How I Traveled to Cuba Illegally

Josh Plotkin

As Americans, we often think of ourselves as the “land of the free.” Indeed, we have many freedoms that other countries can only dream about, such as the right to openly protest against the government; the right to practice any religion you want; and the right to bear arms. But there is one freedom that has been conspicuously denied to Americans for almost 50 years: the freedom to travel to Cuba.

During the Cold War, Cuba’s close ties to the Soviet Union worried President John F. Kennedy. In the aftermath of the Cuban Missile Crisis, the Treasury Department passed the Cuban Asset Control Regulations and the Trading with the Enemy Act, which froze Cuban assets in the US and made it illegal for Americans to travel to Cuba. The travel ban lapsed in 1977 under the Carter Administration but was re-instituted by Ronald Reagan in 1982. In 2004 the regulations were changed so that it’s not technically illegal to travel to Cuba, but it is illegal to spend money there.

I wanted to see a Communist country first hand, and knowing that Cuba was off limits made it the natural choice for me. The travel restrictions meant that I couldn’t get there via direct flight from the US, so I first had to go through a country that permitted travel to Cuba (every country but the US). Since I happened to be near Cancun, Mexico, I booked a flight with Cubana Airlines on Nov 2, 2010 (election day). The one flight a day from Cancun to La Habana was aboard a decommissioned Russian military plane that had military grade (read: uncomfortable) accommodations and warning labels in Russian.

Once I stepped off the plane in La Habana, I knew I was in a Communist country. The airport was in an embarrassing state of disrepair that you wouldn’t expect from a country’s main airport; it looked like part of it had caved in and there was a big pile of debris sitting right where I walked into the terminal. When I got to Immigration an agent was there randomly choosing people to harass, and decided I was in need of an interrogation.

“Where are you from?”
“Los Estados Unidos.”
“What are you doing here?!”

He was intimidating and made me feel very unwelcome in his country. After nervously answering his questions, he allowed me to pass, and I continued on to the immigration booth. Because Cuba doesn’t want its revenue stream to dry up, they don’t stamp passports at the airport–American or otherwise–and I didn’t have any trouble when I went back to the US.

In a country where there is some semblance of private property and free exchange, your vision will be filled with people trying to sell you goods and services from the comfort of their clean, well maintained shops with proudly displayed advertisements. Driving from the airport to my Casa Particular in La Habana Vieja, I kept waiting to see signs of commercialization. I saw a few shops there and they were all very small; only a few had signs outside advertising what they were selling, and the signs that were present were small, dirty and beaten up. The city is filled with dull-colors and faded out buildings. Paints and colorful signs are something that are used by businesses who want to attract customers and stand out, but since everything is owned by the state, there is no incentive for anyone to stand out.

One of the few entrepreneurial ventures that the Cuban government allows its citizens to engage in is the operation of a Casa Particular. A Casa Particular is basically a bed that you rent in someone’s house for 20-40 CUC (22-44 USD) a night. In order to run a Casa Particular, Cubans have to be approved by the government and they have to pay 200 CUC (220 USD) a month in order to keep their license, and they are limited to renting out 2 bedrooms. At 20 CUC a night, a family would have to have guests staying at their house 10 nights per month in order to break even.

After checking in, I left the Casa Particular to go explore the city. I walked about half a block before a man smoking a cigar asked me where I was from. At first I didn’t respond because he was walking in front of me, and I wasn’t sure if he was talking to me. In free countries, people generally look at you when they’re talking to you, but in Cuba it’s illegal for Cubans to talk to foreigners. Not realizing this, I caught up with him and tried to talk to him face to face. When I got closer to him we walked faster so that he wouldn’t be seen talking to me directly. As we walked with 10 feet of distance between us, he again asked me where I was from. Then he tried to sell me cigars, and he walked off when I told him I wasn’t interested.

Nighttime in Cuba was eerie and I never got used to the experience. There are no streetlamps, bright signs, illuminated shops, or other sources of artificial lighting; not even the main tourist area with the big hotels had any lighting. However, the darkness doesn’t slow anybody down and the city is very lively and loud. It’s amazing how loud it is since all of the noise comes from people talking. The characteristic sound of cars whizzing by in the US is replaced by the sound of children playing games, people yelling at each other, and televisions on full volume. Walking down a pitch-black street, not seeing anybody but hearing a hundred people gave me the feeling of voices in my head having a dozen conversations with each other.

It was interesting that whenever I had a conversation with someone and I told them that I was from California every one of them replied, “Oh California, the old state of Mexico?” The fact that 4 people had this as the first thing to say about California suggests that this was taught to them in their “free”, government-run schools.

Cuba is one of the strangest places in the world to visit, ranking alongside North Korea. The government uses policies to control its people, and attempts to create the “socialist” man. This socialist ideal, from what I experienced, creates an environment where the people are scared of their government; where individuals lie to your face, pretending to be your friend, in order to scam any amount of money from you;; and those who must become either a pimp, prostitute, or bootlegger in order to make enough money to support their family.

All over Cuba there are signs loudly denouncing the US Embargo, saying things like, “Every 8 hours of the Embargo equals the materials to repair 40 day-care centers,” and, “3 days of the Embargo equals the printing of all the textbooks for one school year.” This is one point where the Cuban government is correct; the actions taken by the US government against Cuba have done nothing to bring about a change in government, and the only people that are hurt by the Embargo are the Cuban people. If the Cuban Embargo were ended, the Cuban government would lose its stronghold on the people; they wouldn’t have a strong case uniting its people behind anti-American rheteric. If the Embargo were ended then Cuba would be opened up to a new market of tourists whose dollars would help increase the quality of life of the average Cuban. Eventually, the Castro regime would collapse under its own weight and there would be a chance for a new democratic government in Cuba.

The status quo is not acceptable. For the sake of the Cuban people, we need to end the Cuban Embargo NOW!

Josh is a guest contributor to the California Review and a world traveler. He is currently in Columbia promoting the cause of liberty. You can keep up with his current travels at:


  1. Hi Josh,
    Interesting article! It sounds like an amazing adventure.


  2. funny .. i loved Cuba the people were amazing. Not just with me but with each other. in a way Cuba is like a prison to them but think of it as being in this prison with all of your best friends its not as bad as you think. they have most of what they need to live. they have each other and help their neighbors without hesitation. with americans they see america as a dream.. they believe the dream is real. What they do not know is not every american is living like a movie star. I could easily live in Cuba… sure the Gov does not goofy stuff but look at what the US Gov. does… We have some pretty nutty people who get elected. The food was great .. lobster for 8 dollars. once you get into the flow with the locals you can grab a cab for a dollar. lunch for a dollar. A night Cuba is safe. people will talk to you that is not a problem the problem is young girls. If your walking at night with a 20 year old girl near the tourist areas the police may believe she is a hooker. if she is stopped twice for working in this way she could get a year in jail. Cubans do not view it as bad.. most view prostitution as necessary its something you do for money and for many there is no other way to get a few dollars.
    i spoke to one of the girls she was a very nice girl and we became friends in a way. She told me her story and why. it was typical. She did not do well in school got in trouble had a kid young. Her father was in jail and her mom could not work. She had a kid. so her plan was she looked for a nice looking tourist guy she would go out with him drinks , dancing whatever and at the end up the night she expected a present. The present was of course money. I know its hard for people to sometimes understand this but even women who choose to do this are people to. They want to be treated with respect and want people to understand why they are doing what they do. I like the girl and enjoyed talking to her. it was a slow tourist time when i was there so she did not have anything else to do. most evenings we were the only two at the bar. I bought her a beer or two many a pack of cigarettes and she was happy to sit and talk with me. One evening i arrived at the bar early, She came up to me and said how are you getting home tonight dont walk you need to take a taxi there are a few guys waiting to rob you. They say you take to much money out of your pocket. When i left i saw the guys trying to follow me. The girl was standing on the corner watching me walk away. She knew something was up. I turned back and said ok your right I ll take a cab. I do not speak spanish so she flagged down a cab and told him where to take me. She never asked for money !!!! she did ask every night if I wanted to go out with her of course but she was very polite. Nothing crude or rude.
    I loved my stay there and cannot wait to return. i made several friends that i guess will likely remain friends for life. Cuba is full of good people they are waiting for life to change I am not certain all of them will like the change but it has to change.

  3. Hi there! I know this is kinda off topic but I was wondering if you knew where I
    could locate a captcha plugin for my comment form? I’m using the same blog platform as yours and I’m having trouble finding one?
    Thanks a lot!

  4. Great article. I’m thinking of going end of April through the DR. I did have one very important question though….When you flew back into Mex did they stamp your passport? If not did you have to ask them not to?
    I hope to hear back from you.


  5. It’s going to be finish of mine day, except before
    finish I am reading this wonderful article to increase my know-how.

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