Exploring Scotland, particularly the Highlands and islands, can be challenging without a car. When I was planning my route for travels north of Glasgow, I was *this close* to renting a car and pre-paying for it online. It was only because of a chance conversation with an Edinburgh cab driver — who was so enthusiastic about train travel — that I decided to head north by train instead. And, as it’s happened so many times before, I had a wonderful connection with a fellow passenger.

The 3-hour train ride from Glasgow to Oban is stunning. Sit on the left the Edinburgh cab driver had told me, so that’s what I did. As promised, the view was incredible. At about two hours into the ride, the train was less than a quarter full, and the best views had migrated to the other side, so I moved across the aisle to a four-seater section for the added leg room. Shortly after that, a man boarded my train car with dog — a beautiful black Lab. The man must’ve seen my expression (I don’t have a poker face!) and the fact that I was making googly eyes at his dog.

Him: Do you want him by you?

Me: Yes!

He sat across from me with the dog beneath the table between us. I patted him (the dog) while the stunning Scottish Highlands and Lochs whizzed by my window.


I’m a grateful veteran of spontaneous train conversations with strangers, and they always start slowly and simply. Someone makes the first move, and it goes from there. My new train neighbor asked me how long I was in Scotland, and I answered for a while and told him where I’d been in the country so far. He was a native Scotsman who’d been sailing for weeks in the Hebrides and was about to sail some more. He said that he loved visiting America and that New York and Hong Kong were his favorite big cities.

I mentioned my travels in Hong Kong and compared it to Japan. He said that Japan was his wife’s favorite place. I said that it was MY favorite place too.

Train conversations are the best.

When people ask me how long I’m traveling, I usually don’t say for a year. I know that what I’m doing is a huge privilege and that I’m very fortunate. But I was clearly talking to an adventurer so, when he asked how long I’d been traveling, I came clean and recited my elevator speech:

I did something a little crazy. I sold my house, got rid of most of my stuff, and now I’m traveling the world for a year.

He immediately responded by saying something he’d repeat later during our journey:

You’re doing the right thing.

We talked more about traveling and taking risks. I told him about the man who’d breakfasted beside me at an Irish B&B. A man who’d seemed bothered by my adventure and grilled me with questions: What’s your plan B? Are you that confident you’ll be able to find a job when you get back to your regular life?

I wanted to say to that man: No. Are you that confident you’ll wake up in the morning?

The Scottish man on the train, however, seemed to understand why an open-ended journey was less scary to me than continuing down a predictable path.

He shared a bit about himself too. I learned that he invested in technology and took pride in his boat and had sailed for decades. He told me about the island where he and his wife had gotten married and showed me a video of his dog playing in the sea. We talked about politics and the Brexit vote. He mentioned kids and grandkids. He also seemed pleased and proud to learn about my wonderful experiences in Wales and Scotland and about how kind the locals had been.

If I had to guess, I’d say that he was in his mid-60s and, while there was nothing pretentious about him, and he was dressed in rugged (what I will call) sea wear, I could tell that he ran in significantly higher social/income circles than I do … or ever will!

When our train terminated in Oban, he got off first and disappeared into the crowd. I stayed behind near the platform, preoccupied with my Google phone map, configuring the route to my Airbnb. After a few minutes, I looked up to see him walking toward me, hand extended for a farewell shake. We wished each other good luck then went our separate ways.

A few weeks ago, a friend texted me, asking if anything “fabulous” had happened.

How can I adequately explain that it’s the simple moments that are so magical to me? The ones that feel present, organic and real, and wouldn’t make the cut in a film script. I’ll never see my train neighbor again, or any of my other previous connections, but they’re the ones who make travel special, and I hope my memories of them last for a long time.

What also tickles me was the string of events that made my conversation with him — and so many other conversations with strangers — possible. A cab driver’s casual comments, switching sides on the train … a dog!

It underscored the thing I treasure so much about going solo. Had I rented a car, or traveled as a twosome, I never would’ve had that experience.

Two adventurers on a train, sharing a dog and a chat. I’m going to be smiling about that for quite a while.

That’s my idea of fabulous.