Cuba
A four-day romance with an enthralling island.
Written October 2023
Field Notes
My family and I traveled to Cuba to celebrate my father’s 60th birthday with the things he loves most in life: Cohibas, colorful architecture, and his family, in that order. Cuba, blissfully cut off from the world, would allow us to step away from our phones and enjoy what English doctors once called ‘sea cures.’
The realities of the trip were immediately more complex than anticipated. There was Visa procurement (‘Support for the Cuban People’) to consider, as well as the inability to use our credit cards once on Cuban soil (we each took out $500 USD, to be safe). My sister tirelessly Googled government policies and legal spots to visit as Americans – a few more hoops to jump through than the average Caribbean vacay.
On arrival, we zipped around in classic ’50s mobiles, lounged in mansions, and appreciated the warmest hospitality on this planet. We rode horses, coughed on cigars, and clumsily salsa’d to “Guantanamera.” But mainly, we listened and empathized with our hosts as they shared the frustrations of daily Cuban life.
Our host, Daya, fretted heavily as she spoke of Cuba’s increasing emigration. Even her son had fled Cuba for Miami’s shores. Our guide in Viñales, Luis, expressed similar sorrows – all of his friends had left under Spain’s Golden Visa program. Our Old Havana guide, Leandro, made ~$160/month as a teacher, but used his tours as a way to fill his MLC card with foreign currency, support his mother, and buy chicken on the black market (His protein needs exceeded the government’s allowance).
Witnessing the dilapidation of this beautiful island is tough. There’s a lot to say about the fact that we, as privileged Americans, now get to occupy the mansions that were once ripped away from wealthy Cuban families. Not to mention the actively harmful US-Cuban policies still in place. Grappling with these ironies is challenging — doing it while drunk off of Havana Club daiquiris is even more so!
Cuba is intense, elegant, devastating, vibrant, cruel, and completely enthralling. I hope you enjoy the ride.
Where to Stay
We stayed in a beautiful loft in Vedado, walking distance to the Malecón and a five-minute drive to Old Havana. Vedado, meaning “forbidden,” has a complicated colonial history, but now exists as a collection of stunning converted mansions — some into government buildings, some into casas particulares, which are private rooms rented out by Cuban locals who get to keep the profits.
There’s a reason our casa is so spectacularly reviewed. Our hosts, Daya and Lucia, were incredibly warm and chatted with us for hours. Miriela, our chef, whipped up stunning Cuban breakfasts and snacks. It was truly a blast just to stay home and drink mojitos, gorge on freshly-fried croquettes, and replay the day’s adventures on the balcony.
Day 1
Arrive at José Martí airport around mid-afternoon and get whisked away by some cabbies in cars that should have been retired 50 years ago. Seriously, these things can’t do more than 25mph. Put your stuff away at your casa particular, unless you’re staying at a state-sponsored hotel. Stroll over to El Malecón, an open-air seawalk, for spectacular sunset views. This part gets tricky – you’ll need to summit Hotel Nacional de Cuba to get to Bar Capablanca, where you must bargain with waiters to use their Cuban credit cards in exchange for cold hard plata. But the panoramic views are worth it. Get dinner at Paladar Café Laurent and call it a night.
Day 2
Brunch it up in your casa before setting off on a walking tour of Habana Vieja. We thoroughly enjoyed hanging with Leandro, who kept it short, sweet, and real. Engage in classic walking tour rituals (stopping at Cuban cigar stores, hiding from the sun). If you see the naked woman riding a rooster, you’re almost done. Hit up some nearby cafés for a much-needed caffeine boost. If you’re feeling touristy, head over to Bodeguita del Medio, birthplace of the mojito, or El Floridita, where Hemingway famously pounded daiquiris on the regular. For dinner, you’ll be dining on a stunning terrace, El Cocinero, followed in close succession by dancing at Fábrica de Arte, Havana’s premiere nightclub-slash-art gallery-slash-event space. Sleep peacefully – you earned it.
Day 3
Today we’re going to Viñales Valley on a day trip, as we’re on a tight schedule, though you can definitely stay overnight. This UNESCO World Heritage Site is like waking up in Jurassic Park, except instead of dinosaurs you’ll find 60-year old Cuban men who have been smoking cigars since they were 10. Here, you’ll drink homemade piña coladas, ride horseback through tobacco fields, and meet Don Pepe, a Cuban icon. Then, you’ll have the most filling Ropa Vieja (shredded flank steak) followed by cave tours where we found actual dinosaur bones yet to be reported to authorities. Take a nap on the two-hour drive back to Havana, and head to local dining spot La Bodega de Reserva.
Day 4
After three jam-packed days of touring and eating, it’s time for… more touring and eating. Just kidding, we’re headed to the beach! Santa Maria del Mar, to be exact, which is only 30 minutes from Havana as opposed to a few semi-nicer beaches two hours away. But this one serves your purposes perfectly, with turquoise water and friendly servers armed with rum. After lounging, we’re putting you to work. Grab a partner and head to La Casona del Son, where you’ll be subjected to brief mortification as you learn the basics of salsa – you won’t forget them soon. Finally, head back to your casita and as they say in NYC, “enjoy your rent” with a private chef, Rosie, cooking you a deluxe seafood dinner. If you’re not staying with the hosts I presented earlier, feel free to riff this night. Fly out the next morning, wishing Cuba a tearful adiós.
