A Night in Havana That Taught Me to Pay Attention

I don’t scare easily when I travel, but one night in Havana made me slow down and pay attention.

This was just after travel reopened post-COVID, and Havana felt different from my previous visit. There were fewer visitors, and I sensed a strain that I had not noticed before. That was my impression on this particular trip.

It started simply enough. I ran into a hotel employee on the street who helped me find Cuban cigars that were difficult to track down at the time. He was friendly and easy to talk to. As a thank-you, I offered to buy him lunch. He suggested a small café run by a friend and invited a couple of others along.

That’s where things shifted.

When the bill came, the prices made no sense to me. Food and drinks were far more expensive than I expected for what we had ordered. Then another man arrived and began pushing a currency exchange I had neither asked for nor wanted. I said no, but he kept insisting. I paid the bill.

Nothing dramatic happened, but the tone had changed. Enough that I finished up and left.

Later that night, I decided to check out a photography tip that had been mentioned during lunch—an event I was told would be happening. There was no event. But standing nearby was one of the same guys from the café earlier, watching. That coincidence was all I needed.

I didn’t confront anyone or wait around. I flagged a cab and went somewhere else. Nothing bad happened, and I was glad I had acted when the situation felt wrong.

That night reminded me that awareness matters as much as curiosity. Most people are good; I still believe that. But when I’m travelling alone, I pay attention to pressure I have not agreed to and situations that stop feeling comfortable. It is a different side of travel from the openness I describe in Saying Yes in Beijing. Both experiences have stayed with me.

Curiosity opens doors. Instinct tells you when it’s time to close them. And despite moments like this, Cuba remains an incredibly compelling place to photograph—if you’re curious to see what drew me there in the first place, you can explore the images in my Cuba Wall Art Collection.