One recent night in Havana, I stared out the window of my friend’s house in the now faded middle-class Vedado neighborhood. A weary 1956 Chevrolet Bel Air wheezed past, trailed by a beaten-up Soviet-era Lada taxi rattling over the potholes. The air smelled sweetly of mimosa and, vaguely, mildew. Wooden window shutters creaked on rusted hinges, brushed by a cooling breeze sweeping in from the sea.
“I want to live here,” I said with a sigh. My friend Mari turned to me. “Why not marry Jessica?” she asked, speaking of her teenage daughter. She didn’t appear to be joking.
Cuba constantly delivers such curve balls. Whenever I’m in Havana, I feel as if I’m living inside either a swoony novel or a Hollywood thriller.
Mari’s shocker sent me in search of a drink. I headed to the nearby Hotel Nacional for a mojito and cigar (like Che Guevara, I prefer Montecristos) at the open-air terrace bar, where a five-piece band spiced things up with hot salsa. The landmark 1930s grande dame is still the preferred hotel for visiting bigwigs—Lucky Luciano famously called a mobster summit here in 1946, ostensibly to honor an up-and-coming singer named Frank Sinatra.
My favorite nightclub, Gato Tuerto, is down the hill on Calle O. This tiny 1950s supper club has been spruced up for tourist consumption, but patrons are mostly Cubans and local expats, and I still sense that Sinatra and his Rat Pack might saunter in.
Gato Tuerto reflects one of Havana’s unique enchantments: its aura of pre-revolution redux. Throughout the city, retro nightclubs, worse-for-wear Detroit imports, and grimy advertisements for Hotpoint and Singer on weathered facades cause double takes.
I recently hailed a colectivo (shared taxi)—every visitor should do so—and jammed in with six Cubans as the circa-1948 Cadillac cruised down Avenida Linea to the rhythm of a rumba on the radio. My destination? El Cocinero, one of Havana’s trendiest paladares (private restaurants).
A spiral staircase corkscrewing up past a redbrick chimney spilled me onto the chic rooftop restaurant. I savored gazpacho, goat-cheese baguette, and garlic octopus tapas alfresco. The city’s young farandula (bohemian in-crowd) chatted over cocktails before streaming downstairs to the adjoining Fábrica de Arte, an avant-garde cultural venue that wouldn’t be out of place in New York City’s Meatpacking District.
Don’t believe anyone who tells you Havana is sclerotic. Or, worse, that the food is boring. Chic clubs and paladares have blossomed since 2011, thanks to Raúl Castro’s economic reforms, bringing heapings of style and good food.
But most Cubans are too hard up to partake of Havana’s new “middle class” spots. The city is best appreciated on their simple terms: the farmers markets, such as at Calles 19 and F, displaying mini-mountains of guavas, marañons, and other tropical fruits; the youth gathered on the seafront Malecón promenade at night, gossiping and flirting over shared bottles of rum; or ice cream enjoyed beneath the dappled shade of jagüey trees drooping their aerial roots to the ground at Parque Coppelia. Everyone stands in line at Coppelia (supposedly the world’s biggest ice creamery).
I love strolling along Vedado’s Calles 17 and 19, lined with beaux arts buildings such as the Museo de Artes Decorativas, lavishly embellished as if the prerevolutionary countess owner were still there; and the mansion at Calles 19 and H that houses UNEAC (National Union of Cuban Writers and Artists). Ground zero for intellectual life in Havana, UNEAC hosts regular peñas—musical and literary gatherings.
Then there’s the six-lane Malecón boulevard stretching along the Atlantic seashore, linking Vedado to Habana Vieja (Old Havana). It offers a microcosm of Havana life: cigar-sellers, fishers casting off from giant inner tubes, musicians practicing guitars and trumpets. Since I usually have camera in hand, what should be a 30-minute stroll can take me half a day, so many are the distractions.
Habana Vieja preserves one of the great historical cities of the New World. Castles, convents, and palatial mansions dating back centuries still reign majestically over plazas and cobbled streets haunted by the boot steps of conquistadores and, infamously, by Ernest Hemingway’s ghost.
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Visiting friends invariably ask me to guide them to Bodeguita del Medio, a graffiti-strewn bar where Hemingway is said to have supped mojitos: The reality is that he rarely drank there. It’s a stone’s throw from Plaza de la Catedral, with its 18th-century baroque cathedral.
Off the plaza’s southwest corner, on Callejón de Chorro, is Taller Experimental de la Gráfica, a graphics cooperative where artists engrave and print one-of-a-kind pieces on antique hand-primed presses. While here, I usually call in at Dulcería Bianchini, a cubbyhole coffee shop where Italian-Swiss owner Katia serves too-good-to-resist croissants, quiches, and tarts, plus frothy cappuccinos.
One of my favorite paladares—Doña Eutimia—adjoins the workshop. This is the place to enjoy down-home creole cooking, such as ropa vieja (braised meat prepared with garlic, tomatoes, and spices) served with hills of white rice and black beans.
A few weeks after Mari’s indecent proposal, I am back in Havana and pay a visit. To my relief Mari tells me that she and her husband, Jorge, have reconsidered having me marry Jessica. Then she throws me another Cuban curve ball: “Jorge and I can divorce and you can marry me.” I smile. With an urban culture as eccentric and enigmatic as this, no wonder I find Havana one of the most engaging cities in the world.
This piece, written by Christopher P. Baker, an expert on our Cuba trips, first appeared in the May 2015 issue of National Geographic Traveler.