Just Back From…Cuba

When Tegan and Tyler Maxey told me they were starting a travel agency and running trips to Cuba, I was instantly intrigued. They are two of the most interesting people I know: the sisters grew up in The Bahamas, and after graduation Tegan worked as a deckhand on yachts and traveled the world, while Ty headed to Argentina for university. Tegan went on to co-found The Canvas, a sustainable retail platform, before selling her half of the company in 2021. Tyler moved back to Eleuthera to run visitor programs at the Island School, an environmental non-profit their parents founded, which is where we became friends. I quickly realized they are the kind of people who push you to be a more curious, compassionate version of yourself, and who could pull some strings to get you out of any mess you find yourself in. All that to say, they are exactly the people I wanted to travel to Cuba with for my first trip. 

We arrived in Havana late at night and Gaby, the co-founder of their company, Wanderers Club, met us at the airport. Gaby’s family left Cuba during the revolution and she grew up in the US, but decided to return to Havana a few years ago. She is their boots-on-the-ground contact there, always meeting people and keeping a pulse on what’s happening in the city and beyond. Gaby brought us pizza and beers, got us settled into the house and said she’d be back in the morning to exchange cash for us and walk us to our lunch reservation.

Our base for the week was a three-story home in Old Havana, the historic heart of the city that looks like the Havana you’ve probably seen in pictures—spacious sun-drenched plazas, tree-lined promenades, and old-school cars parked in front of beautifully crumbling, pastel facades. Even though it was a densely populated area, it felt like a small town—kids played kickball in the street, people left their front doors wide open, and old men dragged chairs onto the sidewalk to play dominoes at all hours. The house we rented was one of those quirky Airbnbs that has far too many chairs and hits somewhere between modern and dated (my bedroom decor was a mini fridge and the wooden base of an inoperable Singer sewing machine), but it was very clean, comfortable and convenient. The people who ran the Airbnb were lovely and I would definitely stay here again if I was traveling with a group. 

Our days were packed with activities, but when our schedule allowed, we had leisurely breakfasts in the dining room and sipped coffee on the large balcony. On our first day we oriented ourselves with a walking tour of the Old City and a sunset tour in candy-colored convertibles from the ‘60s, which is when we met one of our guides for the week, Amalia. She had grown up a few hours outside of Havana, and to hear both the historical context for what we were seeing/eating/doing and her lived experience made it all the more impactful. She was born during the “special period”—an extended economic crisis with widespread food insecurity that lasted for about a decade in the ‘90s after the Soviet Union collapsed. People we met talked about this period openly and often—it would come up when we asked a question like, “How long does it take to commute into the city?” and an answer would be given in two parts: how it is now, and how it was then. Even though it ended a quarter-century ago, it still feels very fresh in the collective memory. 

Cuba’s agricultural sector expanded a lot after the special period, as the country had to rely more on what they could grow when imports from the Soviet Union stopped. Most of the food is organic and very local by necessity (pesticides and chemicals are expensive and hard to come by), and there is an emerging food scene that was truly one of the highlights of our experience. On our first day we had lunch at El Café, a bright space with tall ceilings and a rare (for Cuba) vegan-friendly menu that could hold a candle to the trendiest spots in Los Angeles. From there we wandered into Clandestina down the street, which is proudly Cuba’s first independent fashion brand. The owner, Idania, something of a local celebrity, popped out and greeted Tegan like an old friend. We saw Idania a few more times throughout the trip, at a party in a warehouse with a New-Orleans style brass band, and a rooftop dinner on our last night. It’s clear that her brand is in with Havana’s cool crowd, and every room she entered was enlivened by her presence. If you visit, you have to go to the Clandestina storefront in Old Havana to get one of the maps of their favorite addresses in the city, which will have the most up-to-date intel on where you should eat (El del Frente and Antojos), drink (El Dandy and Melodrama), and dance (Fábrica).

On another day, we woke up early to head west to the Viñales Valley. After a three-hour drive, we mounted horses and trotted down a short trail to a farm where a handsome Cuban named Carlos, who revealed the most blindingly white teeth between puffs of a cigar, shared that his family had been growing tobacco here for years. However, since the government takes such a high percentage of the crop, they also grow corn, coffee and vegetables, raise animals, keep bees and make a special type of rum from the Guayabita del Piñar fruit. Though it was barely 11 am we had to sample some, and it was truly the best rum I’ve ever had. Carlos rolled a few cigars and artfully wrapped them in a dried leaf for us to take home. Then it was back in the saddle (with a bit more liquid confidence this time) to head to lunch. 

One of the most cinematic scenes from the trip was emerging from a wonderfully overgrown horse path to a clearing where a small restaurant sat as if it were waiting there just for us. It was framed so perfectly by the mountain behind it that it looked like a still from a Pixar movie. We plopped down at a long table out front and ordered one of everything on the menu from Berta, the elegant owner of the farm-to-table restaurant El Cuajani. As she passed plates of fish croquettes or delightfully simple green salads around the table, she would chime in on our conversation with an anecdote about her time living in France, or studying Chinese in university. By dessert, we needed to know more about her compelling background and how she started this fairytale-like outpost in the mountains of Cuba. She explained that she and her husband both left Cuba decades ago, but decided to come back years later for a more pastoral life and the chance to build something in their home country. Throughout the conversation, she casually mentioned that her friend José (by which she meant the chef José Andrés), who she’d worked with while she supported World Central Kitchen during Covid, had stopped by the other day. And when she heard that my friends lived in The Bahamas, she recalled that her daughter was friends with Lenny’s (yes, Lenny Kravitz), and had spent time on an island called Eleuthera. Small world. We ended the meal with hugs and rich cups of home-grown coffee before driving back to the city. Still full from lunch, we headed to Bar Melodrama that evening for some lighter fare (get the empanadas!) and mojitos to end a great day.

We spent the next few days in the city doing everything from a rumba dance lesson to a block-printing workshop, visiting another farm, touring markets and taking walks along the Malecón, a long esplanade/sea wall nicknamed the “sofa of Havana” for its hang-out crowds. Our last day was spent at Santa María del Mar, a long stretch of beach just 20 minutes east of Havana. On a stroll down the shoreline we came across a humble beach cafe, where we sat at one of five white plastic tables shaded by palm fronds and listened to a live band play covers of Buena Vista Social Club. They served no water—unless you wanted to drink it straight from a coconut—only piña coladas and simple dishes of grilled fish or chicken. I didn’t see a sign and don’t think it had a name, but if you wander long enough you’ll know when you find it.

Logistics

Visas – Travel restrictions for Americans have changed many times over the last few years. Obama famously “thawed” restrictions, which Trump promptly refroze. Currently there are 12 categories of travel that allow Americans to visit Cuba, the “Support for the Cuban people” being the only type of visa that average travelers qualify for. Other categories are reserved for visiting family, religious travel, journalism, etc. Wanderers Club took care of everything in this regard. I sent them my passport information and two weeks later, my visa arrived through the mail. Then 48 hours before I took off, they emailed me the forms I needed to show at the airport. Seamless! You can still plan your trip without an agency by purchasing a visa online through Cuban Visa Services, or through the airline you are traveling on. And while non-stop flights from larger hubs like NYC haven’t resumed, there are daily flights from Miami to various parts of Cuba on most major US carriers. 

Cash – Your credit/debit cards will not work in Cuba, so you need to bring cash to exchange. Bring more cash than you think you will need, because there is no way to get more if you have an emergency, or want to bring home some rum, coffee and cigars—which you will! Wanderers Club advised us to bring $500 USD each for the week, I think I ended up only spending $200 (though all of our transportation, tours, and most of our meals were included in the cost of our trip—prices start around $4,000 for a week, including flights). I found that more places were willing to accept USD or euros than I was expecting, but the norm is definitely to pay in CUP (Cuban Pesos). The exchange rate is constantly changing—it fluctuated from 240 to 265/dollar in the course of the week we were visiting. Luckily, Gaby took care of exchanging cash for us so we didn’t have to stress about any of that. 

Internet – One of the best parts of this trip was being able to unplug for a few days. That said, if you do need to be online it is possible to stay connected. Most hotels and some rentals have wi-fi, though it’s not particularly reliable. Also many websites and even Spotify are blocked, so it would be helpful to download a VPN in advance. As for cell service, don’t bother using an international data plan on your phone—the coverage and fees will be terrible. If you need data on your phone, you can purchase a Cuban SIM card once you arrive, unless you have a newer iPhone that uses an eSIM, in which case you should just set an OOO and enjoy being offline.