How to Travel To Cuba Illegally(?) From the United States

Ever since Dirty Dancing: Havana Nights, I've been wanting to go to Cuba. That Diego Luna sure can dance!

Okay. That was a blatant lie. He was a mediocre dancer next to Patrick Swayze. It was Scarface. I just HAD to see the country that could produce a fictional character like Tony Montana. And let me just say, I was expecting high-fives walking through the streets yelling out, "say hello to my lil friend!" Nope. Not-a-one. Just a lot of Spanish curse words attached to the word "Chino". So I guess I have mixed feelings after my five night stay.

Well, if you're not Beyonce and Jay-Z, chances are you cannot legally go to Cuba on your own without being on a sanctioned tour of some kind. In doing massive amounts of research, I found out that it's not technically illegal to go to Cuba, but it's illegal to spend money there. Quite the technicality. That would be like going to a strip club and not being able to open your eyes or touch anything. (I'm good at similes involving strip clubs.) I realize that I stand a chance of being fined by the U.S. Government for visiting Cuba and helping you visit the country as well, but if that happens, hopefully I will become a martyr. I'll ask for contributions on Kickstarter and then print out shirts for people that say, "Free The SVB!" And I will use the "martyr" pedestal recklessly as I ask people to buy me drinks and to show me their boobs (men and women).

As a frequent traveler, Cuba has always held a mythical place in my mind. I had imagined I would go there for my bachelor party one day, but being as that is nowhere remotely in the distant future, I decided to surprise myself. In my mind, I thought of beautiful beaches, nightclubs, classic automobiles, and people - unspoiled by fat, obnoxious, unwilling-to-learn-Spanish, smug, culture-ruining American tourists. The fact that it was "illegal" was also intriguing. I never liked the thought of someone telling me I couldn't do something. (The NBA is still in my future, you hear me Pop?!?) I can understand the U.S. preventing us from going somewhere that would endanger our well-being - heck, we can go to places like North Korea, Syria, or Rwanda, although it's not recommended - but Cuba?!? If we should listen to Senator Marco Rubio, then it's about rights not afforded and atrocities committed by the Cuban Government against their own citizens. In that case, there should be dozens of countries on the list of places we are "banned" from visiting.

Anyhow, since I like the sound of my own voice, I'm going to play the reporter and the interviewee subject to help you travel to Cuba as well. Because I did hours of research before booking my flight into Mexico City with plans to fly through to Cuba, I know there are a lot of confused, worried people out in the forums of the world. After the Q&A, I will go into my personal experiences in Cuba - mostly about prostitutes! - if you want to skip the questions altogether.

Kevin, let me ask you... first of all, you're a handsome man. If you're not doing anything after this, we should grab a drink in my hotel room.

If you're paying for the mini-fridge alcohol, I'll be there.

Great. I brought condoms, so we're good. I don't know how I'm going to be able to concentrate through this interview now - I feel like a schoolboy again. Anyhow, IS it illegal to travel to Cuba?

That's a great question - Pulitzer-worthy. From everything I found, it's not illegal to travel to Cuba, but it's illegal to spend any kind of money there. 

Okay, how do you get from the United States (U.S.) to Cuba then?

This part is rather tedious. If you do a search on Kayak, Expedia, Orbitz, or any of the flight-search aggregators, you will not find any results for any destination in Cuba. Therefore, if you're not going on a tour or getting a special Beyonce/Jay-Z license, you will need to fly into Canada or Mexico first. I decided to fly into Mexico City first (that's Ciudad de Mexico for the Spanish-speaking layman), although Cancun is also another place you can fly into in Mexico that flies to Havana (Habana), Cuba. The ticket from Mexico City to Havana is rather cheap. Around $200 to $300, and even cheaper from Cancun. I just had never visited Mexico City before, so I decided to go there. (Loved Mexico City, btw.) 

I bought my ticket the day before in Mexico City for about $75 more from a travel agency. I just stopped in and asked them to buy it for me. I put it on my credit card too, which only lists the expense as one for the travel agency and not anything mentioning Cuba, which is where a lot of Americans are concerned. They don't want to leave a paper trail. I met a couple there while I was traveling who were from Oakland - no, they weren't pimps, nor did they have an emerging maple syrup conglomerate - and they used a Spanish-based website to book their ticket to Havana from Mexico. I had tried to use it while in Mexico, only I didn't have access to a scanner or fax machine. After you book, they send you an email asking for a copy of your credit card (both sides) and your passport and to fax it or email it to them. FedEx Kinko's have apparently not made their way into Mexico City just yet, so I decided to go to the travel agency. But, if I were you, I would go through Rumbo while you're here in the states to save yourself the hassle. The charge will be listed as Rumbo, so once again, no paper trail.

That was the longest, boringest answer I've ever heard in my life. I guess I should've cared more about this story before agreeing to this interview, because all I did while you were talking was think about how incredibly bored I was. Next question. You mentioned that it was illegal to spend money in Cuba or something, I wasn't really paying attention, but how do I get around doing whatever it was that you said I couldn't do?

You'll have to bring cash with you to Cuba to exchange, because any bank card that's connected to any American-operating bank will not work. Not to mention, I don't think I ever saw an ATM machine anywhere around - although I was mostly drunk and asleep during daylight hours. You should either bring Euros, Canadian Dollars, or American Dollars. The problem with American Dollars is that there is a 10% surcharge that Cuba takes from American Dollars, so if you trade in $100, they give you back $90 worth in Cuban Convertible Pesos (CUC - pronounced "cook") which is only for tourists. There's the Cuban Peso that the locals use. Although, if you take the time beforehand to get Euros from your bank, you're not getting a very good exchange rate, so the hassle might not be worth it. The only real worry for me was having so much cash in Mexico, but it's something you'll just have to do. The alternative is going to the ATM at the Mexican airport and withdrawing Mexican Pesos there and exchanging it for American dollars at a huge loss at one of the currency exchangers. 

Okay, how about living, hotels, where to stay in Cuba?

Since I like to live dangerously, I didn't book any living accommodations beforehand. (Things always work out for me, except for that one time when I got kidnapped for several days, gang-raped, and urinated on in Puerto Rico.) I had heard about Casa Paticulares, which are private rooms in people's homes, that you can rent. It's like what Airbnb does, only they don't operate in Cuba - much like most of the internet. You can use this site that I found on the web to book beforehand:, but I didn't do it that way. I hitched a ride from the airport with my two new friends from Oakland (I feel like I got instant street cred for saying that), which cost $40 (one of the most expensive things in Cuba!) into Old Havana. THIS is the area where you want to stay. Once my acquaintances checked into their Casa Particular, the lady of the house was so amazing, she called several friends to see if they had any openings. THEN, she walked with me several blocks to find the house. It cost me $25 a night! You could stay in a hotel for four times the cost, but you learn so much more about the people living in their homes! I had everything I needed - a private room with its own bathroom and air-conditioning!

While you were answering the last question, I was on my Facebook app seeing if any of my female friends have posted any bikini pictures recently. No luck. Also, I did some more research and peeps on the internet are concerned about U.S. Customs Agents seeing that their passport is stamped twice from entry and exit into Mexico.

Yes, I had read about that online as well. Some people would ask the Mexican Customs Agents, or attempt to bribe them, NOT to stamp their passport when re-entering Mexico from Cuba. This seemed to work for some, and not for others. Being as that I was out of money, hungover, and tired, I decided that I didn't care. I let them stamp it without a peep because I didn't want to exert the energy it would've taken to open my rum-flavored mouth. When I got through U.S. Customs, they didn't even ask about the second stamp. I don't know how hard they look, as those stamps aren't exactly clear or in large print. 

Anything else I need to know about traveling to Cuba as an American citizen? Anything crazy happen to you? Like abducted by Aliens? Anal probing? Or anything that would make this interview much more interesting?

Besides almost running out of money, and seriously contemplating asking complete stranger tourists to loan me some with the promise I would "mail them the money once I returned to the States," I did have one issue with customs in Havana when arriving. For some reason, I, and the gal I had met from Oakland, had been singled out for interrogation, or questioning, however you want to look at it. I was not given an explanation, but kept for about an hour. My indignation seemed to only make matters worse. It's a really scary feeling to realize that you have no rights. I then began to realize all the things they tell you about a communist country and how I would probably not be granted any sort of trial or court hearing if I got thrown in jail. In the U.S., you can throw a temper tantrum if they undercook your French Fries - here, the interrogator let it be known, just by the way he looked at me that he held all the cards. I have never felt so powerless, as every answer to his questions did not seem to satisfy him. His look was pure animosity and was one you'd give a convicted criminal, and that's how he made me feel.  Finally, after what seemed like an eternity, he let me go through, where I met up with the other girl who was also questioned. She had heard that it's a random process, because other Americans without licenses - like her friend - did not get stopped. So, I may never know why I was targeted, but it was the only bad experience of my trip. 

Okay, well, I'd say thanks, but I don't feel thankful for having sat through that interview. I really want my time back. Anyhow, I'm going to go up to the hotel room and get the mini-vodkas ready.

I had really high expectations of Cuba. I wanted it to be such a throwback, where the people hadn't been tainted by American tourism and the hustle that goes along with it. Unfortunately that's not the case. Walking around, you can tell that tourism is a significant part of the country's revenue - even minus Americans. Several people would come up to me and ask if I needed a taxi, or wanted to buy some cigars, or find a girl. It got tiring. Even people I thought were just friendly locals I was having a drink with, would eventually try to siphon me off towards someone's living room to buy some cigars or trinkets. It makes sense. Varying stories will tell you that people make anywhere from $20 to $30 a month. I spent three times that every single day. I don't really understand the intricacies of a socialistic communist society, but while they may get some money from the Government, they are also making money in other ways. There were private businesses, and people selling things on the street, the casa particulares, and restaurants amongst other things. It was odd though not to see an extreme amount of capitalism. You don't see billboards for Coca-Cola. You don't see any McDonald's or Starbucks. We live in such a society that advertisements are commonplace no matter where you look or listen, so it was actually kind of refreshing.

There are an estimated 60,000 vintage American cars in Cuba from the 50s and prior, which is just about one of the coolest things to take in as you walk around the streets. All of the buildings also have a very retro look, because, as far as I can tell, nothing has really been built since the 50s. Those buildings are all in a state of extreme disrepair and it's a tragedy. By opening up capitalism, I'm sure we'd see a lot of the buildings repaired, but we'd also see modernization, which would ruin much of the uniqueness. In 2011, the Castro administration made it so that people were finally allowed to buy and trade cars, so you'll see some newer models out on the road. The biggest loss from tourism being opened up to Americans is the money that people would have to buy new cars, rather than repair their old ones.

As it is now, the Cuban people seem to have what they need. When you live in an egregiously consuming society, like ours, you always want more. You want what those advertisements tell you you don't have. I don't want to see that kind of lust happen to pure people. When I would have a drink (common theme for me) with the people I was staying with, we would sit around in rocking chairs just talking and laughing. When they did watch TV, it was on 25 inch TVs from the 90s, and not on ultra-high-def smart panels. They didn't seem one bit concerned. I often saw kids playing baseball or futbol in the streets, as opposed to the States, where most kids are sheltered by their parents (with good reason), bundled up with their latest XBOX games or tablet apps.

While drinks were cheap at the nightclubs - about $3 - many of the girls I met were prostitutes, or possibly "became one" knowing that I had money. I knew it as soon as I'd post up at the bar and would be surrounded by a gaggle of hot women. I tried to give myself the benefit of the doubt, but then when their hands began to run amok on my body, I knew I was not THAT sexy. The woman showing me the most attention was one of the hottest girls I've ever seen. She would not leave me alone or stop eyeing me from afar. Unfortunately, I've never paid for a prostitute and didn't plan on doing it then either. I even told her this, to which she gave me a sound alibi, which is that we would hang out, dance, and have fun that night (she wasn't drinking, so it would've been cheap), then go home together, and if, in the morning, I wanted to "give" her money, I could. After much internal deliberation and personal anguish, I meekly said that I couldn't. Even for a man of such ill repute, I still have some morals.

I spent four nights in Havana, one in Trinidad, and a day trip to Varadero. Sometimes I'm amazed at how ignorant I am. Just like with Puerto Rico, I didn't know there was more than one city to explore. I guess I just assumed there was only Havana. But also, just like with San Juan, Puerto Rico (I visited Vieques and Culebra), I'm extremely glad I went outside of the main city. Four nights is perfect for Havana, one full-day is perfect for Trinidad, and I wish I could've stayed a night or two in Varadero, a touristy beach resort area, but I was running out of money.

Overall, I enjoyed my stay, but don't know how eager I would be to go back. I guess I assumed everyone would be out on the streets dancing Salsa, and the nightlife would be raw and sexy. I feel let down. There were still pockets of Salsa-infused culture, but not close to anything like Dirty Dancing: Havana Nights! My favorite moments were when I was past the "point-of-sale" with people, sitting in the casa particulares with my hosts, getting them drunk, and sharing a laugh in a language I can barely speak, or taking a spur-of-the-moment trip across the country and not being sure whether I would have enough money to make it back. Cuba should be visited. Soon. There's plenty of countries you can visit where you feel transported hundreds of years, just by the architecture and buildings, but there are very few that you can visit where you feel like you're stuck in the 1950s.

It won't always stay that way.

In Superman II, the Christopher Reeve versions, I was always confused as to why Gene Hackman asked for Cuba as a thanks for his services. I get it now. And I hope you all explore it "illegally" for as long as it stays that way.


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