Smuggling a baby into Cuba requires a few simple things.
Well, first off you need a baby. Check. Then you need airline tickets to Mexico with a separate flight to Havana to skirt the U.S. travel ban. Check.
Third, you must be crazy. Check. It looks like we’re ready for takeoff.
I took the roundabout route to Cuba with my wife Sophie and our three-month-old son from our home in Washington, D.C. We took the trip because Sophie’s brother was getting married in Varadero, a narrow spit of luxury resorts and white-sand beaches that uncurls into the Caribbean about 100 miles east of Havana.
My wife is British and her family lives in England so it was easy for them. No trade embargo and a direct flight to Varadero. Time to relax on the beach and sip a mojito.
It turned into a Sisyphean ordeal for us, except Sisyphus had a crying baby strapped to his chest and he was endlessly circling a luggage turnbelt instead of toiling uphill. We suffered the full range of travel mishaps with airlines and hotels conspiring against us, but Cuba was worth the headaches.
Cuba is an amazing and confounding place, an anachronism writ large with 1950s American gas guzzlers, all chrome fins and coughing engines, sharing the road with boxy Soviet-made Ladas. The country presents a jigsaw puzzle of contradictions where the people love Americans even though America has turned its back on them for 50 years. It’s a place where hustlers, hotel maids, and taxi drivers can earn more than doctors because the tourist trade provides access to foreign currency. Most Cubans earn about $20 per month in government wages so a few dollars in tips can toss a life line.
Romantic images of Communism flower and die in Cuba, rotting on the vine as nostalgia for the revolution is weathered by harsh economic realities. Bubbles of capitalism keep surfacing and the Castro regime is struggling to contain the chaos, yo-yoing on whether to loosen free market restrictions. Congress is now considering whether to lift the travel ban and ease the trade embargo, a Cold War relic that has backfired and wounds the Cuban people more than the totalitarian government.
Despite the hostilities between our countries, I was touched by the friendliness of the Cubans we met. We enjoyed walking through Habana Vieja, the old town neighborhood of Havana where crumbling paint-chipped facades line cobbled streets that lead to the harbor and the cerulean sea.
Our son Soren was treated like a celebrity and kept turning heads in the street because there aren’t many fat, blonde, blue-eyed babies in Cuba, where there is a declining birth rate and an aging population. Smiling locals would playfully kiss his feet and say “Muy fuerte!” meaning very strong. At a bar in Habana Vieja, Soren took a turn on the congas when the drummer scooped him into his lap while the band belted Cuban ballads and dancers whirled to the lilting beat.
Lost Luggage and Missing Airlines
Our trip didn’t start well when we landed in Cancun but our suitcase didn’t. Our bag was stranded in Miami or it was leaving on a flight for its own vacation. We bought diapers, toothpaste, and deodorant at a gas station the next morning before boarding a ferry to Isla Mujeres, a less touristy island near Cancun. We sweated it out walking around town in our jeans before our bag arrived, just in time for our return trip to Cancun so we could catch our flight to Havana the following day.
That was the plan anyway. Cubana de Aviacion, the state-run Cuban airline, has a novel approach in the airline industry. They sell tickets for flights that don’t exist or they change the date without telling anyone. We arrived at the airport but the Cubana counter was empty. They had taken the day off so our tickets were useless.
That’s when my wife burst into tears, followed quickly by our baby. Sigh… But hope was on the horizon. Mexicana had a flight to Havana that was leaving in 45 minutes (sweet joy!) and a helpful Mexicana manager promised to do his best to get us on board. We bought new tickets and waited, and waited, and waited some more…
For some reason, Mexicana had to sell us paper tickets and then three employees hunched over a computer couldn’t figure out how to enter the tickets into their own system in time for us to catch the flight. So we got to spend more than eight hours in the airport with a sleepy baby waiting for the evening flight to Havana. It wasn’t as fun as it sounds.
Touching Down
Arriving in Havana at night was an eerie experience. The customs area was dark and foreboding, a dimly lit windowless space where employees wore surgical masks even though the H1NI virus had long since faded.
At the first checkpoint, the passport inspector wouldn’t let us stand together so I had to wait while Sophie held Soren up to a camera so their pictures could be taken. Cheese! We had bought Cuban travel visas which were stamped instead of our passports so there was no trace of our visit. Fidel may be famous for ranting against America but he does make it easy for Americans to slip into the country.
Fortunately, our suitcase arrived this time and we got lucky in customs. We pulled the “baby card” and a sympathetic guard let us skip the long line and exit into the airport without having our luggage ransacked. Sophie’s parents met us with a rental car and we slipped off into the rain-streaked night, straining to see the road on a winding journey that zigzagged through Havana before hugging the coastline toward Varadero.
As we neared Varadero, three women in short, skintight dresses teetered on high heels at the edge of the road, casting shadows from our headlights in the inky night. Sophie’s father didn’t see them so they hastily wobbled backward as we sped by. “You almost killed three hookers,” I said. “Did I?” he responded, looking over his shoulder. Maybe he shouldn’t be driving at night without glasses.
Varadero is a narrow peninsula lined with beautiful white-sand beaches stretching into the turquoise sea. The place is chockablock with resorts serving mainly Canadian and European tourists. We didn’t meet any Americans there, which wasn’t too surprising.
Sophie’s family and friends gathered in a gazebo on the beach for her brother Silas’ wedding. It was a moving ceremony with a beautiful bride and happy groom exchanging Cuban government vows that spoke of lifelong commitment and fidelity. Afterward, we smoked cigars, drank champagne, and danced to lively music from a salsa band.
The wedding was wonderful, but Varadero made me uneasy. The resort was a high-class bunker, a luxurious reservation for sunburned tourists that was isolated from the real Cuba. There was even a checkpoint and tollbooth on the mainland that kept most Cubans locked out of their best beaches. So much for the equality promised during the revolution.
The only Cubans in Varadero wear uniforms. Maids, cooks, and bartenders earn meager government wages and hope for tips to help provide for their families. We handed out generous tips and gave baby supplies to a pregnant employee who said diapers were impossible to find because of the U.S. embargo.
While the Cuban employees struggled to survive, we were downing mojitos and Cuba libres and stuffing ourselves at endless buffets with juicy prime rib and lobster in drawn butter. The uneven power dynamic carried a colonial vibe, and I was ready to head back to Havana after a few days in the sun.
Havana Bound
Back in Havana our reservation at the Hotel Inglaterra had disappeared and our pleas for mercy were met with shrugs and bored stares at the front desk. There really isn’t any incentive for good customer service if you make $20 a month and can’t be fired.
We had to pay double the previous rate and could only stay one night. We spent several fruitless hours the next day trekking to different hotels before finding a local travel agent. “It is very difficult to book a room in Havana,” he said but he didn’t explain why.
Founded in 1875, the Hotel Inglaterra is the oldest hotel in Cuba, an impressive neo-classic colonial building adorned with Spanish mosaics. The hotel has dark, dingy rooms with battered furniture and dodgy plumbing, but the location can’t be beat on the Parque Central. Next door is the ornate Gran Teatro theatre and the Capitolio, Cuba’s capitol which bears a striking resemblance to the U.S. Capitol down the street from our home in D.C.
We toured the Fabrica de Tobaco Partagas, a renowned cigar factory behind the Capitolio that produces immaculately rolled Cohibas, which cigar lovers dream of in America because they are banned. Photos weren’t allowed as we walked past workers hauling large bags of tobacco, sorting leaves, or rolling fat cigars on wooden desks in a long musty room where the sticky sweet smell of tobacco hung in the humid air.
Our Cuban guide was an engineer who moonlighted at the factory because he could make more from tips and discounted boxes of cigars than from his fulltime salary. He said factory workers have strict quotas of up to 250 cigars per day and inspectors examine every cigar for quality. He also was surprisingly blunt about the working conditions in the factory, where it appeared time had stopped in the 1950s without any advances in machinery. “This is not a good job and people do not last long here,” he said. “They only work in the factory if they cannot find anything else.”
Our guide also warned against buying cigars from hustlers on the street because counterfeit stogies are stuffed with tobacco stems or banana leaves. He said cigars should only be bought in official state-run shops, but I later saw him sidle up to a tourist in our group. “I can sell you a box of Cohibas at a good price,” he whispered. “I can give you the address to my apartment where we can meet later…”
Losing the Beautiful Ideal
Despite occasional hassles from hustlers, Havana is very safe, one of the few advantages of living in a police state where thieves and other criminals can receive draconian sentences after farce trials. Political dissidents often suffer the same fate, and international attention has been focused on recent hunger strikes by political prisoners and vocal street protests by their wives which triggered more arrests.
Times have changed since the heady days of the revolution when Fidel Castro, Che Guevara, and a small dogged band of soldiers led a popular insurrection that toppled dictator Fulgencio Batista’s regime in 1959. The uprising offers a textbook example of guerilla warfare with the outnumbered revolutionaries beating long odds by waging hit-and-run attacks on military garrisons and enlisting support from peasant farmers.
The revolutionaries issued the Sierra Maestra Manifesto in 1957 from their mountain stronghold. They said they were fighting for “the beautiful ideal of a free, democratic, and just Cuba” and they demanded democratic elections, the release of all political prisoners, and freedom of expression and the press. But all of those rights have been violated by the Castro regime. Substantial gains have been made in health care, education, and agrarian reform, but the revolution has come at a high price for the oppressed Cuban people.
In Havana, images of Che Guevara are everywhere, adorning walls, statues, T-shirts, tattoos, coins, and key chains. Nostalgia for the revolution is still strong, instilled through propaganda in schools and state-controlled media like the Granma newspaper. But the people appear ready for change and the government is offering some concessions. Residents can sell meals and rent rooms in their homes to tourists, and bus and taxi drivers pay taxes to run their own businesses. Cell phones are permitted and have become status symbols, but they are too expensive to use except for the occasional text so no one talks on them.
Lifting the misguided U.S. trade embargo would dramatically transform Cuba and push the Communist nation toward democracy by opening markets and placing more pressures on the aging regime led by Raul Castro, Fidel’s 79-year-old brother. The United States still won’t trade with Cub,a but China, which has a terrible human rights record on a much larger scale, is one of our biggest trading partners. The hypocrisy is glaring and the United Nations has passed resolutions condemning the embargo for 18 years in a row. The vote was 187-3 last year with only Israel and Palau supporting the United States.
Dollars, which were once the foundation of the underground economy in Cuba, are now penalized with an exorbitant 10 percent exchange rate surcharge, a backlash by Fidel Castro against renewed U.S. sanctions in 2004. We stocked up on euros before our trip because American credit cards are useless in Cuba.
Cuba now has a bizarre dual currency system with separate bills and coins. The Cuban peso used by locals is worth a few cents on the island and nothing outside Cuba. Tourists must buy Cuban convertible pesos, called CUC or “kooks,” which are worth about a dollar and have replaced the dollar in the underground capitalist economy.
We met a sad Englishman in a restaurant who said a Cuban man had promised him a much better exchange rate after he asked for directions to the bank. The naïve Englishman handed over 300 pounds and received a huge stack of bills, but they were the nearly worthless Cuban pesos. He didn’t know the difference until he tried to spend them later. In that one scam that lasted a few minutes, the hustler made more money than most Cubans make in a year.
Hounded by Hustlers
Hustlers called jineteros frequently tailed us, offering cheap cigars, fine food, or loose women. It was annoying and I kept waving them off, but one wily jinetero we met spun a more sophisticated spiel. He had a shiny bald head and wore wraparound shades, and he said he was a musician who played guitar with the renowned Buena Vista Social Club.
He said we could hear the band play in a hotel ballroom that night if we stopped in a bar so he could borrow a pen and paper. In exchange for the free tickets, he asked me to buy him a drink so we had a round of mojitos. Then he gave me a cigar and tried to sell a box of cigars. When I said no, he tried to extract cash with a sob story about needing diapers for his infant son. But when I pulled some diapers from our bag, he looked deflated and wouldn’t take them.
When the bill arrived, the waiter tried to extort twice the usual price for the drinks. At the same time, a tourist at another table was loudly protesting the price of his beer after another jinetero had lured him inside with a similar scam. The tourist stormed outside and found a police officer who wandered in and wandered out again without doing anything.
I just gave the waiter a hard stare and he dropped his head before I ignored the bill and paid the regular price for the drinks. As we were leaving, I could hear the overheated tourist still shouting and demanding justice.
Heading Home
After all the mishaps, our return home went smooth as glass. We had an overnight layover in Cancun and then flew to Miami for a connecting flight to D.C. I was nervous about returning through U.S. customs in Miami because I had Cuban contraband stuffed in our luggage. I could claim the Che Guevara T-shirts and a few souvenirs came from Mexico, but the color print of a Cuban street scene and the Granma newspaper would be tougher to explain.
“Let me do the talking,” I told my wife who just shrugged and said I was being paranoid. She was right. The passport officer quickly riffled through our passports before sending us to customs where our bags weren’t searched. Most smugglers don’t bring a baby along for the ride so we looked harmless.
It was good to be home. I doubt Soren will remember our adventures in Cuba. He slept through most of it. 
Images courtesy Brendan L. Smith
Brendan Smith is an award-winning freelance journalist who writes for newspapers, magazines, and websites across the country. He lives in Washington, D.C., with his wife and nine-month-old son. Brendan also is a mixed-media artist who shows work in exhibitions in the D.C. area. More of his articles and columns are available at www.brendanlsmith.com.