We Missed the Train and Found Everything

In Callejón de Hamel in Havana, I thought I lost my lens cap. Any other day, any other version of me, that would have been a full stop moment. Instead, I kept dancing. And somewhere between the drumbeats and the crowd and the color of everything that Sunday morning, I found it. Right where I had been standing all along.

That, it turns out, is a metaphor for everything I have learned about travel lately.

I moonlight as a travel advisor, which should tell you everything about how seriously I take a good itinerary. Schedules, reservations, contingency plans for the contingency plans. I am good at it, and I love it. But somewhere along the way, I started leaving room. A morning with nothing on it. A neighborhood with no agenda. A train I was not entirely sure about. And what happened in that space surprised me.

In Granada, a wrong turn led us down a narrow street and straight into a flamenco show we never would have found on any list. We stayed. We made friends. We left with a story we still tell. In Barcelona, we were there for Pride but missed a turn to the bar and stumbled into her stall instead. Confetti, joy, and a stranger who became a friend. One we still make a point to see whenever we are back in Barcelona. That was over 15 years ago. In Budapest, we missed a train. A fellow traveler, a conversation, and a reminder so clean and simple: people are kind. They really are.

And then there was Charles de Gaulle. A last-minute hotel booking, a bar, razor clams, and a conversation that led to, and we cannot make this up, someone in Keanu Reeves' orbit. Some detours are better than others.

These were not accidents. Or rather, they were — and that was exactly the point.

The Albaicin, Granada

Callejon de Hamel, Havana

Keleti Station, Budapest

There is a kind of travel that goes perfectly according to plan and comes home with beautiful photographs and checked boxes. And there is another kind that goes sideways in the best possible way and comes home with something harder to name. I have started chasing the second kind. Last-minute bookings, loose itineraries, mornings left open like an invitation. It has been fabulous and wildly entertaining and more memorable than almost anything I carefully arranged.

This is not me telling you to throw away your plans. A good plan is a gift, especially for first-timers, families, or anyone working with limited time. But inside that plan? Leave a gap or two. Take the wrong turn if something catches your eye. Miss the bus on purpose. Say yes to the thing that was not on the list.

Summer is coming. Everyone is planning. Plan well, then plan a little less. The best things I have ever experienced on the road were never on the itinerary. They rarely are.