Cuba, Three Times

A time capsule from 2017–2019, when the door was briefly open.

We ended up in the lounge of the Meliá Cohiba one night — a hotel on the Malecón in Vedado, named for the cigar, which felt like a sign — and a man named Dolan sat down near us and said hello.

He was late twenties, maybe thirty. Cuban, but lived part of the time in Los Angeles. Within a few minutes he had a Cohiba in his hands and was showing us things we didn't know we didn't know — the cut, the cedar, the circle of fire. The kind of lesson that changes how you smoke for good.

We tell that story in full over in The Ritual →. What matters here is that an unexpected night put us exactly where we needed to be. That's Cuba.

A Note Before You Read This

We went to Cuba three times — 2017, 2018, 2019. We went on support for the Cuban people visas, which is the category that opened up under Obama and meant you could travel as long as you were engaging with Cuban culture, Cuban people, Cuban everything. We were. Absolutely.

The warmth we remember from those trips has a specific shape. It was the warmth of a door opening after a very long time. Cubans are generous, genuinely curious, and extraordinarily hospitable — the kind of people who make you feel like a guest rather than a tourist. That never changed across three visits.

What changed was the weight in the background. Each year we went back, things felt a little harder. Less tourism. A visible strain. We're not going to make this political — but we saw it, and we'd be dishonest if we didn't say so.

This is a time capsule. We can't promise any of these places are still open. We can't promise the roads are the same or the currency works the same way or that Dolan is sitting in that lounge right now. What we can tell you is what Cuba felt like when it felt like possibility. And that if the door opens again, you should walk through it.

Where We Stayed

We stayed in casas particulares every time. Private homes, licensed to host guests — cheaper than hotels, warmer than hotels, more honest than hotels. On the first two trips we stayed with Clary at Villa Cary in Nautico, in the Playa district west of central Havana. Clary is the kind of host who makes you feel like you've done the right thing by showing up. The neighborhood is residential in a way that tourist Havana isn't — you're eating where people eat, walking where people walk.

The third trip we stayed in Vedado, and Vedado is where the city shows you a different face. The Malecón a short walk away. The Meliá Cohiba. The Hotel Habana Libre with its massive lobby and its layered history. Our rooftop Airbnb had a sea view and a host who answered every question we had.

Trinidad was also a casa. Fidelito, who runs the house, also drives. He picked us up in Santa Clara — we flew in through SNU on that last trip deliberately, to see the island from a different angle — and drove us through countryside that got greener and more dramatic with every kilometer. Fidelito talked the whole way. We didn't catch all of it. We caught enough.

Pinar del Rio: Go Every Time

You have to understand what Pinar del Rio is if you care about cigars at all. It's the westernmost province of Cuba, and the Vuelta Abajo region within it produces what most serious smokers consider the finest tobacco in the world. The soil, the humidity, the way the mountains shape the microclimate — you can feel it when you're there. Lush is almost insufficient as a word. It is aggressively, almost impossibly green. A must if cigars mean anything to you. Budget for the unexpected and you'll get there and back just fine.

Our 2018 guide was a man named Yobel — pronounced Joe-zel, don't forget — who knew those roads the way you know your own neighborhood. He took us to Luis Hectar Farm and introduced us to Osvaldo, who walked us through tobacco plants the way a painter walks you through a canvas. Where the leaves go. Why this one and not that one. What makes a wrapper, what makes a filler, what gets thrown away. You learn things in a field that no cigar shop can teach you.

We also made it to the Prito farm — met Prito himself, ate a meal there that we still talk about. On the farm or close enough not to matter. We don't have the name of the place. We don't need it. Some meals you carry in your body, not your notes.

The Cigars

The cigar that started everything wasn't a Cohiba. It wasn't a Montecristo. It was a Guantanamera.

Beige the Aficionado had been smoking non-flavored cigars long before Cuba entered the picture. I was still in the flavored world — the sweet, the smooth, the approachable. And then, on our first trip in 2017, we were at La Casa del Habano at the Hotel Habana Libre in Vedado, and someone handed me a Guantanamera, and I smoked it.

It was the first cigar that tasted like tobacco rather than vanilla or cherry or whatever smoothness had been added to make it easy. And it was — actually good. Complex in a quiet way. Not a big cigar, but an honest one. I call it my first big boy cigar. The discovery that changed what I reach for. Everything that came after started in that room.

The Monsdale came on that same first trip, at Club Habana on Fifth Avenue in Miramar. Club Habana is a social club in the old Havana sense — pool, restaurant, cigar lounge, the particular ease of a place that has been the same for a long time. The Monsdales aren't on display. You ask for them by name. Ask for Jorge. They're kept in a humidor in the back, house-rolled, the kind of cigar that doesn't exist outside the place it was made. We asked. We got them. They remain, to this day, one of the finest cigars we've ever smoked.

Most places we went, smoking outside with a drink or a meal wasn't an issue. Cuba is one of the few places where the cigar belongs to the moment — order what you want, light what you have, stay as long as you like.

Trinidad, Cienfuegos & the South Coast

In 2019 we went to Trinidad for the first time. We'd heard about the south coast beaches — the Caribbean side, calmer water, a different shade of blue than the north — and we wanted to see them. Playa Ancón delivered everything the rumor promised. White sand, warm water, the particular quiet of a beach that hasn't been built over. We stayed in the water longer than we should have.

The town itself is what happens when a colonial city gets preserved so completely it starts to feel like a film set, except the people living in it make it real. Cobblestone streets, pastel houses, music coming from somewhere you haven't found yet. That night we ended up at Casa de la Música — up the wide stone steps near the main church, at the top of the hill, where a band was playing and people were dancing under the open sky with the rooftops of the city spread out below. We had drinks. We smoked. Someone near us was dancing who clearly had no intention of stopping. It was one of those nights that asks nothing of you except to be there.

From Trinidad we made a day trip to Cienfuegos — about an hour west along the coast, and a completely different Cuba. Founded by French settlers in the early 1800s, the city has a European elegance that catches you off guard after the warmth and color of Trinidad. Wide boulevards, neoclassical architecture, a bay that seems to hold the light differently. We walked the streets, found WiFi in the square, and stopped at La Casa del Habano — a space so full of architectural detail it felt like stepping back in time. A beautiful, unhurried change of pace. Worth every kilometer.

The Nights

One of the best nights was the simplest — the rooftop bar at the Kempinski Havana in Vedado. Panoramic views of the city, warm air, a cigar going. Nothing more complicated than that. Some nights in Havana don't need a plan.

We spent another evening at the Buena Vista Social Night in Old Havana — a basement venue that carries the tradition forward in a space that feels like the 1950s kept in amber. Intimate, underground, the musicians extraordinary. We had drinks and let the music do what it wanted to do.

Somewhere in those evenings — we think it was the second trip, at La Casa del Habano at the Habana Libre — a musician played Guantanamera. The song, not the cigar. Live, in the room, the way it was meant to be heard. We had cigars going. We ordered another round. The version of Cuba you imagine before you go, and the version you find when you're there, are usually different things. But sometimes, in a moment like that, they line up exactly.

What We'd Tell You Before You Go

If It Opens Again

Cuba's rules for American travelers change — check current requirements before you book, as working with an approved travel agency may be required. And go with open eyes. The Cuba we experienced across three trips was worth every mile. What you find today may be different.

Cigar Matrimony traveled to Cuba in April 2017, June 2018, and September 2019 on support for the Cuban people visas. All experiences reflect conditions at the time of each visit. Cuba changes. Go with open hands.