The Best Places to Live as a Remote Worker

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Posted by The Savvy Retiree on December 16, 2020 in Live Better

“Where’s the best place to live as a remote worker?”

I regularly hear some iteration of that question from friends and acquaintances, so I thought I would answer it today in light of new research out of Upwork, the freelance website I regularly write about. The company surveyed a bunch of Americans and concluded that about 11% of U.S. households will be moving in the coming year to pursue better job/lifestyle opportunities. That’s a relocation rate about four times higher than normal, according to Upwork’s in-house economist.

Upwork’s research underscores what I started writing back in the earliest days of the coronavirus lockdown: The U.S. is rapidly moving away from cubicle culture and toward a work-from-home/work-from-wherever lifestyle.

Already, that relocation binge is underway. The Dallas Federal Reserve published research just last month showing that COVID-19 “had reduced demand for housing” in and around big, dense cities and neighborhoods across the country. It’s clear as well that many Americans are looking to take their life overseas. As I’ve noted several times, New Zealand is seeing record interest from Americans who want to emigrate. Numerous Caribbean islands are offering one- and two-year work visas. And International Living has seen search demand for moving overseas explode higher.

But none of that answers the bigger question: Where’s the best place to live as a remote worker?

So I thought I would give you my personal thoughts on that.

As you might know from previous columns, I am a global wanderer who has so far set foot in nearly 70 countries across all the habitable continents. As part of those travels, I have regularly asked myself: “Could I live here? Would I want to live here?” As such, I have a particularly broad base of boots-on-the-ground knowledge about a lot of countries and even more cities.

And that’s what I want to share with you, if for no other reason than to get you thinking about your own wants. This is, obviously, entirely personal and it’s based purely on the places I have visited (so if I leave off great places, it’s because I’ve not been there and I can’t comment on them). 

Moreover, my definition of what makes a place livable is unique to my worldview. I want cosmopolitan cities, places with high energy, that are beautiful and walkable (I despise traffic). I want to stroll at night and pop into cafés and restaurants. I want to feel life around me, not desolate streets waiting for the sunrise to rejuvenate them again.

That’s why you won’t find a place like Auckland, New Zealand, on my list. It’s a truly lovely, coastal city. However, (and sorry, Kiwis) the city rolls up the sidewalks at 5 p.m. every day. The center of the city is just dead in the evening. That’s not my ideal.

All that said, here’s where I tell my friends and acquaintances to look (and let me warn you that I like four seasons, so you won’t find idyllic and tranquil beach cities or warm-weather destinations on my list):

Prague. I live here. It’s a truly beautiful, livable, affordable, human-scale European cultural capital. 

Singapore. A bit expensive, yes, but a wonderful city with the best food on the planet (a mélange of all of Asia and India). Hot and sticky 365 days a year, which undermines my four seasons assertion, but I can’t help but love everything Singapore is.

Lisbon. A coastal European capital that, while certainly not off the beaten path, is not overrun like Barcelona, Paris, and Rome. It’s warm. The food is great. The street life is active. The scenery is classically European. My favorite city in the world.

Punta del EsteUruguay. So quiet. So tranquil. Most of the year, this beach town feels like a mid-sized American city in terms of amenities, yet it’s home to about 20,000 people. They even turn the traffic lights off. In the summer, it transforms into the South American Riviera, a party capital for 500,000 people.

Dublin. You just gotta love the Irish. The accent. The charm. The warmth. The lamb stew. The Smithwick’s beer and Bulmers cider. The ambiance. The scenery top to bottom, east to west. They’re modest about it, but the Irish know they live on a magical island.

Istanbul. An odd selection for some, but a city that, because of its mix of Middle Eastern and European culture, feels more exotic than anywhere I’ve ever been. Fabulous food. Beautiful scenery. Safe. Affordable.

Moscow. Again, probably a weird selection for some. But it’s a rambunctious, vibrant city that feels and looks like an odd mashup of Tsarist Russia, Communist Soviet Union, and futuristic Asia. Cold as hell in the winter. Hot in the summer. And just an energetic place.

Tallinn, Estonia. If Game of Thrones had been set in the 21st century, Tallinn would be King’s Landing—the center of the empire. It’s a small town, truly Old World, but one of the most forward-thinking, technologically advanced cities in Europe.

Vancouver. The crazy-expensive love child of Singapore, Hong Kong, and San Diego. With the parks, the evergreen forests, the mountains, the bay, the skyline…well, just the most picturesque coastal, metropolitan city in the world. And Canadians are just so polite.

Barcelona. My second-favorite city in the world. The food and wine—it’s just a hair’s breadth behind Singapore. The Spanish culture is warm and inviting. It’s right on the Mediterranean, so it’s warm much of the year, but winter temps still dip into the 40s and 50s.

Finally…Tokyo. Another expensive place, no doubt. But Japanese culture is fascinating. The city is beautiful, energetic, and crowded. And the country, despite its geographic size, has everything from tropical beaches to Olympic ski resorts to serene, forested hot springs. And with bullet trains, it’s easy to be-bop around the country relatively quickly.

So, there you have it: Jeff’s list of great places to live in the world. Like I said, it’s an entirely personal list, and I know I’ve left off other wonderful cities. Still, it’s a starting point to get you profiling yourself. What do you want in a city? That will inform your choices if you’re considering pursuing a life outside the U.S.

By Jeff D. Opdyke