The People Who Made My Trip: Why Bespoke Travel is About Human Connection

From an Aussie stranger-turned-friend in Italy to a Costa Rican surfer who now crashes on our couch, these are the people who made my trips unforgettable.

When I think back on my favorite travel experiences, it’s never just the scenery or the activities that come to mind. It’s the people.

Sure, I’ve seen beautiful beaches and stayed in stunning villas—but the moments I treasure most involve the people I never planned to meet: the stranger I shared wine with in Italy, the surf instructor who became family, the driver in Bali who still checks in via WhatsApp.

That’s the magic of bespoke travel. It isn’t built around rigid schedules or cookie-cutter itineraries. It leaves room for conversations, for real connections, and for unexpected friendships that linger long after your passport is put away.

These are just a few of the people who turned my trips into stories I’ll never stop telling.

When I think back on my favorite travel experiences, it’s never just the scenery or the activities that come to mind. It’s the people.

Sure, I’ve seen beautiful beaches and stayed in stunning villas—but the moments I treasure most involve the people I never planned to meet: the stranger I shared wine with in Italy, the surf instructor who became family, the driver in Bali who still checks in via WhatsApp.

That’s the magic of bespoke travel. It isn’t built around rigid schedules or cookie-cutter itineraries. It leaves room for conversations, for real connections, and for unexpected friendships that linger long after your passport is put away.

These are just a few of the people who turned my trips into stories I’ll never stop telling.

Ruby- a stranger in Italy turned friend

I met Ruby in Florence, on a hot July night, at a restaurant serving pasta out of a cheese wheel. She’s from Australia, bold in the best way, and had that kind of energy that made everything feel like an adventure.

What started as a quick chat about pasta turned into skipping down the cobblestone streets and getting drinks at a nightclub. While Ruby and I only spent one day together before I was off to my next destination, we still keep in touch via social media.

There’s no world in which I would’ve met her on a structured group tour. But bespoke travel gave me the space and freedom to follow a spark of connection, and I ended up with a friend for life.

Jobbie – The Surf Shop Owner Who Became Family

Our story with Jobbie started long before I was old enough to surf. He met my dad in the early 2000s, when my dad took his first trip to Costa Rica as a twenty-something just looking for waves. Jobbie ran a tiny surf shop back then—just a few boards, a hammock out front and a deep knowledge of the tides. They hit it off instantly. What started as a local helping a tourist turned into a decades-long friendship.

Years later, when we returned as a family, Jobbie was still there—same surf shop, same smile, just a little more sun-worn. He helped me stand up on a board, laughed when I wiped out, and somehow always knew where the best smoothie shops were.

But Jobbie wasn’t just our surf guide. He became part of our family. He’s helped us meet locals, took us to hidden waterholes and even made the trip to the U.S. to visit us—more than once. Now, every time we go to Costa Rica, seeing Jobbie is as essential as packing sunscreen.

It’s wild to think that a spontaneous surf rental two decades ago could lead to this kind of connection. But that’s exactly the point: bespoke travel leaves room for relationships to grow, not just memories to fade.

Made – The Heart of Bali in a WhatsApp Message

Then there’s Made (pronounced Mah-day), our driver during a trip to Bali—though calling him just a driver doesn’t really do him justice. From the moment he picked us up at the airport, he had this calm, steady presence that made us feel instantly taken care of. He knew the roads like the back of his hand, but also knew where to stop for the best roadside fruit, which temples were worth lingering at, and how to keep everyone laughing, even after long days in the sun.

What stood out most about Made wasn’t just his knowledge of Bali—it was how much he genuinely wanted to share it. He taught us phrases in Bahasa, made sure we never got overcharged at restaurants and showed us all of the local spots.

We only spent a week together, but years later, he still messages us on WhatsApp. Sometimes it’s a photo update of his family, sometimes just a friendly “how are you?” It always makes me smile—and reminds me that the connections we make when we travel don’t have to end when the trip does.

With Made, we didn’t just get from point A to point B. We got a window into Balinese life, and a small but meaningful friendship that’s lasted far beyond that trip.

Conclusion

When people talk about bespoke travel, they often focus on the luxury—private excursions, curated itineraries, beautiful stays. But to me, the real luxury is human connection. It’s meeting someone who opens a door you didn’t even know was there. It’s being welcomed like a local, not just treated like a guest. It’s friendships that last longer than your plane ticket.

Ruby, Jobbie and Made weren’t part of any pre-designed itinerary. I met them because bespoke travel gave me the time, space and openness to truly engage with the people around me. These moments didn’t just enhance the trips—they became the trips.

So when I look back, I don’t just remember the places. I remember the people who shaped them.

And honestly? That’s what keeps me traveling this way.