Cuba trip

My Cuba Trip 10 Years Ago: How I got into trouble

Cuba trip

Now that relations with Cuba have improved, is it okay to admit that I’ve been there? Back when it was illegal for Americans to go?

I grew up in Bulgaria during Communism when travel outside of the country was severely restricted. Cuba was one of the few places I could visit. But I wasn’t interested in Cuba. Why would I want to go to another Communist country, one that was even more impoverished than my own?

After the fall of Communism, I immigrated to America and made my home in New York. Ten years later, I was desperate to visit Cuba. Cuba was now interesting to me. It was exotic, mysterious and, best of all, forbidden.

Cuba trip
My best friend and I didn’t deliberate long before we decided to go. But we had to be careful. We had both recently become American citizens and didn’t want to jeopardize our status. We’d heard rumors that Mexican and Canadian airlines flying to Cuba gave out their passenger lists to the American government, so we opted to go through the Bahamas. We would use our old-country passports instead of our US ones. We had both recently gotten married and taken our respective spouses names but in our old passports we were still listed with our maiden names. Perfect. There was no way we’d get caught.

Or was there?

Cuba trip

As planned, we flew to the Bahamas on our American passports pretending to be on a weeklong beach vacation. But instead of getting a taxi to one of the resorts, we turned around and jumped on a flight to Havana.

Everything was fine and dandy, until it was time to leave.

At the airport in Havana, we passed through security and joined the line at immigration. My turn came and I walked up to the immigration officer—a handsome guy with a mustache. “Hola! Cómo estás?” I said with a smile. It was all the Spanish I knew but I’d proudly used it all week. I handed him my Bulgarian passport. The same passport I’d used to enter the country. He looked at my photo then back at me, nodding slightly with a smirk under his mustache. He said something about búlgara chica. On the streets of Havana, I’d suffered endless catcalls and outright propositions, but it didn’t hurt to be friendly with the immigration officer. So, I smiled and said, “Si, Bulgarian.”
Cuba trip

He nodded again approvingly, then took his eyes off me and leafed through my passport. When he looked up again, his smirk was gone. He asked me a question in Spanish and, from his tone, I could tell something was wrong. I tensed.

“No hablo español,” I said. His eyes narrowed as he studied my face. Finally, he spoke in English. “Where is your visa for the Bahamas?”

I stared at him. As an American, I didn’t need a visa to enter the Bahamas. But he didn’t know that I was an American. He had my Bulgarian passport in his hand and was refusing to let me on the flight without a visa. I had no choice but to tell him that I had another passport.

“American passport?” he said, his eyes turning into slits.

I breathed in and handed it to him. I attempted a smile but his face remained stern in response. He opened my US passport.

“This is a different name,” he said.

Cuba trip
I tried to explain but he turned his back on me and picked up the phone. He’d barely put the receiver down when his supervisor stood in front of me. She was a hard woman in her 50s. Any chance I might have had of charming my way out of this was gone.

She peered at me with cold hazel eyes. I was conscious of the sweat stains forming on my T-shirt.

“Do you speak Spanish?” she asked. I shook my head. “Yes, she does,” the guy said.

Great. He clearly thought I was an American spy who was lying about not speaking Spanish. I motioned to my friend to come over. She at least spoke a little Spanish. She tried to explain but she was in the same boat—two passports (one of which was American!) with two different names. After a short exchange, the supervisor ordered us to follow her. She sat us down on a bench in front of her office and told us to wait. My friend and I looked at each other. “You know what she told me?” my friend asked, indicating the supervisor. “She said she could throw us in jail.”

Cuba tripI swallowed hard. I am one of those people who worry about anything and everything, anticipating problems at all points and junctures. There would be traffic on the way to the airport and I’d miss my flight; my credit card wouldn’t work abroad; I would be late for a job interview. And, of course, during this entire trip, I’d worried that the American government would get wind of my little excursion to Cuba and slap me with a fine. Or that they’d put me on some list and give me a hard time at immigration in the future. But jail? That was a concept that had never entered my universe of worries. And in Cuba, of all places?

The minutes ticked by. My friend and I sat there, staring at our feet. We should have been strategizing, getting our story straight. But we were too scared to talk. And anyway, what options did we have? It was not like we could call the American Embassy and ask for help!

Cuba tripAfter what seemed like two hours (but couldn’t have been more than ten minutes), the supervisor emerged from her office with a bunch of papers and all four of our passports in her hand. Without as much as a glance in our direction, she walked into another office across the hall. Through the open door, we could see her talking to someone as she pointed to the papers. We sat there watching her, trying to read our fate in her gestures. My ears were buzzing. Finally, she left the room and headed our way. We stood and waited. I watched her face closely as she neared, but she betrayed no emotion.

“You made a big mistake,” she said. We nodded. As long as she would let us go, we’d gladly accept the title of the world’s biggest fools.

In the end, we got away with just a long lecture on how we should have used our American passports. But the effect was quite sobering. I had become cocky and arrogant in the ten years I’d lived in the States. I’d felt invincible as an American citizen. I was so busy trying to outsmart the US Government, it never occurred to me that the moment I disregarded the travel restrictions and boarded a flight to Cuba, I was on my own.

I thought I would never care to return to Cuba. But now that the travel restrictions have been lifted, I’m getting the urge to go back, this time as an American.


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