I don’t know if everyone has had this experience—but maybe you have. It sneaks up on you. You travel to a new place, and something clicks. It’s the architecture, the landscape, the people, the pace. My wife would probably say it’s an imprint on your soul from another life—a lasting mark from a place that once offered you refuge.
The First Visit
The first time my wife and I visited Portugal, it felt like home. Not just the casual, “I bet it’d be nice to live here,” kind of thought—but I can imagine living here.
We could picture ourselves walking the steep, narrow streets climbing away from the Douro River in Porto as we navigated our daily commute or errands. Grabbing coffee at a favorite corner café. Making friends with people who somehow feel like old friends the first time you meet them. Spending holidays hiking the volcanic islands of Madeira or the Azores.
Returning, Again and Again
As of 2025, we’ve been to Portugal four times over eight years. Porto and Lisbon—multiple visits exploring the steep, narrow streets and alleys. A week each on Madeira and the Azores—hiking and driving across the volcanic islands. South along the Atlantic coast and Northeast through the Douro River Valley from Porto—on the back of a Vespa. We’ve sampled the amazing food, amazing cultural locations and events, and, of course, the port and wine. Every trip just deepened that feeling of belonging.
Traveling with Family
In the summer of 2021, we brought our two daughters along. They felt it too—that strange connection.
Here’s one story that sums it up.
We landed in Lisbon after a long flight, only to face a three-hour customs line. COVID-era travel staffing had hit hard; only two officials were working. Every time a new one appeared, the crowd broke into applause—only to realize they were just swapping shifts. By the time we made it through and found an Uber, we were exhausted, hungry, and slightly delirious.
There was a pizza place across the street from our Airbnb—close, open, and with good reviews. Perfect.
Our younger daughter, nine at the time, came in buzzing with tired energy and started dancing (the memorized choreography kind that every kid learns and practices with their friends in elementary school halls and playgrounds). The wait staff seemed to recognize a family at the end of a very long travel day—they smiled and welcomed us warmly to a table by the front window, brought my wife and me a couple of beers, and then took our daughter outside and had her teach them her dance in the narrow Lisbon street. We were home.
It was day one of our two-week trip.
The Return Visit
Weeks later, after hopping between several cities in France and back through Porto for the São João festival (an unforgettable night—more on that in another post), we returned to Lisbon for a few final days. On our last evening, we decided to stop by that same pizzeria again.
The moment we walked in, the staff recognized us. They visibly lit up, hugged our daughter, laughed, and immediately took her back outside to dance again—family energy. It’s a big part of why we keep going back.
To me, that story captures exactly what we love about Portugal: the warmth of the people. We are also drawn to the cozy medieval streets, the ocean air, the river valleys, and those volcanic islands sitting proudly in the middle of the Atlantic. We can’t wait to go back.
More images from the trip:
