My Portugal, My People, My First OWR Trip

There are trips you take, and then there are trips that take you. Portugal was the latter. It wasn’t just another country stamped into a passport. It was something more, something that will sit in me in ways I’m yet to digest. 

Portugal has always been one of those places I wanted to visit. But every time I tried to plan it, something would happen, and so plans changed, life pulled me in a different direction, and I’d end up somewhere else instead. After a while, I half-joked to myself that maybe I just wasn’t meant to see Portugal.

And yet… here I am, after finally experiencing it with OWR. And now I know I was absolutely meant to see it this way, with this group, on this trip, in this moment.

But here’s the tricky part: I thought that because this was not only my first Portugal trip but also my first ever OWR trip, I’d sit down and instantly write the best blog I’ve ever written. The one that perfectly captured it all. Except, what exactly is “the best blog”?

Is it the one that paints Portugal in the most vivid colors? The one that’s clever and smooth and instantly makes you want to book a flight? Or is it the one that’s honest enough to admit that sometimes words fall short, that experiences are too layered, too human, too alive to be squeezed neatly into paragraphs?

If it’s that last one, then maybe this is my best blog. Not because the writing is flawless, but because it’s real, chaotic, and full of impressions I’m still processing. 

“BEYOND ITS PHYSICAL BEAUTY, PORTUGAL TOUCHED ME SOMEWHERE DEEP. IT REMINDED ME THAT TRAVEL CHANGES WITH US”

Beyond its physical beauty, Portugal touched me somewhere deep. It reminded me that travel changes with us. In my 20s, I sometimes chased countries, counted passport stamps, checked boxes. This time, I realized I wasn’t collecting places or stamps. I was collecting people. And when I look at Portugal on a map now, I don’t just see cities and coastlines. 

I see faces, energy, connections. I see the group of strangers who became my Portugal.

There’s a Portuguese word — saudade — that has no perfect English translation. It’s a longing, a nostalgia, a sweet ache for something you know can’t be replicated but will always stay with you. 

That’s exactly how I feel about this trip.

Because while landscapes shape the story, it’s the people who give it meaning.

“AND JUST LIKE THE CITIES, EACH PERSON I TRAVELED WITH LEFT THEIR OWN MARK ON ME”

Portugal often sparks a debate — Porto or Lisbon? As if one could exist without the other. But that’s the secret someone told me: you don’t have to choose. You let each city speak in its own language. Porto, soulful and grounded, whispers with the weight of history. Lisbon, colorful and sprawling, sings with a rhythm only those patient enough can hear. Both are beautiful, but neither exists to be compared.

Each sings its own song. Like people, they’re not meant to be compared. They’re meant to be experienced.

And just like the cities, each person I traveled with left their own mark on me. Here’s what they gifted me along the way:

Jamie

My roommate, who showed me what conscious roomateship looks like. There’s a special kind of comfort in being able to co-live with someone you just met, and Jamie made it effortless. Who knew that doorless bathrooms in boutique hotels could be such an icebreaker? We learned quickly that trust, respect, and a little humor can turn strangers into a safe space.

Ali

Organized yet spontaneous, funny yet firm, soft yet serious: Ali carries these qualities in the best way. I learned something new from her every day. From seeing how she prepared pastel de nata in a cooking class in Porto, to following her lead into quirky shops in Lisbon, and hearing about her friend baking cookies back in the States (the most beautiful I’ve ever seen btw!) she added meaning to every moment of the trip. She was also my partner in crime for wine and pastel de nata liquor shots.

Fernanda 

Our local tour leader, who didn’t just show me Portugal, but made me fall in love with it. Fernanda carried the country in her heart and passed pieces of it to us each day in the way she described a palace, in the food she recommended, in the pride she carried for her culture. She was more than a guide; she was Portugal personified.

Jannine

With her unapologetically bougie approach, Jannine reminded me that balance is the secret to good travel: knowing when to lean into group time and when to retreat into one’s own space. She showed me that it’s not indulgence, but wisdom, to know what you need in each moment.

Becca

Becca reminded me that you can do things entirely on your own terms and still fit into a group. She found her rhythm, honored her independence, and still blended with the rest of us. Watching her was like watching someone write their own rhythm while still being part of the band.

Richard

Richard reminded me that even on vacation, our minds don’t need to completely switch off and it’s okay to carry real life with you. Through stories about his kids, he grounded us in the bigger picture of what matters. He also happened to be part of my wine crew, which meant his wisdom was always paired with laughter and good company.

Shar

Humility wrapped in quiet power: that was Shar. With her sense of style and her soft, deliberate voice, she taught me that strength doesn’t always roar; sometimes it’s woven into subtlety, into posture, into choice. 

Joanna

Joanna taught me how to accept generosity with grace. She gave me more compliments in one week than I’ve had in years, enough that I had to write a few down. Instead of deflecting, I learned to receive. To let kindness land. To simply say thank you.

Mike

Mike was pure talkative energy, the spark that kept the group buzzing. Loud, joyful, unapologetically himself. He showed me the beauty of turning the volume up, and filling a space with laughter. His presence was a reminder of how much joy can come from simply leaning into who you are, without seeking approval.

Steve

And finally, there’s Steve, the person without whom this experience wouldn’t have been mine to live. He’s also the one who taught me that not everything needs comparison. Lisbon doesn’t have to beat Porto, and travel doesn’t need to be measured. With him, I was reminded that sometimes the best gift is just to be. To exist without analysis, expectations, and comparisons. And in his presence, I could simply be myself too, more than I thought possible. 

“A FEW WEEKS AGO, WE WERE STRANGERS. NOW, I CAN’T IMAGINE PORTUGAL WITHOUT THEM”

When I look back on Portugal, I see the pastel palaces, the vineyards, the ocean cliffs but what I feel is the people. A few weeks ago, we were strangers. Now, I can’t imagine Portugal without them.

This trip was never really about the checklist moments. The pastel de nata mattered because someone thought of me and got it for me, and that little gesture made the moment feel full of care and connection. The tuk-tuk ride mattered because we were clinging to each other, laughing so hard strangers couldn’t help but smile.

The wine in the Douro Valley mattered because it came with talks that felt like they’d been waiting for that exact table. And that catamaran in Lagos? It wasn’t just about the ocean views. It was about passing sunscreen like contraband, dancing barefoot on deck, and realizing we weren’t just floating on water but in a space where everything felt lighter.

“SOMEWHERE OUT THERE, MY NEXT OWR STORY IS ALREADY WAITING TO BE WRITTEN (DON’T KNOW WHEN AND DON’T KNOW WHERE); ALL I KNOW IS I CAN’T WAIT TO SEE WHO’S IN THE NEXT CHAPTER”

Travel has a funny way of proving that you can learn as much from someone you’ve known for a week as from people you’ve known your whole life. And that’s the true gift of a trip like this: not just the country, but the community you build along the way.

Portugal will always stay with me, but so will Jamie, Ali, Becca, Fernanda, Janine, Joanna, Shar, Richard, Mike, and Steve.

And I wouldn’t trade either for anything.

Somewhere out there, my next OWR story is already waiting to be written (don’t know WHEN and don’t know WHERE); all I know is I can’t wait to see who’s in the next chapter.