecting by train.

In 2019, we flew into London, took a train to Paris, and stopped for a few days. After that, we boarded the train again to Brussels and then Amsterdam. All to train and fly back out from Amsterdam to Rome. It’s all about connections.

This works best if you are traveling light, backpack, and carry-on. You can travel heavier. I’d recommend adding more time to your transit and additional funds. The best part is the cost, European trains are fast, efficient, convenient, and cheaper.

In retirement, I would like seamless access if we need to hitch a ride to the US to visit family. Or better, if they want to travel to meet us. Living in a remote space, two to three hours from the nearest airport won’t cut it. This also makes it easier on guests.

The final connection is all about the Data. Internet connectivity is worth its weight in gold. Feel free to check out the median country data speed to see where your preferred destination ranks.

Health Care and Travel Insurance!

For those aspiring to live abroad, I would recommend researching global health insurance as you settle into a new space. Obtaining universal healthcare is crucial. It provides comprehensive coverage while easing the financial burden of medical expenses.

Over two-thirds of the countries currently offering digital nomad visas have universal healthcare. Germany, Spain, and Malta rank as the top 3 European Countries For Expat Healthcare.

Get your medical (and will) documents in order. Since my wife has Diabetes Type 1, she is the queen of all our medical documents. Also, try to invest in a digital lockbox since paperwork can get lost. Prices for insulin and other medicine tend to be cheaper but you will need to translate. Countries that we’ve gone to like Canada, Mexico, and Italy made the process easy. The second piece to this is travel insurance. It can safeguard your nonrefundable reservations and reimburse you for any unexpected emergencies.

Nerdwallet.com listed the top 9 travel insurances.

Allianz Global Assistance is the most recognizable for me. It offers affordable coverage for annual or multi-trip travel. Allianz’s multi-trip policy covers trips up to 45 days in length. These policies cover the cost of illness, delayed arrivals and departures, baggage losses, and even unforeseen pregnancy complications.

“Location, Location, Location!” To Retire to?

As they say, it’s all in the location. We have three locations in mind. Each has its charm but in no order; Portugal, Brazil, or Spain. The reason that they made the list, is the food. I could not retire in a place where I didn’t get fresh fruits, seafood, or simply great dishes.

Although I rank Haitian (Creole) cuisine at the top, followed by Cuban food; my wife and I became fast fans of Portuguese food.

It’s a great blend of flavors with a punch of color. Love my food with an African influence. Follow that up with some drinks, it’s worth the price of admission every time.

Additionally, the views help. You can give us the rooftops of Lisbon with the blue tiles, the mountains and beaches of Brazil, or the Moorish-inspired Andalusian influence in Spain.

As long as I’m not looking at the parking lot, I’m happy.

Retire in Brazil if you are looking for a low cost of living, beautiful beaches, vibrant culture with lively festivals, and affordable property options. Settle in Spain for its high-quality healthcare system, rich culture and history, beautiful scenery, and a laid-back Mediterranean siesta lifestyle.

But for us, we will likely retire in Portugal

Portugal offers retirement options with its affordable living and welcoming visa policies.

While the environment may vary from city to city, there is a high quality of life with accessible healthcare. The quick travel to other countries adds to its versatility. We’ve been to the south of Portugal twice so far with a trip north set for mid-2025. From castles, forts, wine, vibrant cities, the Algarve, and great transit, we really can’t wait to stay longer than two weeks.

With that said, I would not mind living in Búzios, Brazil. The best part and the only drawback is its remote nature. Might need to consider a vacation home. One can dream.

We’ve come to the end of the journey, feel free to check out the video below from Marriage, Kids, and Money of a couple who isn’t retired just yet but decided to move to Portugal.