When I lived in Germany as a teen, I spent a lot of time exploring the local towns. One of my favorite things to do was to start at a known location and then wander, intentionally trying to get lost before finding my way back. I found some of my favorite places this way, including hidden meadows in the English Gardens or one of my favorite markets. I wouldn’t have discovered them otherwise.
As an adult, pre-kids, I adjusted this approach to more of a structured flexibility – I’d have some destinations in mind but would open myself up to new discoveries along the way. In Rome, I found one of my all-time favorite restaurants by getting lost down an alleyway. Driving across France and stopping at random turnoffs, like the Caves aux Moines, taught me more about the country than I’d have gotten by sticking to the guidebook route.
But when I had kids, this approach felt daunting. I was nervous about the uncertainty of not having every move mapped out. What if a kid needed a bathroom when we were in the middle of a desert or had a meltdown in a boutique restaurant? And speaking of food, how would they react to local menus with foods they’d never tried (or heard of)?
Trialing flexible travel in the Azores
When my older son was 7, we decided to test out a return to a more flexible approach to travel. So we booked a rental car and a few hotels, left our 3-year-old with family, and headed to the Azores.
We had a general list of things we wanted to see, but very little outside of our hotels was actually booked. We navigated the island via rental car (an adventure in and of itself), taking things as they came and adapting as needed.
The weather didn’t always cooperate, like when our hike to view Sete Cidades was fogged in, though we managed to squeeze in a redo at the end of our trip and were rewarded for our efforts. And while food was a challenge for my son, he was open to trying everything and didn’t starve (yes to Portuguese muffins, no to hamburger with egg).
But we had a great, and most importantly, memorable time. We were also blown away by how open-minded our kid was and how he rose to and overcame every challenge.
There were moments where he whined and complained, but we also saw him push himself and accept that it’s ok when things don’t go as planned. With each hurdle, we saw his confidence grow.
One standout example was on a canyoning tour. The only kid in the group, he pushed himself to keep up on the grueling hike and jumped off all the waterfalls, showing up several of the adults.
What’s next?
Our trip to the Azores showed me that it’s possible to travel how I want and in ways that are meaningful to me, and that they can be meaningful to my kids, too. Everything wasn’t perfect or scripted, but my son rolled with it, and we made many new memories.
So, this year, we’re embracing our flexible approach to travel with both kids, aged 4 and 9. I’ll be documenting what works, what doesn’t, and what moments matter most to them.
Wish me luck!
– Megan
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