Living in Portugal: A Once-in-a-Lifetime Cruise that Changed Our Lives

Sometimes life really does feel like a dream. It just requires taking it one step at a time and a whole lot of checklists. Our Mediterranean cruise was a major catalyst for so many things. Looking back I can see how it shaped where we are today, living in Portugal.

We bought, what we thought, was our dream home in North Portland in Fall 2012 and quickly began to offer space available to guests on a short-term basis. But, in planning for the trip of a lifetime in Fall 2013, we quickly realized there were no property management companies serving the Portland metro area. No one was offering a service to help homeowners manage their short-term rental listings while they were away.

Ensourced Origins

Like we always do, we persevered and made it work. We pieced things together finding month-long renters for our upstairs suite to love on our elderly cat and take care of the trash and shared kitchen.

We found help from kind and generous friends to clean and prepare our rental spaces for short-term guests. Then, we managed guest communications between glasses of delicious wine, awe-inspiring artwork at Roman museums, and striking Greek architecture.

When we returned we thought to ourselves, that was fun! Maybe we can roll this business idea out on a broader scale. We talked to a lot of people to get their perspectives and decided we could create a win-win-win. We could be financially successful in helping other hosts find their freedom while also making guests happy.

In 2013 we began by cleaning other Airbnbs in the area and developed a system for success. In 2014, we took on our first property management client from a friend who needed help managing her lovely, SE Portland four-square home.

After a few months managing her property, we realized we could roll this out on a larger scale, and busted our butts for the next several years doing just that. We grew to a crew of 9 of the best souls out there, taking care of, at one point, close to 30 management properties and 50 cleaning-only units.

Time Keeps on Slipping

The amount of detail orientation and constant concentration it took to manage that business was all-consuming. It seems like the years just flew by in the blink of an eye. We were tethered to the business and took it with us wherever we went. We answered guest emails and seemingly urgent phone calls in the middle of important family events and reliably responded to booking inquiries late into the evening and first thing in the morning.

Then, there was the time we had to drive back home at speeds that would make Mario Andretti nervous when a guest ever-so-thoughtfully over-torqued a pipe under our sink while we were trying for an overnight getaway. Their “fix” to a seemingly low-water pressure issue in the bathroom sink caused a huge flood that poured out over our beautifully maintained hardwood floors. Water streamed down the historic lathe and plaster walls, soaking the basement apartment below, saturating air ducts, and basically wreaking chaos along the way and causing a big, soggy mess.

Waking in a Nightmare

We blinked, we sighed, and when we opened our eyes, it was Spring 2020. We started hearing about this unique type of virus that would soon take the world by storm. In what felt like a nightmare, the cancellations poured in, much like the flood we’d previously experienced. Guest after guest after guest canceled their reservations. They were, understandably, afraid to travel, terrified to contract this deadly disease for which there was no vaccination and no cure.

Our stomachs dropped. There went our revenue, along with that of our hosts, for the foreseeable future and there was no end in sight. Already experiencing thin margins, we didn’t have a lot of room to be without earnings for that long. We did everything we could to pivot like we always do. Specifically, we made most rentals available for month-long tenants to appeal to traveling nurses and digital nomads taking advantage of new corporate flexibility but these measures only went so far.

Heads Above Water

I’m not going to lie, the first few months were insanely difficult. We experienced fear for ourselves, fear for our families, fear for our friends, and fear for our business. It was a terrifying time. We scrambled to keep ourselves healthy and financially stable, driving food delivery for long hours daily to make ends meet.

By the way, here’s a big THANK YOU to everyone who tips their drivers well. I’ll never forget the kind, generous lady who tipped us $20 for her dinner and literally made our night. I almost cried. Her tip meant that it was one whole hour we could go home early and rest. We could spend time with our poor dog. We could have one extra hour to avoid the constant go-go-go of the meal delivery game.

Then, like anything else, the new and scary sort of becomes normal and pedantic. We found ways to cope and learned to live with elevated anxiety. But, in those dark, deserted streets, we also started to realize some things about ourselves and what we wanted for our future.

One of our largest observations was that the way the United States dealt with the coronavirus was probably the way it would handle the impending climate crisis. With hope. Maybe a supportive clap, a solemn prayer, and a whole lot of pretending like it wasn’t happening.

Heads in the Sand

We knew we couldn’t bury our heads in the sand and expect to remain healthy. We wanted to live in a society that truly cared for each other, whether weak, elderly, medically vulnerable, or immunocompromised. Each and every one of us deserves the best opportunity to live a full life. No one is expendable.

We considered whether we should stay and continue to fight for the rights that would uplift everyone, like universal healthcare. Or, perhaps it was time to shift our perspective and find ease in a society that already embraced this framework.

So, we began to explore alternatives. While we searched for a country accepting Americans during the health crisis, we discovered that Portugal offered a pathway to residency and even citizenship down the road.

We watched a lot of YouTube to hear from other Americans who’d made the leap and decided we could make a go of it in the new, old world by living in Portugal.

Shifting Focus

We made a plan to emigrate and started making checklists. With much heartbreak and a lot of tears, we sold our beautiful, 1927 craftsman home.

We took an intermediary step with an apartment in Vancouver, WA. This cozy spot allowed us to experience a smaller space and make it a home. We continued to shed belongings that we couldn’t commit to bringing thousands of miles across a continent and an ocean.

Our days were filled with managing existing clients while finding a buyer for the property management piece of our business and accomplishing the many tasks to prepare for our move. Nights were filled with creating even more checklists, debating with ourselves about the plans we were making, and challenging our assumptions to make sure we were on the right track.

Living in Portugal

We met with our immigration consultants on January 20, 2021 – just two weeks after the Insurrection at the Capitol Building. The consultant said they’d been flooded with Americans seeking their help. We explained it was merely a coincidence, that we’d been working toward living in Portugal for quite a while by then.

Nonetheless, they were eager to help and gathered information about our circumstances. Then, they helped us prepare for the immigration appointment with the Portuguese authorities that took place just before Memorial Day. Remarkably, our D7 visas were approved about a month later, just before July 4th! We sold our beloved life-saver that hauls everything, Vivianne, shipped two pallets of can’t-live-withouts, and were on our way to living in Portugal by September 2021!