How to (Fall in Love and) Move to Portugal

One morning in 2016 I woke up in Portland, Maine, and thought, “Why do I live here?” I’d recently been divorced (for the second time), both my parents had passed, my mom only a few years before, my daughter was living across the country in San Francisco, and my two brothers were in different states.

And here I was in the state where I was born, approaching retirement age, never having lived anywhere else. It dawned on me that morning that, except for a few close friends, I no longer had any real connections holding me back from living wherever I wanted.

For so many years, my job, marriage, and family kept me shackled to Maine. But now, suddenly, I was unencumbered, unattached, free to go wherever I chose. I thought, “I’m not getting any younger, and before I check out, I need to experience another venue.”

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So, for a variety of reasons, most having to do with connections and job prospects, I chose Washington, D.C. I put my condo on the market, made a tidy sum when I sold it two weeks later, packed my belongings into a U-Haul, and departed for the nation’s capital. I stayed with a cousin in Alexandria for a few weeks until I found a comfortable apartment in Woodley Park, a bustling neighborhood near the zoo in Northwest D.C., and landed a well-paying consulting gig with the Federal Highway Administration.

I didn’t know if I’d like living in D.C, but it turned out I did. I liked the big city, the vibrancy, its culture, and even the politics, which is to D.C. what my hometown’s paper mill was growing up in Maine, its major industry. Get-togethers in D.C. were like meetings at the United Nations or an Up With People concert with folks from all over the world — China, Poland, Nigeria, Hungary — a long way from the homogenous, mostly white land of Maine.

I spent my time exploring the many museums, going to Nationals’ baseball games, and enjoying the nightlife and restaurants. I met a lot of cool people, started a Bob Dylan cover band (my second) and was having the time of my life. My success living in D.C. made me start thinking that before it’s too late, I should experience another country and another culture.

The idea of just picking up and going to another country seemed risky, romantic, and exciting.

A colleague who grew up in Portugal told me about her country, which, I had to admit, I knew almost nothing about. But she made it sound like heaven. So, in the fall of 2019, I made a solo trip to Porto, Portugal’s second-largest city near its northern border with Spain.

There aren’t many places I visit where I instantly think, “Hey, I could live here,” but Porto was one of them. I found it wholly accommodating. It was diverse, the people were friendly, the city and surrounding Douro Valley were beautiful, and the country was steeped in history. On my first day, only hours after I arrived, I was walking down a narrow, cobblestone alley and heard someone on a patio high above singing and playing a guitar. It was a Bob Dylan song. I knew I was home.

I walked all over the city, sometimes clocking over 10 miles in a single day on my phone pedometer. I sampled the wine and port (and if it ain’t from Porto, it ain’t port) and tried many local dishes, including sardines, octopus, sausage, and pork. For my last night in Porto, I splurged on a great meal at a relatively new restaurant called Elemento in the heart of downtown.

Once I returned home, I put my plans to move fully in motion. Part of the reason was financial. I had a small pension and some investments in index funds, but that was about it. I read somewhere that a single person could live comfortably in Portugal for around $2,000/month, including everything. That was less than my monthly Social Security check. In D.C., I was spending almost $3,000/month to rent a small one-bedroom apartment.

I had an acquaintance, an expat and former Boston Globe reporter, living in Portugal, and sent him an email. I told him that I was thinking about moving there, but I was skeptical that a person could live on just a few thousand dollars a month. He and his wife were renting a home in Ponte do Lima north of Porto near Braga, and he generously sent me his monthly budget, the full details. It was true. What they spend on food, rent, utilities, even going out to restaurants, added up to only around $2,500/month.

So, that was my situation. Staying in America and maintaining my current standard of living most likely meant working 40 hours a week until I “shuffled off this mortal coil,” as Shakespeare put it. In Portugal, I could work part-time or not at all, and with savings and my SS check, live maybe not like a king but perhaps like a prince. And, oh yeah, everyone has free health insurance, even expats. It’s guaranteed in the country’s constitution.

It all sounded too good to be true. But there was another, more complicated reason why I felt it was time to leave my native country. The intense polarization, the politicization of everything, was tearing the country apart, wearing me down. I kept hearing Rufus Wainwright’s song Going to a Town, in which he sings, “I’m so tired of America.” After working for years in Washington, D.C. politics, and decades before that in Maine, yes, I was tired of America — exhausted.

I scheduled a vacation for August 2021 and bought tickets months in advance. This time, I planned to visit Lisbon, the country’s capital and largest city, to explore the area and compare it to Porto. I decided I needed a contact in Lisbon, a local, someone who could show me around and tell me what life is really like in Portugal. I found a dating app and scanned for women in Lisbon. There were very few, and of the three that I sent a note to, only one answered. Her name was Vera. She lived about 20 minutes west of Lisbon in a town on the coast called Estoril.

I told her I was coming over in a few months and asked if she would sit down over a coffee just to chat about living in Lisbon. “I would be honored,” she answered. Over the next several weeks, we continued chatting, moving from the dating app to WhatsApp.

At first, we’d chat maybe once a week. Then it became several times a week, then daily, sometimes several times a day. I discovered that you can make free video calls on WhatsApp, even overseas, and soon, we started video calling regularly. We grew quite close — very close. We sometimes talked for hours.

Vera was charming, smart, funny, full of life, and laughed at all my dumb jokes. She soon sent pictures of herself and her neighborhood, including some of her on her local beach, looking quite tan and lovely. When I showed the pictures to friends, they were certain I was being catfished.

“No way,” one said. “She’s fake.”

“Has she asked for money yet,” another said. “She probably just wants a green card.”

Why would she want a green card? She had a good job and a family in Portugal, twin daughters in their 20s. She certainly wasn’t looking to leave. Besides, I’d seen her and talked to her on video calls. She was the real deal, and I was smitten.

Vera had a vacation coming up in August that didn’t correspond to my visit. She suggested I change my plans and come during the same week as her vacation. That way, we’d have plenty of time to tour the area together and learn all about what might become my new home.

She became my official tour guide, at least that’s how I described her in my Facebook posts about my trip, misleading all my friends. The truth was, she was much more than that. The moment I stepped off the plane after my seven-hour flight from D.C. and saw her in the flesh for the first time, it was like reuniting with a lost love, that’s how close we’d become.

I still remember (and think about) our first kiss at the airport. And the relationship only deepened over the next week. Timing is everything in this world, and by happenstance, coincidence, or divine intervention, we found ourselves at the same crossroads of our lives, ready for each other.

I rented an Airbnb in Estoril not far from her apartment. Vera showed me around her neighborhood, and we walked along the shore to Cascais, a vibrant coastal town of restaurants, shops, and hotels. I had my first taste of authentic Portuguese cuisine when I ordered fish at the Reverse Pool and Beach Lounge overlooking the harbor. They brought the whole fish to the table for inspection before cooking it. “Look at the eyes,” the waiter said. They were clear, plump, and shiny, not cloudy or dull, a sure sign that the fish was fresh. I approved.

Later in the week, we toured Lisbon, a teeming cosmopolitan metropolis full of history, old monuments, ancient architecture, religious symbols, and plenty of tourists. The first stop was A Brasilleira, one of Lisbon’s oldest and most historic cafes in the Chiado neighborhood. My friendly and trusty guide provided the historical context for many of the buildings and monuments as we walked through the great archway, the Terreiro do Paço, and onto the Praça do Comércio, a huge square (329,000 square feet) facing the Tagus River. 

The day ended with a sunset cruise in the harbor, with close-up views of the 25th of April Bridge, the big suspension bridge across the Tagus connecting Lisbon to Almada. Many people mistake this as a copy of the Golden Gate Bridge due to its similar color, but it was actually designed by the company that built the Oakland-San Francisco Bay Bridge, only it’s twice as big. Passing under it sounded like a huge hornet’s nest, with cars and trains buzzing across the metal grid. With the sun going down and a near-full moon rising on the other side of the bay, it was a dazzling end to a spectacular and very romantic day.

On my last full day in Portugal, I took my first baby step toward getting residency by applying for a NIF—the Portuguese Número de Identificação Fiscal. It’s basically a Social Security number, except it’s used in all transactions. You really can’t do anything without it. I got an email from the outfit I hired to handle my NIF application notifying me that it had been approved, and we headed to a bank to open an account. It took over an hour, but in the end, after I transferred money from my U.S. bank account to my new one, I was given a debit card for my account. I felt official, the first step to making Portugal my new home.

Up to this point, I didn’t think I’d move anytime soon, but Vera changed all that. For one thing, she discouraged me from settling in Lisbon. It would be more expensive than living just outside the city, and she worried that since she worked in Sintra until 6 p.m. every day, it was unlikely we’d see each other more often than on weekends if I lived in Lisbon.

We were a couple now. We both wanted to spend more time with each other and living in the same time zone became an immediate priority. So we agreed: I’d go home and start the lengthy process of obtaining my visa while she would look around for an apartment for me near her place. If we hustled, and with luck, I thought I could make the move by the end of the year.

It would be a sprint, but I wanted to be in Portugal, and I wanted to be with Vera. The race was on to get my ducks in a row to apply for a residency visa. Portugal offers a variety of visas depending on your circumstances, whether you’re a student, investor, digital nomad, or retiree (and the categories have changed since I applied). I applied for the D8 residency visa for digital nomads and people who want to freelance remotely.

The visa would allow me to stay in Portugal for four months, during which I would apply for my residency permit to stay for two years. I gathered my bank statements and tax filings, Social Security letters, employment contracts, passport photos, and fingerprints, and crafted a personal statement on living in Portugal. On top of that, I had to make an appointment with VFS Global, the outfit that the Portuguese Consulate uses to outsource its visa application process, for an in-person review and submission of my application.

I was told that it would take three weeks to two months or more to get my visa approved. But the most important thing I had to do was find a place to live. I needed to include a copy of a one-year lease agreement for an apartment in Portugal with my application, and that’s where Vera came in. She had a realtor friend in Estoril she enlisted to help, and before long, she was sending me listings of apartments to rent.

She even visited many of them and gave me her reviews. Finally, in early October, she sent me pictures on WhatsApp. “This apartment is amazing! Incredible! Perfect! The kitchen is enormous!” It was a two-bedroom, two-bathroom (with a bidet!) apartment on the third floor in Carcavelos, near shops, restaurants, the train station, and only a few minutes walk to the beautiful, huge beach (Praia de Carcavelos). The owner was asking €1,200/month.

Vera was right; it looked perfect. I’d already booked a flight to return to Portugal in late October to search for an apartment, but Vera was worried someone would likely scoop up this bargain before I came over to check it out. I trusted her judgment and told her to tell the realtor I would take it, sight unseen.

Against the realtor’s recommendation, I offered €900/month (they don’t usually haggle much in Portugal, it’s more of an American thing), and after a short negotiation, we agreed to a two-year lease for €1,000/month. The realtor emailed me a copy of the lease for my signature and the deal was done. I had a home in Portugal. It was really happening.

I had a storage unit in Maine that I’d stupidly been renting for years, so I made a trip to clean it out, separating personal goods and mementos from the other junk I hauled away or donated to Goodwill. I went to my brother’s house in Boston for Thanksgiving and left some things with him—a big TV, my prized 1971 Fender Telecaster, some books and personal items.

My daughter Heather joined us for Thanksgiving. Coincidentally, after living for years in San Francisco, 3,000 miles across the country from me, she had recently moved back to Boston just as I was moving across the Atlantic. Some things never change. Like me, she worked remotely, for her job with Reddit. I was so proud of her accomplishments and thought about all I’d miss so far away.

It was tough saying goodbye. But she was fine with it and encouraged me to go, even saying she was proud of me for making the move. And she was right: since moving to Portugal, I’ve spent more time with Heather than in all the years I spent in D.C. She’s visited several times. It’s only a 6-7 hour flight from the East Coast and I’ve found that family and friends are anxious to visit.

Next was my appointment with VFS Global, which I couldn’t arrange until December 8. I saw a lot of online chatter about the difficulties people were having with the cumbersome bureaucracy, but for me, everything went smoothly. I had all my documents in order and the woman who handled my application was friendly and cheerful.

After she reviewed and accepted everything, I asked her, “Do I really have to wait in the U.S. until my visa is approved?” “Well,” she said with a sly smile. “You’re supposed to.”

I took that as a green light to head over to Portugal as soon as possible, which was good because I’d already booked my flight for just a week later, Dec. 16. Then came the packing, which was no small task. Deciding what to take and what to leave behind wasn’t easy. Neither was muscling all my clothes and other belongings into three large suitcases, along with a carry-on bag, two guitars, and my desktop iMac. The sum total of my earthly belongings.

On the day of my departure, as I was cleaning the apartment and packing my last items, there was a knock on my door. My twin brother Doug surprised me with a farewell visit to see me off. He gave me a little device, about the size of an iPod, that translates English into Portuguese when you speak into it. I was touched. The whole notion that I was leaving home and traveling to a distant, unknown country with an uncertain future ahead of me was finally sinking in. I was taking a big leap, leaving my life behind and starting a new one overseas.

Due to some travel troubles, I got to Lisbon exhausted and a day late. But I’d made it. I was, unbelievably, in Portugal, in beautiful Carcavelos, in my new home, my big apartment, to start a new life, with a long story about how it all happened. In the many times I’ve retold it, I’ve realized it’s really a love story. It’s about how I fell in love with Portugal, with Vera, and with life itself. You really can begin again.

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Maine-born Dennis Bailey is a former journalist and communications expert who lives in Carcavelos. His new book is Ola Portugal, from which this article is excerpted.