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Scouting Trip Lessons: When the City You Research Isn’t the City You Choose

We spent months planning a scouting trip to Lisbon, confident it was the right city for our family. But after battling Covid and experiencing the realities of city life with toddlers, we discovered that Lisbon felt overwhelming for this stage of life. Exploring surrounding towns gave us a surprising sense of ease and reminded us why being flexible on a scouting trip is so important.

Brett
September 12, 2025
5 min
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Before the Trip: Why Lisbon Looked Perfect on Paper

Before our scouting trip, I spent months researching Portugal. Every article, blog post, and Youtube video seemed to confirm what I was already leaning toward: Lisbon checked all the boxes. It had high-quality schools and healthcare, a major international airport, rich cultural experiences, and a diverse, urban environment full of opportunity for our family’s future.

When we finally booked our trip, I felt confident. Lisbon was going to be it and we would spend our entire month exploring different Lisbon neighborhoods.

A Rough Start: Getting Sick Abroad During Our Scouting Trip

But life had other plans. Within 24 hours of arriving, we all came down with Covid and lost nearly 10 days to quarantine and recovery. Once we emerged, tired but determined, we had just over two weeks left to make the most of our scouting trip. We narrowed our list of neighborhoods and got to work.

Discovering the Challenges of Lisbon with Kids

After a few days exploring central Lisbon, we noticed something surprising. We felt overwhelmed.

We’re used to city life. We live in central Phoenix, one of the largest cities in the U.S., but we also live in a house with a yard and plenty of space. The transition to apartment living, navigating steep hills, and relying on public transportation while carrying two toddlers felt like a lot all at once.

Exploring Beyond Lisbon: Cascais, Setúbal, and the Silver Coast

That’s when some of those casual park conversations started to pay off. We met families who lived outside of the city and invited us to visit their hometowns. We spent time in places like Cascais, Setúbal, and smaller towns along the Silver Coast.

Once we got out of the city center, everything shifted for us. The pace was slower. The sidewalks were flatter. Our kids had more room to play, and we felt a greater sense of ease. It didn’t mean Lisbon had nothing to offer. It just meant that for this stage of life, while our kids are tiny, we needed a softer landing.

Why Staying Open Matters on a Scouting Trip

It reminded me how important it is to stay open during a scouting trip. Even with months of research, you don’t really know what’s going to feel right until you’re there in person. That’s exactly why Scoutly Plans is built to guide you through different cities and neighborhoods, not just one destination. You might be surprised by what resonates.

Final Reflections: Finding the Right Fit Abroad

For us, that place wasn’t where we expected. And that’s the beauty of actually showing up and seeing it for yourself.