As the U.S. restores its relationship with Cuba, the world awaits a country on the verge—but of what? Gary Shteyngart discovers a culture that is hanging in the balance, at turns strivingly modern and forever 1959.
Cuba, Cityscape
Credit: Frederic Lagrange

Just 45 minutes out of Miami, about the time it takes to fly from New York to D.C., I am on a chartered jet circling over an island, a nation, and an idea. American tourists, some old enough to have been adults during the Cuban missile crisis, are leaning into their windows, adjusting their thick glasses to take in a landscape of tropical greenery dotted with Soviet-style apartment complexes and fiery Socialist slogans. Our Cuban-American counterparts come loaded with loot for their relatives; one middle-aged man is wearing a Hello Kitty backpack on his shoulder, the price tag still attached. Soon we are taxiing to the terminal past Russian-made Cubana airliners, barely up to the challenge of taking to the skies. The country that has played such a ridiculously outsize role in the American imagination is right here before us, lush and threadbare, beguiling and humdrum, proud and ruined.

Let me mention the date before I continue, because when it comes to Cuba, dates matter. Today is January 9, 2015, 24 days since President Obama announced his intention to restore diplomatic relations with this country. And although I’m only set to spend a week here, I will leave a slightly different place from the one first glimpsed outside the airplane window.

But I shouldn’t get ahead of myself.

Back on January 9, 2015, the chief legal way for a U.S. citizen to travel to Cuba—other than for Cuban-Americans with relatives on the island—was through one of the people-to-people exchange programs sanctioned by the Treasury Department’s Office of Foreign Assets Control. These group tours are designed to “result in meaningful interactions between the U.S. travelers and individuals in Cuba,” which in practice means lots of rumba classes, art gallery visits, and the most dreaded word in tour group vocabulary: flamenco. And so I find myself on a Chinesemade bus surrounded by boisterous, mostly older American tourists about to undergo a week of jam-packed cultural exchange. We are at the airport’s parking lot, waiting for everyone to clear customs and clamber aboard. Across the lot, a red-and-white 1950s Chevy Biscayne is taking an hour to huff into its parking space, while a father wearing a shirt with the Chevy logo throws a weathered baseball around with his kid. It’s not just the cars that evoke midcentury America; the entire pace of life seems closer to the Eisenhower era than to the Zuckerberg one.

For a travel writer, being forced into a tour group instead of being allowed to roam free is like giving a dachshund long legs—life is easier, but you’re not yourself at all. Our leaders are a charming young American named Tony, who wears a newsboy cap and rockabilly sideburns, and his Afro-Cuban companion, an even younger woman named Yanet. Our driver is called Bistec, because his earlobes hang down like steaks.

“Fidel is still alive!” Tony tells us as we rumble out of the airport parking lot. A rumor had circulated among the masses of Cuban relatives outside the terminal that Castro had finally departed for the Leninist version of heaven, a produce store stocked with a few heads of lettuce.

“Welcome to our planet,” Yanet says, gesturing at the nearly empty highway on the approach to Havana. I notice an Apple logo on a 1950s Chevy. You can’t say the Cubans don’t have a sense of humor.

The buildings—jumbles of Neoclassical porticoes and dashes of the Baroque—are weather-beaten and partly hollowed out. “It’s a tragically beautiful city,” Yanet says, and I’m reminded a bit of Leningrad, the city in which I was born, during the decline of the Soviet Union. There’s a lushness to this decay, the jerry-rigged lifestyles, the queues outside government office buildings where the basics of life are parceled out in monotone by tired bureaucrats, the carelessness with which black electric wires drape a fading mansion, the orderliness of red-and-white-uniformed students lining up before a school.

We pass the hulk of the former National Assembly, meant for a nation of several hundred million people, not 11 million, and pull up to the Parque Central, a banal hotel that seems to accommodate almost every American tour group on the island. On the rooftop, we are given the traditional Cuban welcome for all gringos: a volley of mojitos and cuba libres, which, because of the embargo, are mixed with TuKola, the Socialist alternative to Coke.

We introduce ourselves. We are investment banking professors with handkerchiefs tucked into our blue blazers; we are Pilates enthusiasts from Ohio; we are doctors and lawyers and one former Pan Am flight attendant. And everyone is here for pretty much the same reason. We are Americans fascinated by the very thought of a sunny Marxist dictatorship floating off the Florida coast.

The tour group heads off to witness a display of Cuban dancing at La Casa del Son, just a few blocks away from the hotel. We are soused down with the requisite cuba libres, and then some gorgeous young women in black minis spin around for us. A dude in a 70s leather jacket with spiky 80s hair shows off his moves, as well as the fact that Cuba’s stylistic choices are a museum of four American decades starting with 1959 and ending some time around Lenny Kravitz’s debut album. When we’re invited to salsa (“Try? You must! No? You don’t want?”), I duck out and take my first walk alone.

Havana: Where the streets have no lamps. It’s only 7 p.m., but the city is lost to half-darkness. A staircase meanders into a former manse, its columns dense with wires like a form of vegetation. A store, half-lit, seems to be selling nothing more than a single box of detergent. The only well-lit portal is the window of a local administrative office from which Che Guevara’s youthful visage admonishes passersby to “work more and criticize less.” I can hear my tour group rumba-ing somewhere down the street, but suddenly I realize the following: My iPhone doesn’t work here. My American credit cards don’t work here. There is no traffic. There are, practically speaking, no stores. There is no light. I am standing in a city virtually untouched by the dense web of satellites floating above the earth. I am primordially happy.

Cuba, Buildings
Credit: Frederic Lagrange

Frédéric Lagrange

The following day, we’re on the bus, stopping at an art museum and a paladar serving fresh but pointless mahimahi. Paladares are the new wave of privately owned restaurants housed in shabby-chic quarters, and last night we’d dined at our first one: La Guarida was a plush and cinematic place with starchy food that failed to impress. (Then again, coming to Cuba for the cuisine is like going to Boston for the nightlife.) As our fearsome Chinese-made vehicle groans on through the potholed streets, my snout is pressed to the window, and I’m dreaming of being let loose upon Havana. How ironic that a U.S. law designed to combat the Castro regime actually restricts the movements of Americans on Cuban soil.

On that note, we arrive at the Museum of the Revolution, a grand mansion in which the pre-Castro dictator Batista was nearly assassinated. After touching the golden AT&T phone once gifted to the overthrown leader, I sneak away from the group to commune by the museum’s Wall of Cretins. Like many ideological displays in Cuba, the Wall is a perfectly distilled cocktail of pride and spite, featuring cartoonish renderings of Ronald Reagan in a cowboy hat, George Bush I in a Roman toga, and W. in a Nazi helmet reading a book upside down. It’s crude and childish, but the Cubans seem to have a lot more fun with their propaganda than their counterparts in Pyongyang and Tehran—more “you silly imperialist pigs” than “death to the great Satan.”

And then a wonderful thing happens: Tony the tour leader lets us roam free. I quickly run to the Malecón, the seawall upon which half of Havana’s population seems to stroll—it has been referred to as “Havana’s sofa.” The decayed rocks of the seawall form their own compromised skyline, mirrored by old mansions that look like they’ve been eaten away from the inside, their exposed innards forming so many Escher drawings. How soon, I wonder, before this prime real estate is turned over to a string of Marriotts catering to the expected 3.5 million American tourists?

Back in Old Havana I spend about 30 minutes waiting for some simple but delicious churros topped with condensed milk from a street-side stand, worrying along with my Socialist compatriots that the vendors will sell out before our turn comes. As night descends, I pass through dim streets punctuated by pockets of heat and sound, past a first-floor party bursting with reggaeton, past grandmas sitting on their rocking chairs like exhibits in a museum of working-class life. Without the distraction of an iPhone, I can take time to soak in my surroundings. Although it’s a city, there’s the feel of a half-ruined village. I spot some kids lobbing a soccer ball into the impressive façade of the Numismatic Museum—a hilarious concept in a country where most workers are paid in a near-worthless currency and tourists spend “convertible pesos” pegged to the dollar.

Deep into the night, on a completely dark street that in most Latin capitals would carry at least a sliver of danger, I can feel the presence of a very young woman walking beside me. “Chica,” she hiss-whispers at me. “Chica! Chica! Chica!” I make a helpless mooing sound and run away from her, my wallet, stuffed with convertible pesos, sweating in my jeans.

Our next tour is of the leafy Miramar neighborhood. The city’s wealthy gradually ventured beyond Old Havana and the adjacent bustling Centro district, moving out to Vedado, Miramar, and then Miami. To explain: Vedado is the central core of the city, with famous buildings like the midcentury Habana Libre hotel and the enormous Art Deco Hotel Nacional; Miramar has a mansions-in-the-suburbs feel; Miami is a nearby city where the relatives of people in Miramar and Vedado get them their used iPhone 3s.

Cuba, Tobacco Fields
Credit: Frederic Lagrange

Frédéric Lagrange

Today’s paladar, Río Mar, is probably my favorite of the trip. The pretty view is of the mouth of the Río Almendares, the river that separates Vedado from Miramar. There are some wealthy Cuban-Cubans, Louis Vuitton handbags hanging from their chairs, along with Cuban-Americans taking their kin out for lunch. The holy trinity of mojito, crudo, and flan are a touch better here than at other paladares, and an appetizer of smoky chorizo and beans has a hearty peasant flavor.

Afterward, I ask our driver to drop me off in the middle of Vedado to visit a friend of Rosa Lowinger, a Cuban-American art conservator I know from the States.

José Alberto Figueroa, an important Cuban photographer, and his wife, the curator Cristina Vives, have turned their home into a salon for the visual arts. Figo, as he is known, has a graying beard and is wearing a light jacket in the mild tropical heat. The apartment he shares with his wife is possibly the most tasteful in the Western Hemisphere, somehow full of both light and sympathy. It is, however, still located in Cuba, so while the bathroom contains an issue of Marie Claire, its toilet still has to be activated with a spigot. Sitting on his balcony, I drink a strong Bucanero beer, while Figo smokes an equally strong Popular cigarette. We talk about the projected millions of American tourists who will soon descend on his nation. “Mariel is a port big enough for a mega-cruiseship,” he says, in a tone more wistful than weary.

Nearly all the walls of the apartment are covered with art, including works by the wonderfully wiseass Alejandro Gonzáles, who has a series of sparkling photographs of megaprojects the Cuban government never finished, such as the ghostly Juragua nuclear power plant decaying somewhere off the coast. The idea of mega-cruise-ships in a country with, at best, a mid-20th-century infrastructure is surreal yet fitting for a nation that could copyright the term contradiction.

The most striking photograph is a simple black-and-white taken by Figo from the terrace of Havana’s airport, eight years after Castro came to power. His mother, a tiny figure in a black dress and heels, is waving good-bye to Figo from beneath the fuselage of a Cubana jet. She is headed to Miami and, because he is of military age and not allowed to travel, Figo will not see his mother for the next decade and a half. Figo has given this melancholy series of photographs a simple title: Exile.

On the way down the staircase and into the humid Havana night, Figo tells me, “We have to open up to the world. There’s no other way.”

The next day we take a two-hour bus ride to the Viñales Valley, in neighboring hurricane-prone Pinar del Río province. It’s famous for its tobacco, verdant hills, and mogotes, the magnificent limestone mountain range that looks like the plates and spikes of a stegosaurus’s back. Vast stretches of the main national highway are all but car-free; at one point I see a woman walking with a stroller down the middle of Cuba’s version of I-95.

After a lunch of roast chicken, fresh cabbage, and plantain chips at a local tobacco farm, I take a solitary stroll down a slight hill to the colonial town of Viñales. The countryside offers a brilliant panorama of both happiness and want. The red earth is full of budding tomatoes and black beans. Dark brown streams are filled with happy piglets, and an oxen pulls a canister of water on a pallet. I see a boy bike down the hill balancing a giant bottle of TuKola on his pumping legs. An escaped goat chews on a palm leaf. A man talks violently to his horse. On the main plaza, chickens waddle past a statue of José Martí, Cuba’s omnipresent national hero.

The country’s panoply of cars are on full display here: the bulbous 1950s Chevys, the boxy Soviet Ladas, and the utilitarian new Chinese Geelys. Surrounded by American, Soviet, and Chinese influences, it’s not hard to conclude that Cuba has been bouncing between empires for far too long. Can a nation living under an endless series of slogans, with an endless list of enemies and comrades, heroes and betrayers, ever escape into the mundane?

On a day with no people-to-people exchanges, I finally meet some actual people. Let’s call one of them Mago. He’s in his late twenties or early thirties, another friend of Rosa Lowinger, who described him as “a hipster who wants to work in film.”

My Spanish is nonexistent, so I can understand about 20 percent of Mago’s English, which is fine, because the other 80 percent would probably blow my mind. The oft-repeated phrase “Cuba is crazy” is the one thing I get completely.

His apartment in Vedado—another white-walled, art-filled space—is packed with a motley assortment of edgy Cubans: a cool young photographer, a physical therapist, a taxi driver who also doubles as a pot dealer. We drink Beefeater gin neat, while all around me the semiofficial pronouncements of Cuba’s being a drug-free country are dispelled.

“How much does a physical therapist earn in America?” the physical therapist asks me through the smoke. I give him an approximate figure, and he looks at me with a knowing sadness, his mind spinning with hard currency. The average official salary for a Cuban is around $20 a month.

Cuba, Landscape
Credit: Frederic Lagrange

Frédéric Lagrange

The pot-dealing taxi driver takes us to Old Havana in his stuttering, fume-belching 1950s Plymouth. Mago and an Afro-Cuban friend I’ll call Mikey, who has lived on 183rd Street in New York, take me to a restaurant called O’Reilly 304. The place is blazing, full of Spanish tourists and locals, and we hang off a little ledge out on the street, eating ceviche and empanadas, drinking enormous gin and tonics packed with rose petals. We do what men do the world over: compare our sneakers and iPhones and talk blindly about the difficult past, which, for Mago, I believe, has included a stint in jail and several years of sweeping the streets as part of his parole. The young owner of O’Reilly’s pops out; he seems to know every single denizen of the street. He sports a Los Pollos Hermanos T-shirt, a hip reference to the Breaking Bad TV series. We’re finally seated next to two of the most beautiful women in Cuba, snacking on tuna tataki and croquetas.

Later, as we’re walking toward the Malecón, two cops stop Mikey for the Cuban version of a stop-and-frisk, which takes more than 20 minutes. Mago whispers to me that Mikey has been singled out for being black. When we finally settle down on the seawall with a couple of cans of Bucanero beer, Mikey points to the HABANA LIBRE sign blazing in the night above us.

“Havana never free,” he says.

I promised you I would fly into one Cuba and fly out of another, and today, January 15, 2015, one more pillar of the U.S. embargo of Cuba crumbles. The Obama administration says U.S. citizens will no longer have to ask permission to travel to Cuba (though you still need a visa). Restrictions remain in place, but Americans who wish to sample the island will now be able to do so on something of an honor system. And starting tomorrow, Americans will be allowed to bring back $400 in Cuban products, including $100 worth of Cuban cigars and alcohol. (The tiny gift shop of the Parque Central is immediately overrun by Americans.)

The days of the mega-cruise-ships from Miami docking at Mariel harbor are still years, maybe decades, away, but the door to Cuba is softly creaking open. A cab driver tells me that all the changes in U.S.-Cuban relations will be good “para usted y para nosotros.” He cheats me out of three convertible pesos, but I suppose that just makes him a good capitalist, too. “Cuba’s the most capitalist country in the world, in my opinion,” my friend Rosa had told me. “Everyone’s got an angle.”

On my final day, on the advice of Figo, I leave central Havana behind and take a taxi to the southern part of the city, along a wide boulevard called Diez de Octubre. In this, one of Havana’s oldest districts, grand balconied mansions hover over the street, nearly toppling from the weight of the laundry heaped upon their railings, as abuelas peek out from columned porticoes. Fierce curbside games of dominoes clack along in view of faded buildings with names like Apolo and El Grande. The state is everywhere, but the state is often exhausted: two cops, a man and a woman, push a Soviet Lada marked GUARDIA OPERATIVA down the thrumming boulevard. At a classical mansion housing a casa de cultura, elderly women practice to the sound of a piano, the halls reverberating sweetly with their voices at five in the evening. At the moment, all of Cuba seems ensconced in the sorrow and beauty of their song.