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 how it had on my previous visit. Tourism had been shut down hard, and you could sense the strain everywhere — fewer visitors, more desperation, and a general edge that hadn’t been there before.

It started simply enough. I ran into a hotel employee on the street who helped me track down cigars that were difficult to find at the time, post-COVID. He was friendly, helpful, and easy to talk to, and I was able to track down some 'real' Cuban cigars. 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. Food and drinks were wildly overpriced for what we’d ordered, and suddenly it felt less like a casual lunch and more like something I’d been walked into. Then another guy showed up — sketchy, aggressive, started pushing a currency exchange I hadn’t asked for, and clearly didn’t want. I said no. He didn’t let it go.  I politely paid the bill and left.

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. I didn’t wait around. I flagged a cab and went somewhere else. Nothing bad happened — because I listened to my gut when something felt off.

That night in Havana was a reminder that real experiences aren’t always comfortable, and awareness matters as much as curiosity. Most people are good. I still believe that. But when you’re travelling alone, especially in places hit hard when tourism disappears, small signals matter — prices that don’t add up, pressure you didn’t agree to, people who appear out of nowhere.

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.