Cuba at the crossroads

In the wake of new diplomacy, a glimpse of island life at street level


This was my father’s car, and now it is mine,” says our taxi driver. “And this is my son, and he will start driving it soon, too.” He nods toward the dark-haired boy in the front passenger seat.

My 14-year-old son and I are in Cuba in mid- June, rattling in the backseat of a 1950s Buick headed for Central Havana. We’ve brought a rolling suitcase and a backpack stuffed with toothbrushes, pencils and medical disinfectant wipes to distribute — everyday items hard to come by in this island country.

Two months ago, I’d stood in my kitchen contemplating a new journalism project. My son was finishing eighth grade, hurtling toward college and independence. I’d started hoarding his childhood, stacking up memories against the future. We were heading to Cuba soon, and it seemed perfect. President Obama had recently announced intentions to normalize relations between our governments. If diplomacy was an instrument, he’d just plucked the string connecting Cuba to the U.S., and I’d be observing the vibrations in this former Caribbean paradise.

Paradise. I look around uncertainly as our driver negotiates Havana’s rush-hour traffic. My son and I have just shared a 50-minute flight with a handful of foreign backpackers and a Cuban-American family transporting Tide, an air conditioner and tires to their relatives. They’ll need them. The streets here are studded with potholes. Pedal taxis weave between old American cars, East German Trabants and the odd Peugeot. Cuba’s roads are a time portal to 1959, when Fidel Castro led a socialist revolution and received an American embargo in return. Despite this, our own taxi isn’t in bad shape. The seat springs may have collapsed in the Carter era, but the air conditioning is a godsend.

We unload at one of Cuba’s government-run hotels. I’ve constructed a general itinerary: Havana first, then a visit to the 16th-century town of Trinidad. From there we’ll head north to the agricultural town of Viñales. I plan on using the Internet to fill in details as needed. My guidebook has assured me that Internet access is available at hotels, but when I question the receptionist about it, she shakes her head.

Our room is simple but clean, the decor more inviting than I’d expected. Breakfast is served on the balcony in view of Havana Harbor. My son can sleep like a champ, but we’ve agreed on a reasonable wakeup time. We stock up on bottled water, then set off for Central and Old Havana. The city’s streets are packed with ornate buildings, signs of the country’s former gilded age when sugar funded a robust economy. The world is condensed here, the neighborhoods a collective endeavor of Moorish, French, Baroque and Art Deco influences. There’s opulence in some places, a faint sheen of Hollywood that evokes the days when the plush Hotel Nacional de Cuba attracted patrons like Sinatra and Winston Churchill.

Painted tiles, elegant columns and wrought-iron balconies are standard fare, as are pastel colors.

I’ve never seen colors being more completely themselves: rich orange, sunset pink, a blue so pretty and light it makes you thirsty.

The effect is part Arabian Nights and part fairytale, and I’m enchanted.

I look over at my son. He’s recently taken an interest in photography, and he’s busy positioning his iPhone. A Buick’s sparkling hood ornament; a dog dressed in hat and bowtie to solicit tourist dollars; a produce stand with plantains dangling like crescent moons. He collects these images on his camera roll. Later we walk down the Paseo del Prado, a tree-lined street reminiscent of a sweeping Parisian boulevard. It stretches to the Malecón, the five-mile-long sea wall bordering Havana’s coast. I take a picture of him gazing out at the harbor that once braced against pirate ships and bade farewell to ships bound for Spain.

Cuba has not been entirely cut off from the world, of course, despite the 1960 American trade embargo, but there’s a palpable air of isolation here. Many walls are literally crumbling, their wires exposed like loose stitching. The few shops we see are sparsely stocked: bottled water, rum, nail polish. The Cubans we meet are excited to learn we’re Americans. We think more will come! they tell us. They sit on stoop after stoop in their neighborhoods, and I can’t tell if they’re content or daydreaming of an alternate reality. In the meantime, street bands fill the air with the sounds made famous by Buena Vista Social Club. There’s a subtle thrum of gritty celebration, and I’m dying to dance.

We discover Internet service inside the lobby of the upscale Saratoga hotel. For $6, we receive one hour online. It’s too slow for downloading television shows, and my son is stuck watching the same two old episodes of The Walking Dead on his laptop each evening. I search TripAdvisor for restaurant advice. Fidel Castro’s brother, Raul, became Cuba’s President in 2008. His limited support of private enterprise has inspired the establishment of paladares throughout the country. Family-run restaurants that serve homemade Cuban food, paladares primarily operate out of family homes, serving guests at tables laid with mismatched tablecloths and silverware. These are heavily reviewed on TripAdvisor, and we end up following a trail of the best paladares throughout our stay.

The food is delicious, consisting mostly of white rice, seasoned beans, roasted squash, steak and seafood. In the 1990s, to help address food shortages faced in the wake of the Soviet Union’s collapse, Cuba shifted its focus to organic food production and educated city residents on urban farming. One of the paladar owners tells us that most of the food comes from farmers’ markets. And because they can earn in one week what other Cubans make in a month, it’s no surprise when owners encourage us to recommend them on TripAdvisor after every meal.

Other entrepreneurial Cubans rent out guest rooms and apartments. The standard rate is $25 per night, total. Everybody seems to know someone who has one. Before we leave for Trinidad, our hotel receptionist calls a friend. Six hours and a sweltering bus ride later, we arrive at her house. Our bus was late, and she’s already rented the room. She introduces us to her neighbor, Jenny, and within minutes Jenny has stuffed her belongings into plastic bags and left us alone in her tiny apartment. We sleep on twin beds neatly made with lime-green blankets. The floor is tile, the bathroom barely big enough to accommodate the shower. The kitchen has a hotplate and a curtained cupboard beneath the sink, and I feel oddly like I’m visiting my grandmother’s house in 1970s Queens, New York.

Trinidad has none of Havana’s urban vibe, and I wonder if the news of shifting diplomatic relations with the U.S. has been absorbed here. This is a rugged town in the province of Sancti Spiritus. Founded in 1514, it’s now a World UNESCO Heritage Site. Built on profits from the sugar and slave trades, the town relies heavily on tourism. Busloads of European tourists spill into the open-air Plaza Mayor, which is rimmed with Spanish Colonial houses once owned by wealthy town residents. At night, live music pours through the grillwork of nearby restaurant windows.

We walk Trinidad’s cobblestone streets, passing rows of one-story pastel houses with terra-cotta roofs. Cowboys ride by on horseback while older men with sun-weathered faces sell bread from their bicycles. Above the Plaza is the Cathedral of the Holy Trinity, a 19th-century church with broad brown doors. We watch as a man in slacks and a button-down shirt sits on the front steps, arms slung over his knees, head bowed as if he’s waiting for something to happen. My son steps quietly in front of him and takes a picture.

We watch the sunset that night from the tower of the Museo Histórico Municipal. As the sun eases toward the horizon, it folds Trinidad’s sherbet-colored houses into its glare. They soon darken like an overexposed negative and disappear.

Our bus back to Havana gets a flat. While we wait for repairs, my son and I grab a ham sandwich from a roadside stand. We know it’s a mistake when our stomachs start to churn. Havana is oppressively hot, and we climb wearily to a third-floor guest room adorned with a plastic-covered couch and Santería dolls. I’m uneasy at the claustrophobic quarters but too sick to object. We sleep fitfully that night and resume our search for rooms in the morning. A pedal taxi driver named Alex rescues us from the sidewalk and offers to help, pedaling us to his friend’s apartment near the Paseo del Prado. It’s the nicest one we’ve seen, and we gratefully install ourselves there.

Motivated by our unsettled stomachs, we cancel our plans in Viñales and spend our final days in Havana. Now familiar with its neighborhoods, our eyes stray from street level to absorb other details. Images of Raul and Fidel Castro seem scarce, but Che Guevara’s famous visage is everywhere. An Argentine Marxist and Castro’s second-in-command during the Cuban Revolution, Guevara’s image appears on car headlights and on pins worn by city residents. Beneath his intense gaze, Cubans tell us excitedly that the American embassy is due to reopen soon. Most of them have a relative in the U.S. and say they hope to visit America.

In a shop in Old Havana, a man notices my Lonely Planet guidebook. He leans close. “Everything in that book is a lie,” he whispers. “They make it seem like our government is good, but they’re all liars. The Internet is coming soon, and then they’ll know the truth. Tell your friends.” He raises his head then and comments loudly on the weather.

On our last day in Cuba, we take a double-decker bus to the Plaza de la Revolución, the site of many speeches by Fidel Castro to Cuban citizens. Later, a taxi carries us beneath Havana Harbor to the dual fortresses of Morro and La Cabaña. Between them lie the remnants of the American U-2 spy plane shot down over Cuba while the world teetered on the brink of nuclear war during the Cuban Missle Crisis. They lie in a stark field, and suddenly the beautiful city my son and I have both come to love feels deeply weary and embattled. I feel weary, too, as I consider the many ways in which humans succeed in harming one another.

The U-2’s wing lies nearly flat on the ground as if it’s just spiraled down from the sky.

At 9 that night, the cannons sound loudly at La Cabaña. It’s a tradition dating to the 17th century, when Spanish colonial officials shot cannons to notify Havana’s residents that the city walls were opening or closing. Opening and closing, creating a world without and within.

Elizabeth Wolf is the director of a non-profit, a freelance journalist and resides in Boulder County with her son and their two cats. Carolyn Oxley is a Boulder-area freelance writer and poet. More of her writing can be found at

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