Cuba
Where Time Slows Down and Cigars Tell Stories
TL;DR — For the Impatient Traveller
Cuba was a childhood dream shaped by stories of Fidel Castro, Che Guevara, and Ernest Hemingway, vintage American cars, and the mystique of Cuban cigars. In 2018, while visiting the United States for work, I finally decided to chase that dream with a motorbike road trip across the island. Starting in Havana, I rode through the countryside to Viñales, stayed with a local Cuban family, visited tobacco farms where cigars are still rolled by hand, and experienced a rhythm of life that felt frozen in time. The journey later took me briefly to Varadero’s Caribbean beaches before returning to Havana’s music-filled nights. In the end, I even lost most of the handmade cigars I had been gifted during a humorous interrogation at Miami airport. But the trip proved something deeper — the real value of travel isn’t what you bring back, but the conversations, landscapes, and moments that stay with you long after the journey ends.
The Lost Mumbaikar says:
“Cuba is proof that history doesn’t always move forward. Sometimes it parks itself and waits.”
The Oppotunity
In 2018, work took me to the United States, I decided to chase that childhood dream.
The plan was simple:
Spend a few days in Miami, then fly east to Havana and explore Cuba on a motorbike road trip. Cuba — A Childhood Dream Rolled in Tobacco Leaves
Cuba had lived in my imagination long before I ever saw it on a map.
Growing up in the 1980s, I would often hear names like Fidel Castro, Che Guevara, and Ernest Hemingway in the news while my father listened to the radio. At that time, I didn’t understand politics, but those names carried a strange mystery.
At the same time, another image fascinated me —
old vintage American cars, hand-rolled cigars, and cocktails born in Havana bars.
Somehow, the idea of Cuba stayed quietly in my mind for decades.
I always imagined one day standing in a tobacco field, holding a freshly rolled cigar, and seeing how that entire culture was built. Getting some fresh cigars from Cuba and smoking them from my terrace in JLT apartment-something I could only dream about then, long before I bought my place in Cayan Tower was the ultimate dream.
That dream stayed with me, which is there in the ending of this blog.
Exploring Cuban before Cuba
In 2018, work took me to the United States, and I decided to chase that childhood dream.
I spent a few days in Miami before flying east to Havana, planning to explore Cuba on a motorbike road trip.
During my stay in South Beach, I visited I Love 305 on Ocean Drive, Miami Beach. The place is a Cuban-inspired restaurant, bar, and nightlife spot created by Pitbull to celebrate Miami culture and the famous “305” area code. Pitbull, who is of Cuban origin and grew up in Miami, has been associated with several bars and nightlife venues in the city. As a fan of his music, it felt like a fitting place to start a journey toward Cuba.
While I was there, I spoke with one of the staff members who was Cuban. When I told him about my plan to travel through Cuba, he shared a few funny stories about Pitbull’s early struggles, his rise to success, and the charity work he does for Cuban communities. Before I left, he gave me one piece of advice -when I reach Havana, I should visit El Floridita, famous for its cocktails and its long association with Ernest Hemingway.
It felt like the perfect introduction to the Cuban journey that was about to begin.
Arrival in Havana
The moment I landed at José Martí International Airport, the contrast was immediate.
I had just come from Dubai and Miami, cities of glass towers and endless technology. Havana was the complete opposite.
The airport felt simple.
Almost frozen in time.
Outside the terminal stood old American cars from the 1950s and 1970s, painted in bright colors and rumbling slowly along the road.
People were relaxed.
Unhurried.
No one seemed to be chasing anything.
But my plan was to chase everything.
As always, I had planned a packed itinerary-a continuous road trip on a motorbike, nights filled with music and Cuban cocktails, local food, staying with local people, beaches, caves, and of course the cigar farms that had fascinated me since childhood.
My original plan included five destinations:
- Havana
- Viñales Valley
- Cienfuegos
- Trinidad
- Varadero
My Havana Plan
I had booked a small hotel in the city centre because my motorbike rental was arranged nearby.
For the first two days, I decided to explore Havana itself.
And Havana deserves time.
The city feels like a living museum of another era. One of the main reasons is the long US trade embargo imposed after the 1959 Cuban Revolution led by Fidel Castro. Because imports of cars, machinery, and many modern products were restricted for decades, the country continued using what it already had. That is why you still see American cars from the 1950s, old Soviet vehicles, and buildings that look frozen in time. Instead of being replaced, many of these machines and structures were simply repaired again and again.
Driving along the famous Malecón, Havana’s oceanfront boulevard in a vintage car is almost a ritual for every traveler. The ocean crashes against the wall while pastel-colored buildings line the horizon.
Havana carries layers of history everywhere.
Revolution stories.
Spanish colonial architecture.
Music drifting from open windows.
Hemingway’s Havana
One place I had always wanted to see was the bar where Ernest Hemingway used to drink.
At El Floridita, the famous Daiquiri cocktail became legendary. The bar proudly calls itself “La Cuna del Daiquiri” – the birthplace of the Daiquiri. Hemingway was such a regular visitor that a life-size bronze statue of him now sits at the same corner of the bar where he used to stand and drink. Bartenders still talk about how he preferred his Daiquiris stronger and less sweet than usual.
Hemingway loved Cuba so much that he eventually settled there in the 1930s. He spent nearly two decades living near Havana, writing some of his most famous works while enjoying the island’s fishing culture, music, and relaxed lifestyle.
His home, Finca Vigía, located just outside Havana, is now a museum where visitors can still see his books, writing desk, typewriter, and even his fishing boat Pilar. Many of the rooms remain exactly as he left them, with thousands of books and personal items still in place. Several parts of his famous novel The Old Man and the Sea were inspired by the fishermen he met in Cuban villages.
Standing there, you begin to understand why he chose Cuba over the United States. The island offered him something rare -quiet mornings, deep-sea fishing, strong rum, and a culture that valued storytelling and conversation. Life moved slower, and that rhythm suited a writer.
Another famous bar closely connected to Hemingway is La Bodeguita del Medio, known for its Mojito cocktail. A famous line often attributed to him is written on the wall there:
“My Mojito in La Bodeguita, my Daiquiri in El Floridita.”
Whether or not he actually said it, the sentence has become part of Havana’s folklore.
And that is what Havana does to people.
It has a strange rhythm that slowly pulls you in.
The Motorbike Road Trip Begins
On the third day, my real adventure began.
My ride was a Piaggio three-wheel motorbike, with two wheels in the front for better grip. Cuban roads are not always smooth, and the extra stability helped.
Leaving Havana behind, I started riding west toward Viñales.
The roads were narrow two-way highways passing through farms and small villages. Sometimes the scenery reminded me of Kerala villages -green fields, children playing near the road, and farmers working quietly in the distance.
The pace of life felt beautifully slow.
Along the way I saw children walking home after school, chatting and laughing with their friends. There were no school buses waiting to pick them up, just groups of kids walking together with excitement and dreams in their eyes. Watching them reminded me of my own childhood days in Morak, when phones did not exist to steal attention and every walk home was filled with stories, jokes, and small adventures.
It felt strangely familiar.
I stopped at a few beautiful places along the way. One of them was the Cueva del Indio, a famous cave near Viñales where a small underground river flows through the limestone hills. The surrounding area was incredibly green, with dramatic mogote hills rising from the tobacco fields.
Nearby I also visited Palmarito Waterfall (Salto de Palmarito), a quiet natural spot hidden in the countryside where the sound of flowing water and birds made the entire valley feel peaceful.
At one of the small roadside tourist spots, I tried a local Cuban pork dish cooked slowly over charcoal. The meat was incredibly fresh, “no preservatives, no frozen ingredients”, just simple seasoning, garlic, lime, and salt. It was served with rice, beans, and plantains, and it tasted far better than many expensive restaurant meals.
Sometimes the best meals on a road trip are the simplest ones.
Viñales Town and it’s magic
When I reached Viñales, I finally understood why this place is so famous.
The valley is surrounded by giant limestone hills called mogotes, rising dramatically from the tobacco fields. These formations create a landscape that looks almost unreal — green valleys, red soil farms, and massive rock walls emerging from the ground.
Instead of staying in hotels, I stayed with a local Cuban family in a traditional home.
This was not Airbnb.
This was not a hotel.
When I asked a shopkeeper where I could stay, he simply pointed me to a local house.
That decision changed the entire experience.
In the evenings, the valley becomes incredibly peaceful. Farmers return from the fields, horses walk slowly along the roads, and the sunset lights up the mogote hills.
Viñales doesn’t feel like a tourist destination.
It feels like time slows down there.
Life Inside a Cuban Home
The landlord and his wife welcomed me warmly. My original plan was to stay only one night, as I had another aggressive itinerary waiting. But slowly I began to slow down and decided to stay two days instead.
My stay included both food and accommodation. It was an elderly couple, and I think their income mostly came from this Cuban version of Airbnb, where they provide a room and home-cooked meals prepared with genuine care.
They cooked simple but delicious Cuban food, and I spent most of the time in the kitchen watching the entire process as the meal was prepared. Later we sat together and ate while talking late into the night.
They spoke Spanish.
I spoke English.
Yet somehow we understood each other.
We spoke about family, children, and life. I showed them pictures of my wife and kids, and they made me promise that one day I would come back with them.
The atmosphere reminded me of a peaceful village in Kerala.
Roosters crowing in the morning.
Quiet streets.
No noise of traffic.
No rush.
In that moment, I realized something powerful.
Wealth is not always measured in currency.
Sometimes wealth is the peace you feel when life slows down.
Away from notifications.
Away from noise.
Just people, food, and laughter.
Extending my stay by one more day was completely worth it. Cuba felt like a place I could return to many times. Even today, whenever I smoke a cigar, I tell Sunitha that one day we will go back to Cuba together because I have told her so many stories about this place and the cigars that came from its fields.
Visiting the Tobacco Fields
The highlight of Viñales was visiting a tobacco farm.
Here I finally saw how Cuban cigars are made.
The process is fascinating. The tobacco leaves are first harvested and then hung inside drying barns for several weeks. After curing, skilled workers roll the cigars by hand using techniques that have been passed down through generations.
Many of these farms supply tobacco leaves to some of the largest cigar brands in Cuba.
The farm owner and supervisor spent nearly two to three hours with me, patiently explaining every step of the process. They shared local drinks while showing how the leaves are selected, dried, and rolled.
When they learned that I had come all the way from Dubai just to see this, they were genuinely delighted.
Before I left, they surprised me with a bundle of 30–40 handmade cigars as a gift.
It was a gesture I will never forget.
The only regret I had was that I didn’t have local Cuban currency with me to give them as a tip. They had spent so much time explaining everything, offering drinks, and sharing their craft. But in those days, there were very few ATMs in Cuba, and I didn’t see a single one in Viñales.
Even without a tip, they simply smiled and wished me a safe journey. Another reminder of the warmth and generosity of the Cuban countryside.
Cancelling My Original Plan
My itinerary originally included Cienfuegos and Trinidad.
But Viñales changed my mindset.
Watching people enjoy simple things -laughing together, eating $1 churros, old men smoking cigars while gossiping in the street. It made me pause.
There were very few smartphones.
Very few ATMs.
Most cars were from the 1950s.
Yet people seemed surprisingly happy.
I began to wonder if modern life brings more anxiety than happiness.
Instead of rushing through my plan, I cancelled the next destinations.
I decided to visit only one more place.
Varadero.
From Viñales to Varadero
After extending my stay in Viñales Valley, I finally continued the journey toward the coast.
I started early in the morning around 6 AM, knowing that I had to return to Havana by evening.
The ride from Viñales to Varadero is roughly 300 km, and on a motorbike it takes most of the day. As the road moves east, the landscape slowly changes. The quiet tobacco countryside begins to fade and the road starts approaching the Caribbean coast.
Varadero is famous for a reason.
The moment I reached the beach, the contrast was striking.
Crystal-clear turquoise water.
Endless white sand.
The sea looked almost unreal.
But I didn’t swim.
I had only come to see the Caribbean from Cuba’s side, not to spend the day there. Varadero felt very different from the places I had just experienced. Unlike the authentic rhythm of Havana and the peaceful countryside of Viñales, Varadero is more commercial and resort-driven, built mainly for international tourists.
After spending time immersed in the local Cuban culture, I didn’t feel like staying long in a place designed mostly for vacation packages.
Still, I walked along the beach for a while, absorbing the view of that vast Caribbean horizon.
Before leaving, I stopped at a small seaside restaurant where fishermen had just brought in their catch. I tried a simple but delicious local grilled fish — fresh snapper seasoned with lime, garlic, and sea salt, served with rice and black beans.
Simple food.
Fresh from the sea.
After that short stop, I got back on the motorbike and began the ride back toward Havana, carrying with me one more contrast that makes Cuba fascinating — a country where untouched countryside and international beach tourism exist just a few hundred kilometers apart.
Simple food. Perfect taste.
And Back to Havana’s Nights
By evening I rode back toward Havana. Instead of rushing through tourist spots, I simply slowed down and enjoyed the rhythm of the city.
At evening, I found myself returning to the Malecón, the famous oceanfront boulevard where locals gather to talk, drink, sing, and watch the waves crash against the wall. Sitting there at sunset, with vintage cars rolling past and music drifting through the air, it felt like a scene from another era.
Next day, I wandered through Old Havana, exploring lively squares like Plaza Vieja and Plaza de la Catedral, where street musicians play late into the night.
Havana’s nightlife has its own charm. It isn’t flashy like Miami or Dubai. Instead, it is full of small bars with live salsa music, people dancing freely, and conversations stretching long into the night.
The city has also become a popular film location. Parts of The Fate of the Furious were shot on Havana’s streets, using the colorful classic cars and colonial architecture as the perfect backdrop. Another famous film, The Godfather Part II, recreated pre-revolution Havana scenes inspired by the city’s history.
Walking those streets at night, it was easy to see why filmmakers love Havana.
The city already feels like a movie set. No cameras required.
The Miami Interrogation
Returning to Miami brought an unexpected experience.
US immigration officers questioned me for quite some time.
Technically, Americans cannot travel to Cuba purely for tourism.
There are 12 authorized travel categories, including religious travel, educational activities, and cultural exchange etc.
When asked why I went, I mentioned religious travel and named Havana Cathedral.
The officer looked at me and laughed.
“A whole week in church?”
He clearly knew I was there for travel.
Then came the next question.
“Anything to declare?”
I confidently said no.
Then he pointed at my bag.
“You sure about that?”
Inside were dozens of Cuban cigars.
The officer reminded me that I had said I went for religious reasons.
For a moment, I thought I would lose everything.
After some negotiation, I asked if I could at least keep two cigars as a memory.
He laughed again and surprisingly agreed.
The rest were confiscated.
The Irony of Cuban Cigars
Before leaving Dubai, many friends had asked me to bring Cuban cigars. You can buy cigars in Dubai, but the freshly hand-rolled ones from the farms in Viñales were something special.
Those cigars were probably worth quite a bit, and enjoying them later on my terrace, something I had dreamed about for years, it never actually happened.
But strangely, losing them never bothered me. Because the real value of that trip wasn’t the cigars.
It was the conversations.
The landscapes.
The slow rhythm of Cuban life.
And the reminder that sometimes the richest experiences come from the simplest places.
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