A Red Car, Seven Songs, and a Lesson I’ll Never Forget

Before my first trip to Cuba, I thought I knew exactly what to expect.
Most Americans do. Classic cars. Cigars. Colorful buildings. A destination frozen in time. And while all of those things certainly exist, they aren’t what captured my heart.

What captured my heart was the culture.

The moment I arrived in Havana, I felt it. Music seemed to spill from every doorway. Not just from clubs and restaurants, but from homes, street corners, open windows, and passing cars. Art wasn’t hidden away inside museums. It lived in the streets. On walls. In studios. In conversations. In the pride people took in sharing their stories. The city felt alive. Not polished. Not manufactured. Alive. 

One minute you’re admiring a piece of artwork created by a local artist. The next you’re watching someone dance salsa as if the music were simply part of everyday life. The classic cars were every bit as beautiful as I’d imagined. The cuisine was delicious. The seafood was fresh. The cocktails were flowing. And yes, the handsome Cuban men certainly didn’t hurt either. But what surprised me most wasn’t any of those things. It was the people.

The hospitality in Cuba is unlike anywhere I’ve experienced. Conversations don’t feel rushed. People take time. Taxi drivers become storytellers. Strangers become friends. The culture isn’t performed for visitors. It’s simply lived. And visitors are invited into it.

One of my favorite memories happened during that very first trip.

I had booked a photoshoot around Havana, and part of the experience included being escorted through the city in a beautiful red classic car. The driver took us from location to location while the photographer captured images throughout the city. 

As we cruised through Havana’s streets, old-school hip hop played through the speakers. At first, I loved it. Then I noticed something. We kept hearing the same songs. Over and over again. Finally, I asked him: “Why don’t you change the music?” He laughed and explained something I had never considered. Internet access was expensive. Downloading music was expensive. Storage space for downloaded music was expensive. The music he had was the music he treasured. It was such a simple conversation. But it gave me a glimpse into a reality very different from my own. 

As we continued talking, I mentioned that I actually knew some of the artists whose songs were playing. I showed him photos. His excitement was immediate. I’ll never forget the smile on his face. For the rest of the afternoon, we talked about music, culture, life, and the artists he admired. What started as a photoshoot became a genuine connection. By the time I returned home, I couldn’t stop thinking about that conversation.

The following year, before heading back to Cuba, I asked a DJ friend to create a thumb drive loaded with old-school hip hop and R&B. Hours and hours of music. Music I knew he would appreciate. Once I arrived in Havana, finding him became my mission. I searched. I asked around. I looked for that red classic car everywhere. Days passed. 

Then, just before I was scheduled to leave, I found him. And somehow, he remembered me. When I handed him the thumb drive, his face lit up. The excitement. The gratitude. The surprise. It was one of those moments that reminds you why travel matters. Not because of where you go. Because of who you meet. That experience changed the way I view Cuba. Actually, it changed the way I view travel.

Before that trip, Cuba was a destination. After that trip, it became personal. I’ve now visited Cuba four times. I’ve taken salsa lessons. I’ve explored its art scene. I’ve ridden in countless classic cars. I’ve spent afternoons on the beach enjoying fresh seafood and far too many cocktails. And every single visit has given me a new story.

But when people ask me why I love Cuba, I don’t tell them about the cars. I don’t tell them about the beaches. I don’t tell them about the nightlife. I tell them about the driver. Because that story represents everything I love about the country. The warmth. The humanity. The culture. The connection.

Cuba isn’t what most Americans think. It’s richer. Warmer. More welcoming. More vibrant. And far more personal. That’s why I keep going back. And that’s why I can’t wait to return again.