Viva Fidel painted on a wall in Trinidad de Cuba.
“Que es eso?” Asked the humorless customs agent as he held up my toothbrush. The Cuban officials at the airport in Havana had emptied the entire contents of my backpack on a metal table and were going through them item by item, making me explain everything. It was becoming increasingly more difficult to keep a straight face. I wanted to tell him that it was a secret listening device, but one thing I have learned is that people in officialdom are impervious to sarcasm.
That was the year 2003 and I was traveling to Cuba on my own, on a whim. Japanese and European tourists with rolling luggage and giant cameras swinging from their necks went right through immigration. As a solo American, I was getting a more thorough questioning. It was a bit stressful. Had they arrested me, it wasn’t as if I could call my embassy.
After an interrogation that lasted about an hour, the Cuban guard reached across the table, shook my hand and spoke to me in English for the first time. “WELCOME TO MY COUNTRY!” he said with a huge, beaming smile. He was instantly transformed into a friendly man as soon as he deemed that I wasn’t a spy. I walked out of the airport, into Cuba, back in time about 50 years, and right through the American embargo. It turned out to be two of the best weeks of my life.
With the thawing of relations and easing of the embargo by the Obama administration, I think big changes are ahead for Cuba. There will be an influx of American tourists, money, and maybe more freedom for the people of the island nation. This makes me both sad and happy. I’m sad because the amazing country that I visited in 2003 will be transformed so completely once capitalism comes charging in that it won’t be recognizable. There will be mega-hotels, flashy new cars, a wide gap between rich and poor and thousands of sweaty, American tourists waddling about like penguins.
But when change in the form of economic and political freedom comes, overall it will be great for the Cuban people. The Castro regime and Communism are still alive and well, but I think more contact with Americans and more cash into the economy will hasten change. The Castros have held up the embargo as an example of American imperialism and have argued successfully that they are the bulwark between the Cuban people and Yankee domination of the island.
Travels in Cuba
At the time of my trip, it was necessary for foreign tourists to have their first three nights booked in an overpriced state-run hotel. I created a fake email confirmation, something that multiple customs officials closely examined and questioned me on.
As soon as I walked out of airpot after my tense interrogation, a lady said to me, “Do you have a hotel?”
“Si, si, si,” I replied. I’d been lying about it for an hour.
“Do you want to stay at a private home?” she asked.
“SI, SI!”
And just like that I ended up staying with a cranky octogenarian in downtown Havana for $30 per night, vs. the $75 or so for a hotel. Capitalism is difficult to stop.
Classic cars and colonial architecture – quintessential Cuba.
The next three people I met managed to rip me off. Then I met a guy named Damaso, a smart, young black man with perfect English. He offered to take me around to see the city. We went to the Colon Cemetery and walked through a variety of districts. There are police officers on every corner in Havana, and twice during our city tour Damaso was stopped, questioned and forced to show his papers. He cooperated politely, but he couldn’t hide the annoyance and disgust on his face.
That evening we ended up having a few beers in a local restaurant that was supposed to off limits to tourists. I was very tan then and had on some Cuban-esque clothes. Damaso did the ordering, I did the paying, and we both did the drinking. Tourists at the time were required to spend U.S. dollars (ironically the currency of the enemy) while Cubans used pesos that were about as worthless as toilet paper. We were spending Cuban pesos and it was like drinking for free.
Damaso said to me, “Is it true that in America if you have a car accident, they check to see if you have health insurance. If you don’t, they let you die in the street?” I told him that this was a lie. He asked me hundreds of questions about America, and I asked him hundreds about Cuba.
Damaso was articulate, passionate about his country, well educated and he sexually harassed every pretty girl we saw.
“They like it,” he told me. “It makes them feel good about themselves.”
After a day with Damaso we were walking through the Central Park on the way back home and a portly hooker shouted something at us.
“She only costs $2,” he said
“How do you know that?”
“I had her once,” he replied taciturnly.
When change comes, Damaso will be able to walk around freely without being harassed by the police, tourists will be able to go where they please, and girls won’t have to sell their bodies. And if they do, at least they can get more than $2 per trick.
Beach near Trinidad just waiting to be violated by mass tourism.
Trinidad de Cuba
From Havana I went to Trinidad where I stayed a week chilling on the postcard perfect beach and hiking in the nearby mountains. The beach in Trinidad and the quaint colonial town will be the first place to be ruined when capitalism comes. The beach stretches on forever, powder soft and gleaming white. It leads to clear water that is bathtub warm. It is pure, quintessential Caribbean. There was one hotel on it. There will be 30 big ones in the future.
In Trinidad a girl proposed to me, well sort of. She gave me her address, said we should write each other and get married. I met an Italian girl who had been proposed to by a local man. The Italian girl was – how do I say this politely? – one of the ugliest girls I’ve ever seen. The Cuban man proposed to her because he thought she might be desperate enough to marry him, I assume. Marriage is one of the only ways people can get off the island.
My plan was to go all the way to Santiago and fly back to Havana. In the weeks before my trip, that flight was hijacked two times and flown to the Florida Keys. That would have been an awkward situation if I’d have suddenly arrived in Key West, trip aborted. I’d have been on the news though. “American Man Has Vacation Cut Short,” would be the headline. I bet FOX News would have destroyed me. I can see a smug Bill O’Reilly or self-righteous Sean Hannity mocking me. Jon Stewart would have lampooned me in the opening monologue.
Freedom of travel and emigration will be great for the Cuban people and they won’t have to hijack airplanes, or worse, propose to ugly girls, to get off the island.
At the time, U.S. credit and debit cards did not work in Cuba. I came with $650 cash and had to ration very carefully. The last two days in Havana, I had $6 each day to spend on food and drink. I ate one meal a day – a massive $4 pizza that they served at a tourist place on the Malecon. Locals would walk by and scoff at the American eating an extra large pizza by himself. Once a fat woman and her kid walked by and she asked for a slice. I declined but she said it was for the child – he was hungry. I gave him a slice but she took it and ate it. Puta.
Being able to use credit cards will be nice, but there aren’t many regular places to spend money in Cuba. The island nation is truly communist. There are no signs advertising cars or iPhones or houses or shampoo. Cubans live on a ration of $10 a month but most everything is paid for. They have some of the best hospitals and doctors in the world. They have a great education system, with literacy rates approaching 100%. Of course what they read in the state newspaper is propaganda, but still. They don’t have street crime or organized crime for that matter, because there is a heavy police presence, but still. Cubans say they live without the good and without the bad. It is true. Arguably, they are better off than their neighbors in crime-ridden Haiti, Honduras and Guatemala. But there is no American Dream, no opportunity to succeed and make a better life.
That will change when capitalism comes. There will be rich and poor, there will be more good, more bad, more iPhones and cars and more unemployment and more struggle.
During my visit there were almost no shops or vendors and there were no signs or adverts. That will someday change.
Returning to America after Cuba
I flew back to Guatemala City and then traveled overland through Mexico to El Paso. I was extremely nervous as I went through customs. Cuban immigration doesn’t stamp your passport, so there was no incriminating visa, yet an examination of my passport would show that I flew from Guatemala and returned two weeks later, but didn’t actually go anywhere.
The man at the American border was a chilled out, avuncular man who had the relaxed air of a man days away from retirement. “Where have you been, son?” he inquired nonchalantly.
“Guatemala, Honduras and Mexico,” I replied nervously.
“Why’d you go there?”
“To learn Spanish.”
“Hell, you could have done that here! Welcome home, son.” He returned my passport and I was back in the USA.
Had he known I went to Cuba, I am sure the contents of my bag would have been spread across a large table.
There are no billboards or signs for businesses, but communist propaganda is scattered about.
All over Cuba there are signs of propaganda like this one imploring people to save electricity. Not a bad message, actually.
All the cars are old school American models. It is terribly photogenic and nostalgic, but it has to be a pain in the ass to keep them running.
The grand Colonial architecture in Old Havana is crumbling. The island desperately needs and infusion of cash.
I visited shortly after the invasion of Iraq. Cuban newspapers featured cartoons such as this one.
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Have you been to Cuba?
Is it time to end the embargo?
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Related: Cuba looking to replace Venezuela oil with US Tourists
Planet Bell 
You got almost philosophical there. What about the humor, the snarkiness? Are you changing on us?
I feel like there was plenty of (attempts at) humor and snarkiness. How about my comment that the hookers will be able to earn more than $2? That was classic Jeff, I thought.
True. That was good. And there was plenty of humor. I guess I was shocked at the philosophy bit. Still reeling.
I’m just trying to keep you on your toes.
Wow, quite an adventure! I thought US-Americans weren’t allowed in? 😀
Cuba wants and needs American tourists, but it is illegal for U.S. citizens to go ordinarily.
I hope Cuba can maintain some of its historical charm. I agree letting Americans visit and do business on the island will be a good thing for them, but there is such a thing as too much of a good thing. My dad was stationed there in the late 60’s but wasn’t allowed to leave the base. I have his service plaque from Gitmo – long before Gitmo was a prison.
Interesting that your dad was there in the 60’s. There are just so few unspoiled places on Earth still and this large island only 90 miles from the worlds richest country is one of them!
We traveled to Cuba about 20 years ago but it really was a plop on the beach and don’t move vacation. Now i would love to go back and experience a more authentic Cuba
It is a really special place and as a Canadian you have no issues getting there, except that you have to fly Cubana Air which is an adventure in itself.
This sounds like it was a special trip, and the good thing was that you were with locals; that’s the only way, really, to see and learn about a place. Will you go back?
Angeline,
I’d like to go back soon! I want to see it in the next year, then a few years after it opens up completely, whenever that may be. I did spent lots and lots of time with locals. I could devote many posts to that. All the young people are so eager for change, and they were also eager to talk to an American. Thanks for commenting.
Lovely and thoughtful article. Cuba is one of my favourite places and earth, and while I’m happy that relations are thawing, so that the amazing Cuban people can enjoy a better quality of life, I’m hoping that the changes coming don’t destroy their amazing culture. As a Canadian, I’ve always been able to visit (and very cheaply), so I admit that I’m a bit worried about the impact of so many American tourists on the country.
It will be interesting to see what happens. Question: I assume you fly there using Cubana and go from Canada? How was the plane? The plane I was on was Russian made and dated back to probably the 60’s or 70’s. It was terrifying.
Actually, no in Canada we get all-inclusive tour packages to Cuba that include flight, all-inclusive resort (food, alcohol, activities etc…) and usually the planes are pretty good. The last one I went on served us champagne in our seats en-route. You can even get last minute deals for as low as $600, for a 3.5 or 4 star resort. 🙂
But wowww, that sounds horrifying. I flew in Soviet Russia in the 80s, and it sounds very similar. I have vivid memories of the seat backs of the plane flopping back and forth as the plane moved. Thank god I survived to travel another day!! 😉
My family worries about terrorists or me being mugged, but what they should worry about are the modes of transport I take. I am glad that you got the Soviet experience with flapping seats.
We were definitely not served champagne en route to Cuba. In fact, I don’t think anyone on the plane had flown before. They all screamed at take off and applauded when we landed.
You should get an award for keeping a straight face with all those ridiculous questions. That seems like it’s straight out of the movies. Interesting post.
Yes, it really was. I had a series of handwritten notes someone gave me on places to eat and things to do. They were all in English and when they found those they thought they had me. I think 3 different people took a look at them. It was scary but very funny at the same time.
Whoa, those are some pretty interesting questions – the drastic change of attitude was interesting, too!
They’re quite different from the questions non-USAmericans are asked when entering the country, but these are also pretty funny (especially the “Have you ever participated in persecutions directed by the Nazi government of Germany; or have you ever participated in genocide?”), and I’ve found that most USAmericans aren’t aware of what tourists have to answer when coming to the U.S. (point 38, a bit further down):
https://evisaforms.state.gov/ds156.asp
WOW! Thanks for sharing this. Yes, we do make it difficult to get into the US and we often take that for granted. It is so easy for us to go into other countries. For me going into Cuba, had I been a little older and arrived with a wife or friends I am sure I’d have walked right in. I was 24 at the time, traveling solo and with a backpack. They want rich tourists; they don’t want people like me who only spent $650 in two weeks and talked to lots of locals.
To be fair, once you answer all those questions correctly (which isn’t that hard), it’s not so difficult getting into the US. At least not if you’re a white European – my Arab partner got some more questions though (but his accent is American and he looks more like a hippie than an Arab, so it wasn’t too bad :D).
The questions are mostly weird and confusing – especially the first time I flew to the U.S., by myself, as a 20-year-old.
It would be interesting to take a look at the border crossing formalities around the world. Getting into China and India was easy, after we went through the giant pain in the butt to get visas in advance. I think Israel and Cuba were the only two countries where I got a lot of questions at the border.
Puta. Hahaha!
I’m glad you liked that…
Wow, that was a bitter-sweet post. It’s nice to get some slightly conflicting feelings while looking at a blog post sometimes (instead of pure feelings of beauty, anger or amazement). I might not agree that economic “freedom” will be great for Cuba, but then again I haven’t been there; and what people seem to mean when they talk about economic freedom seems to be freedom to lobby and freedom to have so much money that you can impact a country’s policies, but then again I don’t know what you mean by it. 🙂
Seems like a very interesting place to visit, as I’ve heard from others as well. I should move fast if I want to see this side of Cuba, I guess!
Yes Hannele, you need to go now! It will be changing in the near future. When I say economic freedom, I mean it more for the lower and middle class. It is poor but needlessly so. For example, baseball is huge in Cuba and I saw kids using sticks for bats and bottle caps for balls or a wadded up ball of tape for a ball. That probably explains why so many are successful in the major leagues. There is very little car ownership, the buildings are falling down, people don’t have money to enjoy simple pleasure. But again, they have excellent health care, safety and education so there is good and bad with it all. Thanks for reading – I know it was a long post.
I will be heading that way in the next couple of months. As you say, hoping to get in early before things change, really want to see the old world as you talk about it here!
Enjoy your trip! It is one of the most unique places on the globe.
I just got back from Cuba and blogged about it, but was too nervous to admit that I also sweated it at US customs. It was just made legal days before my trip, but it still felt wrong to declare it on my entry form. Great recap of Cuban adventures! I only made it to Vinales and Havana, but want to go back for more! Such a photogenic country!
I totally agree. I plan to return this December after a 12 year absence and I’m interested to see how it has changed, or hasn’t. Thanks for reading!
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