Cuba

Day 1: A city frozen in time

As soon as we arrived in Havana, we knew exactly what we had to do: tour the city in one of the beautifully preserved classic cars that are everywhere here. We hired a driver, climbed into a gleaming 1950s convertible, and off we went. Havana is a city of contradictions — ambitious government buildings next to crumbling houses, Soviet-era austerity alongside scrappy private enterprises, grand colonial architecture that’s simultaneously gorgeous and desperately in need of a fresh coat of paint. It’s colorful, cheerful, vibrant, and utterly charming in a way that only a city with this much character can be.

• Classic car tour: Classic Cars in Cuba
• Accommodation: Airbnb in Havana

Day 2: A history lesson on wheels

We spent the day walking downtown Havana — through narrow streets and alleys, past vibrant markets overflowing with fruit and conversation, into churches with peeling frescoes, and around plazas where live music seemed to spill out of every doorway. Che Guevara’s face is everywhere: tattoos, murals, posters, T-shirts, government buildings. The colors of this city are extraordinary — turquoise, coral, bright yellow, faded pink — every building a different shade, as if Havana decided long ago that neutral tones were for other countries.

But what fascinates us the most is the cars. Standing on a sidewalk watching traffic go by in Havana is like watching the country’s history roll past. Gleaming 1950s Chevrolets and Fords from the Batista era — some lovingly restored, others held together by ingenuity and prayer. Sturdy Soviet-era Ladas and Moskviches from the decades after Castro’s revolution, when the US imposed sanctions and the Soviet Union became Cuba’s lifeline. And a smattering of newer Peugeots and Renaults, mostly government-owned taxis, since import fees make private car ownership a luxury few can afford. The cars don’t begin to tell the full story of Cuba, but it’s fascinating to see so much history imprinted so visibly in the traffic.

Day 3: Christmas Eve dinner with our hosts

We spent another morning exploring Havana, but the real highlight came in the afternoon. Our Airbnb hosts, Mali and Hector, invited us to join their family and friends for Christmas Eve dinner — an invitation that caught us completely off guard and touched us deeply. We sat down to a holiday meal with the whole group, swapped stories late into the evening, and learned that Mali and Hector had actually helped develop internet-based lodging in Cuba and played a key role in bringing Airbnb to the country. Sitting at their table, eating home-cooked Cuban food on Christmas Eve with people we’d met two days earlier, was a reminder of why we love traveling this way — staying in people’s homes instead of hotels opens doors you didn’t even know were there.

Day 4: Viñales

Why is Cuba famous for cigars? That’s what we were wondering when we set out for Viñales, a small town set in a scenic valley in western Cuba, surrounded by rocky karst hills and cliffs. The valley is known for growing tobacco using traditional agricultural methods and for its hand-rolled cigars.

On our first day in Viñales, we headed to the tobacco fields, hoping to catch a farmer at work. It wasn’t long before we found what we were looking for: a farmer working in a field of young tobacco plants. As we shot photos of this charismatic man in the glow of the morning light, we asked him about the process that would turn his plants into cigars.

“All of my tobacco is grown organically, then harvested and dried in that drying house over there, for at least three months,” he explained to us. “The government buys 90% of the leaves for a very low price” — to be used in the government-owned factories that produce brand-name cigars. “And I get to keep 10%, for the hand-made cigars that I sell locally.”

The farmer stopped pulling weeds when his wife brought a cup of coffee over. As soon as he finished the coffee, he traded the empty cup for a cigarette. With a big smile he said, “In Cuba, three things keep us going: coffee, tobacco, and rum!”

The farmer’s wife showed us the drying house, where we learned that the dried tobacco leaves get fermented with the family recipe of honey, lime, rum, and other ingredients. The soft parts of the leaves are then separated from the stiff center, which contains most of the nicotine. “Our cigars aren’t as addictive as the factory ones,” she explained, “because we remove the middle part of the leaf.”

Back in town, we enjoyed listening to a group of friends playing Cuban music. We watched sunset over the lush green valley, then returned to our Airbnb, where our hosts (Norma and Carlos) served up a delicious home-cooked meal. Carlos makes the best mojitos!

• Drive from Havana to Viñales: Discover Viñales
• Accommodation: Airbnb in Viñales

Day 5: Cigar rolling

Our guide Oleg took us on a tour of the Viñales area today, and the highlight was visiting a farmer who walked us through the full cigar-making process: cutting, layering, rolling, and trimming, all by hand with practiced ease. Then he lit one for each of us to try. We’re not smokers by any means, but the fermented tobacco had a rich, sweet-and-smooth flavor that we have to admit was pretty wonderful. Experiencing the whole journey from the plant in the field to the finished cigar in our hands gave us a genuine appreciation for the craft.

We had a delicious lunch at an organic farm nearby, then spent the afternoon exploring more of the valley before settling in to watch yet another beautiful sunset from a new vantage point. The Viñales valley at the golden hour is so beautiful.

• Viñales tour: Discover Viñales

Day 6: To Trinidad

Most of today was spent on the road — riding in yet another classic car from Viñales to Trinidad, which is about the most Cuban way to travel imaginable. We stopped briefly in Cienfuegos for lunch but didn’t have time to explore, which gives us an excuse to come back. We arrived in Trinidad in the late afternoon, and immediately fell for the town’s cobblestone streets and colonial architecture. In the evening, we wandered on our own, soaking up the atmosphere.

Our hosts, Amaro and Yamira, are both doctors who left their hospital jobs to run a homestay — a telling detail about life in Cuba, where tourism can pay better than medicine. Their home is beautiful, their hospitality was warm, and the fact that two physicians chose this path says something important about the contradictions of the Cuban economy.

• Drive from Viñales to Trinidad: Taxi Viñales Cuba
• Accommodation: Hostal Dr Amaro y Dra Yamira

Day 7: On the artistic side

Our guide Adonis took us on a walking tour of Trinidad this morning — through Plaza Mayor, up the viewing tower for a panoramic look at the terracotta rooftops, and through the Museo de Historia Municipal, where the city’s Spanish colonial past comes to life. Trinidad feels like it’s been lovingly preserved in amber: cobblestone streets, pastel-colored buildings, and a pace of life that seems intentionally unhurried.

The afternoon was even better. An acquaintance had connected us with Yram, a local photographer and videographer, and we spent hours geeking out over his work, discussing equipment, and swapping ideas. What struck us most was how much Yram accomplishes with so little. When he needed a boom arm for smooth camera motion in his documentaries, he couldn’t buy one — so he built one from scratch using aluminum tubes, household hardware, and his own tools. We were amazed, and a bit ashamed of how much we spend on gadgets back home.

Yram showed us one of his documentaries about his friend Carlos César Román, a painter and sculptor who has exhibited all over Cuba and internationally. We were so impressed that we asked if we could meet him. Luckily, Carlos was available, and Yram took us to his studio.

The studio walls were covered with sculptures of Fidel Castro — all made entirely from found materials. We’d heard that Castro banned public exhibitions of his image unless authorized by the government, which made the work feel even more daring. “Fidel told us to never throw anything away, that everything can be fixed or reused,” Carlos told us with a grin. “I think he would approve.”

Each piece had a story. In one, Fidel’s beard is assembled from empty pill packages: “When people are feeling bad in Cuba, they often turn to Fidel, as if he’s the medication that will fix their headaches.” Some of his work is more overtly critical. One piece features a giant mousetrap attached to a door painted with the Cuban flag, the key to the lock dangling right next to the trap. “If you grab it, you might get caught,” Carlos explained. “To me, that sums up what Cuba is all about.”

Carlos’s work is creative, beautiful, and daring. He and Yram embody something we saw again and again in Cuba: through ingenuity, people can achieve remarkable things with very little. It’s the kind of afternoon you can’t plan — and the kind that stays with you long after you leave.

• Tour: Trinidad Sightseeing

Day 8: New Year’s Eve with new hosts

We said goodbye to Trinidad and got a ride to Santa Clara, where we met our new Airbnb hosts, Antoine and Saily. We connected with them immediately. Their home is decorated with a creative, tasteful eye — every corner has something interesting to look at — and Antoine turned out to be a spectacular fashion photographer. We spent a good part of the evening admiring his portfolio and talking about the challenges and rewards of doing creative work in Cuba. It’s a recurring theme on this trip: the people we stay with are just as memorable as the places we visit.

To top it off, Antoine and Saily invited us to ring in the New Year with them and their friends. Great food, great conversation, and the kind of easy, happy atmosphere that made us forget we’d only known these people for a few hours. A perfect way to welcome the new year in Cuba.

• Drive from Trinidad to Santa Clara: Taxi Viñales Cuba
• Accommodation: Airbnb in Santa Clara

Day 9: Looking back at the revolution

Saily connected us with her friend Emilio, who took us on a walking tour of Santa Clara — and turned out to be a great guide. Funny, passionate, and a natural storyteller, he brought the city’s history to life. The 1958 battle of Santa Clara was the pivotal moment in the Cuban revolution, with Che Guevara emerging as a national hero, and the city wears that history proudly. We visited Che’s mausoleum, the iconic statue of Che holding a child, and the Tren Blindado monument — an actual armored train that Che’s forces derailed and captured in one of the revolution’s boldest victories. Standing next to it, with Emilio narrating the chaos of that day, history felt very close.

Tomorrow we fly back to Havana and then home. Cuba has been extraordinary — not for its beaches or resorts (we skipped those entirely), but for its people. Every host, guide, and stranger we met had stories to tell and warmth to share. We came curious and we’re leaving inspired. It’s the end of a great trip, and the start of a new year.