Moving Abroad with Kids: The Stroller Saga from Our Scouting Trip

Planning For The Trip

Every blog I read before our scouting trip to Portugal said the same thing: Don’t bring a stroller to Lisbon. “Too hilly,” they warned. “Too many cobblestones. It’s more hassle than it’s worth.”

But I packed our favorite Phil & Ted’s double stroller anyway.

As a mom of two toddlers recovering from Covid, I figured we’d need all the help we could get walking around the city of seven hills. On our first day out, Brett and I were gasping for air walking uphill in Graça and trying to maneuver a stroller through uneven sidewalks and narrow alleyways. I hated to admit it, but the bloggers were right.

That night, things went from inconvenient to… well, unforgettable.

Stroller Trouble

Someone broke into the first floor of our Airbnb building and stole our stroller from the lobby.

Yep, our beloved (and expensive) double stroller, gone.

It kicked off a whole unexpected chapter of our scouting trip abroad with toddlers: reporting a break-in to our host (who also had items stolen from the supply storage for his wine bar), navigating conversations about local building security, finding the neighborhood police station, and trying to file a theft report in Portuguese. It was our first real encounter with Portuguese bureaucracy, and it came with a lot of hand gestures, patient smiles, and of course paperwork.

Bureaucracy

Eventually, we filed a report with the police and Airbnb, and we were reimbursed for the loss. But even more importantly, we learned how to solve problems in a new system, in a new country, while caring for our family.

And surprisingly, a scouting trip without the stroller… worked.

We used baby carriers (often both girls wanted to be carried by dada at the same time) and planned slower outings. When we visited other cities like Cascais, Setubal, and Caldas da Rainha, we did see lots of local families with strollers. Flatter areas, wide sidewalks, and walkable parks made strollers way more manageable outside central Lisbon.

Final Thoughts

So here’s what I tell families now: if you’re planning a scouting trip with young kids, skip the stroller for Lisbon. It’s not worth the weight or the stress. Pack a great carrier, give yourself grace, and know that even when things go sideways, you’re still learning what daily life could look like in your future home. This is what scouting trips are all about, finding solutions to the unexpected so you can determine the best fit for your future life.

And if someone steals your stroller? At least you’ll have a great story to tell.