Cuba

There’s a certain thrill in surrendering control — in letting fate decide your next step. That’s the premise behind Travel by Dart, and this time, the dart landed on Cuba.

To many, Cuba is vintage cars, colonial facades, cigars, and salsa music. But I wasn’t looking for postcards. I was looking for pulse. For paradox. For people. And Cuba — complex, alive, defiant — gave me all of it and then some.

This is the real Cuba — not the one behind the souvenir counter, but the one behind the curtain.

Havana: Classic Cars and a City That Refuses to Quit

Landing in Havana felt like stepping onto an old movie set...if that movie were directed by history and written by resilience. The streets are filled with classic American cars from the 1950s, each one a chrome-plated act of defiance against time and embargo.

I jumped into a cherry-red convertible and cruised through Havana’s iconic Malecón, with the sea on one side and crumbling colonial facades on the other. Touristy? Sure. But it’s the kind of touristy that still slaps you with beauty.

But the heart of Havana isn’t in the drive — it’s in the stories. I met mechanics who keep these relics alive without access to parts, using kitchen tools and motorcycle engines to Frankenstein them into shape. Innovation here isn’t an option. It’s survival.

Hemingway’s Havana: La Bodeguita del Medio

Tourist trap or sacred ground? La Bodeguita del Medio somehow manages to be both. Ernest Hemingway’s favorite bar still pours mojitos like water, but you come for more than the drink. You come to feel his presence. To lean on the same bar he did. To leave your name scrawled on the wall beside a thousand others, forming a chaotic mural of wanderlust and memory.

I wasn’t just sipping rum. I was time traveling with a literary ghost.

Viñales: Where Cuban Cigars Are Culture

When you leave Havana and head west into Viñales, the landscape shifts — and so does the energy. Limestone cliffs rise dramatically from emerald fields. But it’s not just the views that matter. It’s the rhythm of life.

Here, I visited a tobacco farm where cigars are more than exports — they’re culture. The farmer walked me through the drying barns, where leaves hang like sleeping bats. He showed me how to roll a cigar with fingers that carry the wisdom of generations. We talked about soil, sweat, and superstition.

Then came the moment: lighting up my first freshly rolled Cuban cigar. Yes, I smoked. Slowly. Respectfully. And when the smoke curled upward, it felt like I was exhaling not just tobacco, but centuries of history.

Trinidad: A Town Frozen in Time

Next stop: Trinidad, a UNESCO World Heritage site where cobblestones tell stories and salsa seems to rise from the pavement.

The town is frozen in time — and yet alive in every sense. Colorful homes with iron grilles, rhythm echoing from open windows, roosters crowing like it’s still 1850.

I wandered with no map, getting lost in alleys that eventually led to local musicians, street artists, and an old woman selling pastelitos who insisted I take three for luck. (I didn’t argue. She was right.)

An Afro-Cuban Santería Ceremony in Santiago de Cuba

But the most surreal moment of the trip happened when I was invited to witness an Afro-Cuban Santería ceremony.

Inside a modest home in Santiago de Cuba, I sat across from a priest who didn’t speak English — but who somehow read my past, present, and future by throwing cowrie shells on the floor. The ceremony was intimate and spiritual. I was told things I had never shared publicly. I don’t know if it was magic, intuition, or something in between. But I left rattled — and deeply moved.

They offered gifts to Chango, the Orisha of fire, music, and thunder. In a world of influencer filters and shallow experiences, this moment cut deep. It was raw. Sacred. Real.

Santiago de Cuba and the Conga de los Hoyos

Santiago de Cuba is not Havana’s little brother. It’s its rebel cousin.

This is where Fidel Castro’s revolution found its voice. It’s where African roots are not just acknowledged — they are celebrated with force. And it’s where I found myself dancing in the streets with the Conga de los Hoyos, a Grammy-nominated band whose rhythms seem genetically wired into the city’s DNA.

It wasn’t a show. It wasn’t staged. It was Cuba at its loudest, boldest, and most unapologetically alive.

Faith on the Hill: Basilica del Cobre

High in the hills stands the Basilica de Nuestra Señora del Cobre, a place of pilgrimage and miracles. People come here with photos of loved ones, with letters, with crutches they no longer need.

I’m not Catholic, but faith is universal when you’re surrounded by so much hope. I watched people cry, light candles, and whisper prayers to a statue cloaked in gold. I didn’t need to understand every word to feel the emotion.

Cienfuegos: Cuba’s Whispered Secret

Before wrapping the journey, I made a quick stop in Cienfuegos — a coastal city where French influence dances with Caribbean soul. It’s cleaner, quieter, and somehow feels like a whispered secret compared to the other places I’d visited.

From architecture to attitude, Cienfuegos was elegance — the velvet lining of Cuba’s emotional rollercoaster.

Fidel, Che, and the Weight of the Revolution

Of course, you can’t come to Cuba and ignore the Revolution. I visited Fidel Castro’s grave — a giant stone with a simple engraving: “FIDEL.” No statues. No fanfare. Just a rock, as if to say: he was of the land.

In Santa Clara, I stood in front of Che Guevara’s mausoleum, trying to make sense of the iconography, the mythology, and the man.

Whether you revere or reject them, these men defined Cuba’s modern identity. To stand where they once stood is to confront history not just through books, but through energy.

What Cuba Really Feels Like

All of this — the ceremonies, the cigars, the color, the contradictions — is captured in my Travel by Dart Cuba episodes, which now air on Amazon Prime and on major international airlines like Emirates, American Airlines, and Virgin.

But no video, no platform, can fully contain what Cuba feels like when you breathe it in.

This article is just another attempt to do what the camera can’t: tell the stories behind the footage, the emotion behind the edits.

Cuba is not just a destination. It’s a mirror. It reflects resilience. It confronts comfort. It challenges assumptions.

It’s where nothing works — and yet everything moves. Where food might be scarce but music is endless. Where pain lives close to joy, and politics are always personal.

So yes — come for the cigars and cars, but stay for the conversations. Get lost. Be uncomfortable. Ask questions. Eat with your hands. Dance with strangers. Let yourself be changed.

Because behind the tourist curtain is where the real Cuba lives.

Watch the full Cuba series

Cuba was so rich it became a three-part Travel by Dart series. Beyond the episode above, watch This Is the Real Cuba — Beyond Tourism and How Cuban Cigars Are Made.

More Caribbean adventures

If Cuba’s mix of island soul and history pulls you in, the dart has landed on other Caribbean stories too — the painted streets of Curaçao, the twin islands of Antigua & Barbuda, the reefs of the Cayman Islands, and the rhythm of Puerto Rico.