Beyond the Embargo: Sneaking into Cuba 10 Years Before Obama Did

This story is non-fiction and these photos are all my own.

10 years ago I snuck into Cuba. I’m an American, and this violated our embargo with them. Spending money on the island meant risking 10 years in prison and a fine up to $250,000. I had just finished my Freshman year studying Political Science at the University of Washington and my mother has always loved Salsa music. This seemed liked reason enough to risk it.

Armed with my three years of high-school Spanish and the beats of Buena Vista Social club, we drove to San Diego, parked her Passat wagon, took a bus to Tijuana and found the man with the bright fanny pack. I don’t entirely recall how we knew “he was the man” but something about his perfectly oiled jerry curls gave us confidence. We paid him $500 cash in exchange for handwritten, paper tickets that somehow got us through Mexican security.

If you’re thinking we’re crazy, we weren’t alone. Travelocity was fined back in 2007 for illegally booking nearly 1,500 flights between the US and Cuba. Various organizations say 20,000–50,000 American’s have snuck into Cuba each year, some even estimate up to 100,000. Many of them, like us, stayed in Casa Particulars, private rooms in people’s homes. The only thing that had been privatized in Cuba besides taxis back then.

Briefly stoping in Monterrey, Mexico before touching down in treasonous territory, I remember my mother and I both nervously reassuring each other that we would be fine, that if friends of ours had done it, it couldn’t be that hard. Still, as I slipped a blank piece of paper in my American passport and shakily slide it across to the Cuban customs agent, I was breathless. When she momentarily glared at me emotionless, and simultaneously stamped the feeble green slip, I exhaled criminal relief. We were in. All was going as we’d expected it would, including our cabby attempting to drive off without starting the meter. My adrenaline fueled spanglish took care of that real quick.

The week that followed was much of what you’d expect and a lot that you wouldn’t. The realities of communism are fierce. Armed police are on every corner, semi-automatic weapons slung like the man-bags of American metropolis. The food is rationed, so grocery stores don’t exist. If you’re staying in a Casa Particular, you’re eating the food of the family, and drinking their intestinally-risky water. If you’re staying at a resort (all of which are owned by the government) you’re eating the food the Cuban government wants you to think cubans eat. We seek the most authentic experiences in reason when traveling and stuck with the former. Our bellies suffered, but our minds expanded.

I did not see or eat a cuban sandwich while I was there. Cuban cigars however, live up to the hype. Once you have had a freshly rolled Cubano… patiently let the moist Caribbean tobacco smoke to rest upon your tongue and allowed the dew of resin to numb your lower lip, you’re never quite the same. Pair with the exquisite no-mixer-needed Cuban rum and a view of the sea hanging over the Malecon and you’ve got utopia. That said, living on ~500 calories a day while sleeping on 40-year-old mattresses (read: springs) was exhausting. The rum and cigars are essential to keeping you giddy.

Cuba is a country preserved in time. Extravagant tropical luxury left behind by nations battling for hegemony. Classic cars do cruise the streets lined with rusting wrought-iron. Colors burst from every corner despite the dilapidation. The bright teeth of the smiling children lift the spirits of yesteryear’s memory. It was easy to see why it has been a place of inspiration, and a place of conflict for decades.

Cuban officials rapidly became keen to our presence and decided to “visit” our Casa Particular and “ask a few questions.” If you’ve ever been interrogated and outnumbered by armed officials in a foreign country, you know it’s rather… sobering. Thankfully, because I was a student and my mother is a doctor, we were able to frame our visit as an opportunity to see two things Cuba does best: medicine and education. Both are free and good there. We were not. We ditched the police (who trailed us after we left the residence), headed to Cienfuegos and beached two final nights, before we jumped on the next mystery-midnight-express flight back to Mexico.

The US Border Agent in Tijuana asked me only one question crossing the border back into the United States. Despite the tightly wrapped smuggled Cubans in my undies and the journal full of memories, there were few traces of our time there. Still, incarceration as a teenager wasn’t exactly high on my list of resume boosters.

“Who was the 16th President of the United States?” He asked, looking at my Passport and California Drivers License.

“Abraham Lincoln, sir.” I said, without hesitation.

“Welcome home,” He said, visibly shocked.

Finally, proof my liberal arts education was good for something.