How I Got Stranded in Cuba During a Forbidden Visit

I wanted to get lost. I just didn’t know how lost that would be.

Sneaking In

Though Havana, Cuba, is forbidden, I am determined to pay it a visit.

It's the day before Thanksgiving in 2012, and I am about to sneak into Cuba.

President Obama has just been re-elected, but thawed relations between the U.S. and the tiny communist island are still years away. There aren't flights on any U.S. airlines between the countries, so along with two friends — Sal and Rodrigo — I take a Cubana Airlines flight from Mexico City to Havana. We're able to buy tickets in the U.S. through a Cayman Islands travel agency that conveniently hides the nature of the purchase when charging our credit cards.

Still, with passports and boarding tickets in hand, there is plenty of anxiety and anticipation. This is the forbidden land, after all.

Forbidden Fruit

A man sits on a bike beside a mural of Ernesto Che Guevara, a key figure of the Cuban Revolution.

Cuba is many things to many people. For me, visiting is as much about rebellion as anything else, although not in the revolutionary kind of way. I never owned a Che T-shirt in high school, but I still don’t understand why communism is so scary. Before leaving, I read breathless accounts of the wonders of traveling in Cuba as a foreigner, particularly an American. “It won’t be like anything else you’ve experienced," I'm informed.

At the time I have just two stamps in my passport, so I am eager to experience the unknown, to get lost.

I just don't know how lost that will be.

Entering Cuba

Taxis are all cars from the 1950s, like this Ford.

After landing, we find that Havana's José Martí International Airport is literally full of soldiers. We are repeatedly told that it’s all for the protection of economy-fueling tourists like ourselves...but that doesn't make it any less unsettling.

Once the U.S. passports come out, all three of us immediately attract attention from the authorities. After being pulled from line, our suitcases and wallets are meticulously examined while we are all individually pulled aside; we are let go only after being questioned at length, Rodrigo for more than an hour.

After leaving the airport, we take a ride from a cab driver who tells us Obama will save Cuba. We then check in to our very budget-friendly “casa particular,” located inside someone’s home and costing us each $15 a night with a $7 daily breakfast. Most of the foreigners we meet are staying in one of these accommodations, although some opt for the expensive old hotels.

Vamos Amigos

One thing that quickly becomes apparent when we get into the city is that Cuba is nothing like where you’re from, no matter where that is. There is no advertising anywhere, save for the socialist propaganda. There are no supermarkets and department stores. There are no smart phones or Wi-Fi in public places (as far as we can tell, only a few swanky hotels have Wi-Fi access). The taxis are from the 1950s, somehow kept alive with Russian auto parts. They spew a black smoke as thick as a Guinness. Things are either crumbling or in pristine condition. The roads are a mess of potholes and stones with little to no signage.

Through it all, Cubans are some of the warmest and most inviting people you might ever meet.

Food and Drink

We have just three nights to spend in Havana, and we want to make the most of it. Sleep can be had some other time.

We hit up all the famous tourist bars where Hemingway drank — specifically, Floridita, known as the home of the daiquiri, and La Bodeguita del Medio, the birthplace of the mojito — and all the clubs that have music blaring out onto the street (which is essentially all of them). Instead of restaurants, we eat in paladars; similar to our accommodations, these are homes that have been partially converted into places to dine. It's here where we eat real Cuban food, which generally means chicken, beans and rice, possibly with a small salad of some sort.

We find all the cigar factories that are open, and spend most of our money at these places just drinking rum and smoking cigars while mingling with anyone who comes in. We meet dozens of tourists at these places — including a guy named Gary who reappears late in my trip.

'Nothing Will Happen'

Havana Airport — José Martí International Airport, where I will learn a startling truth.

After three whirlwind nights in the city, I’ve spent every dollar I brought, and I still have to make it home.

Luckily my friends have extra cash, so I borrow $50 from Rodrigo to pay the $25 tourist tax at the airport and the $25 cab fare to get there. I also leave later than them because we have different flights back to Mexico City and I believe mine leaves later.

Rodrigo insists on giving me all the money he has left “just in case something happens.” I refuse to take it, insisting nothing will happen.

Famous last words.

Penniless and Alone

Tickets — At the airport, a numbers mix-up sends my trip into a tailspin.

Perhaps it was all the drinking and lack of sleep, but I neglect to realize that the flight time on my ticket is in fact 5:00 hours and not 5 p.m. So when I arrive at the airport, there is no one at the Cubana check-in counter. When I finally find someone who can help, he tells me there were will be no more flights that day. The next flight he can put me on is next Friday — and I’ll need to pay a $100 rebooking fee.

It's Saturday, and I have $25.

Panic Sets In

Streets of Havana — The streets of Havana, which I realize may soon become my home.

I have plenty of money in my bank account, and a few credit cards. But because of the embargo, I can't use those things in Cuba. I knew this, and yet I didn’t take Rodrigo’s money and I didn’t bring enough of my own. I am, in a word, screwed.

At each airline the story is the same: Without a valid credit card, there’s nothing we can do to help you. I ask other people checking in if they can lend me money, telling them I will pay them upon landing, wherever that may be. I am willing to go anywhere just to get out of here. Most of them don't understand me or don't care. One airline employee tells me to stand at the customs exit and wait for a generous American to come out.

The horror sets in. I am stuck in Cuba with no money and no friends. I will end up like Alan Gross, who was everywhere in the news at the time, an American imprisoned abroad for years. I will slowly waste away in a Cuban jail while my mother desperately pleads with the State Department to rescue me. They will tell her there’s nothing they can do, and I will die in Cuba.

Time to Think

The historic Saratoga hotel, possibly my saving grace.

I pace the airport exploring my options, of which there are few. I think about all the people we met, but I didn’t get to know any of them well enough to find out where they were staying. Except one guy.

During our trip to a cigar factory, we’d met Gary, an extremely jovial Brit traveling alone. He wore comically English outfits, like something you might see on “Masterpiece Theatre.” He had a monocle and a walking stick, which he actually needed because of an accident. Gary had taken a liking to my friend Sal, and I actually remembered a conversation they’d had about the hotel where Gary was staying. He had said it was one of the nicer hotels in town and that we should meet him there for drinks, which we did not do.

But I remembered the name of the hotel: the Saratoga.

Returning to Havana

Havana Taxi — On the taxi ride to the hotel, I'm in no mood to chat.

The $25 I have to my name is enough to take a cab back to the city. The cab driver, who speaks English, notices that I'm wearing a T-shirt commemorating the recent San Francisco Giants’ World Series victory. He, like many of his countrymen, is a huge baseball fan. I, however, am a panicking mess of a human being and can not possibly engage in a conversation with him. I don't want to explain my horror story of stupidity, so I pretend that I’ve been to Cuba before and don’t talk much for the rest of the ride.

Upon entering the Saratoga hotel I realize that I don't know Gary’s last name. So I describe him in detail to the receptionist. She looks perplexed and says she can't help me, but that I am welcome to wait in the lobby and maybe he’ll pass through. So I find a seat next to the elevators and wait. After 30 minutes I start to doze off. Then I hear his voice.

Gary’s unmistakable accent echoes through the cavernous lobby and lifts me out of slumber. He's talking to a hotel employee as I run toward him screaming his name. He looks at me and says, You’re not supposed to be here.

Hatching the Plan

Saratoga Roof — View from the roof of the Saratoga, where a plan is set in motion.

Gary takes me up to his room and I explain everything. He says he’d love to help but that he might not be able to do much. You see, Gary has himself run low on cash and there is no way for him to withdraw money until Monday (at this point it's Saturday evening) because he has to physically appear at a bank to do so. And he’d run into a problem using his credit card because, he suspected, the bank was partly owned by Americans and thus barred from doing business in Cuba.

The bottom line: He doesn't have enough cash to loan me to buy a new plane ticket, get a cab back to the airport and pay the tourist tax that’s required for departure. Plus I’d probably need some food and water in the ensuing time it would take to make all of this happen. But as my relief quickly turns to further panic, Gary reveals the wild card: Wi-Fi access.

The Saratoga is a gorgeous, palatial building in the center of Havana, just off the old town. And in 2012, it was one of the only places in the city with reliable Wi-Fi. Sure enough, when I turn on my otherwise useless iPhone, it detects a signal. This is huge, because I can use my credit card with a Mexican airline. In a matter of minutes I have a flight the next day, Sunday, at 15:45 hours (won’t make that mistake again!). And just like that, for all the hemming and hawing, I am going to make it off the island after all.

One Last Hurdle

Saratoga Lobby — The lobby of the Saratoga, where I will be thwarted in my attempt at a comfortable stay.

Gary is kind enough to take me out for dinner, and he also gives me the money I need to get to the airport and pay the tourist tax. He also says I can try — try being the key word— to stay in his room for the night, but that the hotel has a militant policy on additional guests. That proves to be abundantly true when I try to sneak in and find a manager stationed in the lobby, checking people's IDs as they arrive.

Gary and I try to walk up the stairs to avoid him, but he tracks us down. I tell him I'm Gary's "friend" just coming by to hang out; he immediately looks suspicious and says that isn't allowed. But my luggage is up in the room, I reply. Can I at least get that?

After reluctantly agreeing to let me up, he sends someone to check on me about three minutes later, then has someone else start calling the room repeatedly until I come downstairs and leave the hotel.

That night, in lieu of a comfortable hotel bed, I attempt to sleep while slouched over my luggage at the airport, interrupted by the sounds of the cleaning crew. The attempt is not successful.

Lessons Learned

Havana Skyline — I won't forget the beauty of Havana — or the kindness of strangers.

The next day, when I finally get my plane ticket and go through customs, I know I’ve weaseled out of certain doom thanks entirely to the kindness of a stranger. I insist to Gary that I pay him back, but he says if I really feel strongly about it, then I should donate the money to a good cause.

For all the travel 101 lessons I so callously discarded during the journey, I come to learn the greatest lesson of all — that the human spirit is inherently good, and we all first and foremost seek to help those in need.

It's a lesson I won't soon forget.