Planning is essential to travel, but the moments that really matter often happen when they’re least expected.

One of my favorite travel experiences happened when I was lost in the Welsh countryside. My travel companions and I were trying to get from Tintern Abbey to St. Briavels hostel, but strayed from the trail somewhere along the Wye River and ended up wandering around a small village in England.

As we stood around looking at our maps, a woman approached and asked if we were lost. Before long, Claire offered us a ride and we were cruising through the English countryside in her car. It was a brief encounter, but one that taught me about the hospitality of rural England and how people tend to help other people.

It was also something I never could have planned.

As I reflect back on my best travel experiences, many of them were similar; they happened during well-planned trip trips when I had the best of intentions, but were themselves moments of serendipity.

The recording below captures another such moment, albeit a smaller and more fleeting one. It was taken awhile back when I was rushing through Salt Lake International. As I walked by, a saw a man sitting on a bench playing harmonica. So I stopped to listen.

Airports are usually pretty frenzied places, and the harmonica struck me as a poignant counterpoint to the chaos. And significantly, it wasn’t part of my plan for the day. There’s no way it could have been.

We here at Tripping Over the World have written before about the value of getting lost. We’ve written about the value of serendipity. But the underlying idea behind all of these arguments is that planning can only take a traveler so far. In the end, the moment the plans fall away is often when the magic begins.

In Europe you can (and should) walk almost anywhere

Listen to a string quartet play in Roman ruins in the alps

How to meet people while traveling: Hitchhike, or pick up someone who needs a ride

— Jim Dalrymple II


Written by Jim Dalrymple II

Urbanism and travel writer. Also a journalist covering the news.


  1. I agree 100%, my friends and I ended up camping at a remote lakeside in Slovakia because we decided to throw caution to the wind and lose ourselves. It still remains one of the best experiences of my life!

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