The Surprising Truth About My New Hometown in Portugal

Apparently, I’ve moved back to America.

I officially started my new life in Portugal this week. After nearly five years of living and working in Prague, I’ve grabbed one of Portugal’s new D8 Digital Nomad visas and have relocated to the Iberian Peninsula with my family.

As I’ve mentioned in previous dispatches, we’ve chosen to live in Cascais, a highly popular beach town about an hour west of Lisbon. I call it a town, but having spent the last several days driving around to buy furniture and whatnot, I think “town” is stretching the bounds of that definition. It’s an overgrown village… in the absolute best possible way.

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Entirely walkable. Truly lovely and picturesque. Tree-lined residential streets so perfectly homey that, while we were driving down one, Yulia, my wife, announced unexpectedly, “I want to live here! Right on this street!”

I also want to clear up—or at least recalibrate—a description I offered in a recent dispatch. I compared Cascais to Southern California meets Baja California and Northern Arizona. But that was based entirely on days of relying only on my feet to move around the area.

The rental car has expanded our exploratory zone and now I will say that the area writ large is coastal Southern California, replanted in the Rocky Mountain foothills.

Deep ravines. Undulating hills and mini-mountains, covered in a carpet of pines, sycamores, and eucalyptus, among a litany of other tree species.

In short: A wonderfully picturesque corner of the world. (I want to note that lots of Europe is equally picturesque in different ways, which is one of the reasons I’m so smitten with this continent.)

At this point in our dispatch, I’ve totally lost the original plot: That apparently, I’ve moved to America. So, let me explain that in three words: Americans. Are. Everywhere!

Restaurants are packed with Yanks. An optician I visited to replace glasses I broke during the move had an American couple buying sunglasses. The mall we visited for some homewares shopping might as well have been in Any City, USA. You’d recognize 75% of the signage, and at least 25% of the background chatter I heard was American English.

These Americans in stores like Zara Home were clearly shopping for goods for their local house. It’s not like you pop into Zara Home in Cascais because you wanna bring souvenir bath towels back to the U.S.

Given the ambiance, the near-constant sunshine, and mild temperatures (60s at night, mid-70s and breezy during the day), I totally get why so many Americans—particularly Californians—have replanted themselves in coastal Iberia. Having lived in both Laguna Beach and Long Beach, California, I understand the magnetic draw Cali natives feel here.

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We popped into a Japanese restaurant that specializes in grilling various chicken parts (my favorite eatery so far) and the waitress told me they see a constant stream of Americans. Many are tourists, obviously, but this is a restaurant located off the typical tourist path through Cascais, “so a lot of them are Americans who live here now. You’ll run into them—seems like they’re everywhere.”

In my previous dispatch about the week I recently spent shoring up apartment and banking details, I said that Americans in or near retirement should give Cascais consideration as a place to live far more cheaply than in the U.S., but at an elevated standard of living. I’m gonna double down on that comment.

I keep reading one story after another about Americans who have little to nothing saved for retirement, and are preparing mentally for a drastic downshift in their lifestyle. If I can convince you to even consider briefly the idea of ramping up the quality of your life by moving to Portugal, then my job today is a success.

You might not immediately act on my recommendation to move to Portugal, and I would not expect that.

But maybe I can plant that little seed—the “what if” or the “hmmm, I wonder…”

Frankly, that’s been my goal over the last many years—to do what I can to plant those seeds.

It doesn’t have to be Portugal or the Czech Republic—those are just the examples from my life I use to illustrate the possibilities. It could be Spain. Or Costa Rica. Or Thailand… or Greece, Uruguay, Italy, France, or Panama. Anywhere that excites you, really. (For expert advice on finding your dream overseas destination, join me and International Living’s other experts at our upcoming conference in Denver. Details here.)

The opportunities to upgrade your lifestyle, your happiness, and your financial security exist all over the world.

Pursue that dream and you, too, could be one of the Americans that causes a writer like me to think he has accidentally moved back to the States because he’s surrounded by so many expat Yanks living their best life yet overseas

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