A Navy SEAL Story of Becoming an Expat in Lisbon, Portugal

“Why did you move to Portugal?”

It’s complicated…

I get asked this question all the time and this is my attempt to explain how and why my move happened.

Like many people, I was personally and professionally upended by the COVID Pandemic in 2020.

At the time I was living in the American territory of San Juan, Puerto Rico with a home office in Manhattan’s Flatiron District.

Life was good until it wasn’t.

I remember my last week being on campus at Harvard Business School in Boston and noticing everyone in the class started getting sick—one classmate was hospitalized.

Because we had an international cohort of business owners, the news and rumors started flying, and it was clear this was not “the flu.”

I had accepted an invitation to visit a classmate in Moscow, Russia, so after packing a bag in New York, I boarded an Aeroflot flight for the Russian capital.

The last time I’d been to Moscow was for World Cup a few years earlier, and I was looking forward to visiting again. My friend had threatened to take me to a traditional banya, one of the oldest in Moscow.

I had no idea what was coming for me with COVID.

I had rented an incredible apartment in one of the better neighborhoods near Patriarch Ponds, a trendy part of town with great places to eat.

My friend met me the next morning with his two sons and his private driver, and we were off to an incredible experience of a traditional lunch, vodka, more vodka, and then being heat tortured (the ice bath after was amazing), and beat into submission with Birch branches as the banya workers shoveled wood into a raging fire that would make Mordor jealous.

The heat was super intense but felt so good afterward.

Sandunovsky Banya: The Most Spectacular Bath House in Moscow

(Photo: Sandunovsky Banya, Moscow, Russia)

Then the World started to come to a halt, one country at a time.

President Trump announced a pending flight ban, and shit started to get serious, but Moscowvites were oblivious at the moment. I knew I had to get back to America soon, but I also wanted to milk a few more days of freedom because I could tell things were about to get serious fast.

A few days later had me on a flight back to New York’s JFK and one of a handful of travelers on the plane with a very nervous crew.

Landing in JFK was like stepping onto the set of, The Walking Dead. I was literally the only person through security at JFK as I boarded a flight to San Juan.

Strange times…

Fast forward almost a year, and I sold my house furnished, packed up my NYC apartment and grabbed a roll-aboard and backpack, and traveled all over for just over a year.

It was an incredible experience, and flights were insanely cheap, and airports were desert landscapes for me and my fellow COVID travelers.

Bogota, CDMX, Tulum, Cabo, Milan, Venice, Capri, Budapest, Zurich, London, and towards the end of my travels, Lisbon.

I heard great things about the small country of Portugal. If you mashed Napa Valley, Big Sur, and Santa Barbara together with better beaches and better food, you’d have Portugal.

Lisbon was a thriving international city where a few minutes outside the capital, you could find yourself on a beach by yourself.

It wasn’t love at first sight, but close to it.

I had a few friends who’d moved to Lisbon and raved about it. I was starting to see why.

An incredible dinner out was $20-30. Airport Uber to the center was $8, and the weather…just incredible.

I was hooked and started digging into how an American could live here legally and made the decision to move.

My top reasons: