I’m an Expert Traveler, But I Accidentally Broke This One Rule — And Almost Went to Jail (Don’t Let It Happen to You)

I know what I'm doing, but I just made a very serious mistake that you can learn from.

After visiting 45 states and 38 countries, I thought I had this whole trip-planning thing down. Turns out, I missed a key law that almost landed me in a foreign jail.

When I booked my flight to Cuba in May, the U.S. was still supporting President Obama’s newly relaxed travel policy, and many Americans were excited to finally be allowed to visit the colorful Caribbean country legally. I purchased a round trip flight directly to Cuba from Los Angeles and was ready to soak in the colonial architecture, fresh ceviche, and jazz music in historic Havana.

Then, about a month after I bought my tickets, President Trump announced he would be re-instituting travel restrictions to Cuba. What did this mean for my trip?  As far as I could learn I was still allowed to visit for the time being, but may be barred from doing so soon. I decided I was lucky to have planned this trip during this unique window of time where Americans are legally allowed to go, so I would not to cancel my trip, but would proceed with extra caution in planning it.

I knew that Cuban travel infrastructure was developing, and there were several hurdles for Americans to consider, the most important being how to pay for everything. American credit and debit cards do not work in Cuba, so U.S. travelers need to bring enough cash for their entire visit. I did my research online, talked to other Americans who had visited, and even went into my bank in person. I learned that Cuba has two currencies: the Cuban peso, which is used by locals, and the Cuban Convertible Peso (CUC), which was introduced in 1994 as a currency specifically for tourists to replace the American dollar that was currently in circulation. The CUC trades at about one-to-one on the dollar, but there is a 10 percent fee to change dollars into CUC in Cuba. To avoid that fee, I took out euros from my local bank, which I brought to Cuba and changed into CUC at the airport upon arrival.

I was a little nervous carrying the equivalent of $2,500 cash around Cuba, especially because locals know that Americans are carrying cash. But that turned out to be an unfounded fear; I felt completely safe traveling in Cuba. I never felt threatened, hassled, or scammed in any way, at any time. During the day I locked most of the money in a hotel room safe, just taking what I thought I would need for my adventures.

From a classic car tour of Havana, to a day trip to the Viñales valley, to several taxi rides out to the crisp white beaches of Playa del Este, I felt safe and comfortable in this all-cash economy. I was also glad I had brought a lot more cash than I thought I would need, as it left me never worrying about running out of money.

So when it came time to go back to the airport and head home, I retrieved my last 800 or so CUC from the safe, packed my bag, and headed out early to check in for my flight. I had asked at my local U.S. bank if I should change my money back to dollars or Euro before leaving Cuba, and they said it would be fine if I just brought the Cuban money back, and probably cheaper for me, so that was my plan.

The airport in Havana is slow and online check in isn’t available — which makes sense because there is very little internet access in Cuba — so I gave myself three hours. I’m glad I did, because on arrival I was pulled aside for screening immediately at passport control. My passport was taken from me and I was taken for secondary screening. I wasn’t worried — I had nothing to hide and I appreciated the attention to safety. And I respect every country’s customs procedures.

After my body had been scanned, swabbed, and tested for residue, my bags were completely unpacked and inspected in their entirety. At this point, I was certain I would soon be released into the terminal to shop for duty-free Cuban cigars to bring home as gifts.

But then something happened. An officer was going through my wallet and a look came over her face. She took all of my money out of my wallet and walked away. I stood there confused, and a little bit angry: Where had she gone with my money? Next thing I know, I am being forced into a small room — not a cell, but definitely some sort of secure detainment office. My husband was equally confused.

I speak just the smallest amount of Spanish and none of the officers spoke English. My passport was gone, my luggage was gone, and I couldn’t see my husband. And I hadn't any idea why I was being detained.

In the room, I was surrounded by officers, questioning me in Spanish in very harsh tones, then ignoring me while making phone calls. I heard my name and passport number repeated many times.

After about an hour, an English-speaking officer came in to question me. She wanted to know why I was in Cuba, where I had stayed, what areas I visited at what times. She repeatedly asked me why I was in Cuba, and if I was traveling alone, and I repeatedly told her I was there with my husband to vacation and maybe write a travel story about the lovely country. I started to get the feeling they thought I was doing something illegal — but what?

The officer finally explained to me that I had committed a crime. I was indignant — of course I was not a criminal! I saw my husband poke his head up to the tiny window and mouthed to him to call the embassy, which he indicated he had already done. At this point I realized that this was more than a security screening... I might not be leaving Cuba. I was legitimately scared.

I didn't have my passport, but I did have my phone in my pocket. I managed to send a few texts to a lawyer friend in the U.S. before they told me to turn it off; my friend told me she would call the embassy as well.

After more confusion, officers coming in and out conversing in Spanish in hushed, serious tones, and glaring at me, my crime was revealed to me: I had attempted to leave the country with Cuban Convertible Pesos.

This is illegal in Cuba, and despite all of my pre-trip research... I'd had no idea. There is also a change office right there in the terminal, after the security screening area, so why wasn’t I allowed to change it there? Other travelers were doing so. But I had been singled out, and there was nothing I could do it about it now. I just hoped I wouldn’t end up unable to leave Cuba for my crime.

I’m not sure what the embassy said or did, but right as my flight was boarding, about three hours after my arrival at the airport, I was asked to sign several pieces of paperwork in Spanish, which I did without hesitation even though I had no idea what they said. I was hoping I hadn’t confessed to something I hadn’t done, but was even more hopeful that this would lead to my release. A few minutes after signing the paperwork the Cuban government confiscated all of my money, my passport was handed back to me, and I was guided to the boarding gate for my flight.

I walked out on the tarmac, up the stairs to the plane, and sank into my seat. It wasn’t until we taxied down the runway and took off into the air that I sighed the deepest sigh of relief, so grateful to be headed home. On the plane I shared with other passengers my experience, and no one was aware of this law. Many, including my husband, had hundreds of Cuban Convertible Pesos in their pockets. I wondered how, in all my research, I had missed this important piece of information. 

Turns out, it was a very stupid mistake.

It’s easy to use search engines to find travel blogs, suggested itineraries, and hotel and activity reviews. But the most important thing you can do before leaving for any foreign destination is to read the U.S. State Department’s travel advisories. If I had done that, I would have been clear on this particular law and not opened myself up to potential detention in a foreign jail.

Despite my scary experience, I would still recommend visiting Cuba as an American, before it’s too late. Just remember to change your money before you head home... or you may not get there.

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