I said I wasn't gonna go anywhere. I said I was going to take some down time, but I got too bored.

I got bored, so now I'm going to Cuba.

I've been itching to travel here for too long, and now that America has (almost) normalized relations with this little Latin American jewel, I don't have much time left. Things in Cuba are going to change fast as American tourist dollars begin flowing in. I'm hoping to catch a glimpse of the "old" Cuba, or whatever is left of it, before the age of globalization is fully realized. In America, talking about travel to Cuba can garner some raised eyebrows. Cuba and America haven't gotten along very well in the past 60 years, and that's putting it mildly. Cuba has long been considered a mortal enemy of the U.S., but aside from a few bullet points about the Cuban Missile Crisis and the Bay of Pigs, how much do you ACTUALLY know about the history here? Be honest.

Cuba has a long and complicated history with the U.S. We'll just start from the beginning...

What The Hell Happened Between The U.S. & Cuba?

Ohhhh boy. Where to start?

The Rise of Fidel Castro

The year was 1957. In spite of some routine political turmoil, Cuba was doing pretty well by Latin American standards. The economy had long been one of the most diversified in the region, and the future was (relatively) promising. Of course, this is mostly thanks to the puppet government that America had installed in Cuba after ousting the Spanish. The face of this puppet government was "President" Fulgencio Batista.

Then, in 1958, a revolutionary by the name of Fidel Castro came into power. After a long, violent civil war, his forces prevailed and Batista went into exile. He fled with a few hundred MILLION dollars in his pocket, and Fidel Castro took control of Cuba. You've heard of him, right?

Castro's political career began when he was a young, idealistic, left-leaning, student-activist at the University of Havana. At the time, the Cuban government was friendly with the U.S., and Castro resented their imperialistic influence over his country. It would be more than a decade before he came into power, during which time he would (1) become a prominent political activist, (2) frequently participate in violent protests, (3) eventually be exiled, (4) later return, (5) attempt to start a revolution, (6) see that revolution fail, (7) be imprisoned, (8) flee the country again, (9) meet Che Guavara (another famous figure in all of this), and (10) then (finally) return for his big victory. Those are the cliff notes.

Upon taking office, Fidel Castro invested in the Cuban educational system, as well as the standard of living. He had had some popularity with the Cuban people as a revolutionary, and as the Prime Minister of Cuba, his advocacy for the disadvantaged continued. Cuba's working class mostly liked him! But it wasn't all good... in fact, most of it was bad.

Why People Don't Like Castro

Immediately following the revolution, Castro's government held mass executions of former government officials and set up massive surveillance programs targeting the Cuban public. Dissent was not tolerated and often resulted in extrajudicial executions. In total, Castro's government executed upwards of 10,000 people, and interned many others. Oh, and did I mention that they were known to have harvested the blood of the people they were about to execute in order to sell it on the black market by the pint? Gay rights were also stripped away, as were religious freedoms. However, perhaps the most well-remembered legacy left by Castro was that of nationalization.

In what many (including me) consider to have been nothing more than mass-theft, Castro nationalized an insane amount of personal property. I'm not just talking about land here either. People had their cars taken away. People had their homes taken away. People had their valuables taken away. Everything they had ever worked for. In accordance with Castro's extreme brand of Communism, Cuba's middle and upper classes, quite literally, lost everything.

So they fled.

What else could they do? Speaking out against Castro could have resulted in their deaths, so Cuba's intelligentsia got out in any way they could, even if it meant getting on a make-shift boat and attempting to sail to Florida. Doctors, lawyers, engineers—they all took their families to sea. It is estimated that almost 80,000 people died while trying to make this voyage. However, many others made it to dry land, eventually settling in Miami. Today, Miami's "Little Havana" is a world unto itself, and when Castro finally died in 2015, this neighborhood held a massive celebration. YouTube videos circulated of Cuban-Americans' grandparents dancing with joy at the news of Castro's death. Some of them were pretty hilarious.

In modern-day Cuba, Castro is not well-liked. The 'brain-drain' that occurred when Cuba's intelligentsia fled the country was on-par with the results of the Cambodian genocide. It takes generations for nations to recover from this kind of thing. Today, Cuba is in a state of abject poverty. Ironically, thanks to Castro's investments in education, young Cubans are actually very well-educated—educated enough to dislike Castro. Still, there is an older niche of working class Cubans who are loyal to Castro that balance the scales... but they are (and have been) substantially out-weighed. At least, that's what I gather. I'll find out for myself soon enough.

I will say this: talks with my Cuban-American friends about going Cuba have not been as positive as I had hoped.

Anyway, let's get back to the relationship between Cuba & the U.S.

The Cold War Begins

America was not happy to have had their puppet government ousted, and quickly took up efforts against Castro. Now, don't get me wrong here... Things under Batista were not great—he had to go—but they got a lot worse with Castro. I'd love to tell you that America began plotting against Castro for the sake of the Cuban people... but we all know that wasn't the reason.

The reason was communism. With the Cold War just around the corner, the U.S. was beginning to fund and create resistance movements within Cuba. Meanwhile, Castro retained control of the country with an iron fist. When the Cold War "officially" got underway, Castro's choice was clear: side with the U.S.S.R. The U.S. put economic pressure on Cuba, and Castro responded in kind, by nationalizing pretty much every American asset on Cuban soil. This did not go over well in Washington D.C. An embargo was levied against Cuba, and things continued to escalate.

Assassination Attempts On Castro

At this point, President Eisenhower authorized the C.I.A. to oust Castro and do what they do best: install one of America's patented puppet governments. With a budget of $13 million, they began scheming. What followed was an insane series of failed assassination attempts on par with a satirical 1960s spy movie. Over the years, every president between Eisenhower and Clinton would try (and fail) to assassinate Castro a combined 638 different times! That's right; even Bill Clinton would attempt to kill the Cuban leader during his presidency, 21 times. This ridiculous string of failures has its own Wikipedia page, and even a full-length documentary that came out in 2006.

How exactly did the C.I.A. attempt to assassinate Fidel Castro? This is where it gets funny. They tried to kill him by...

Rigging his cigars with explosives (he smoked a lot of cigars)
Planting poison inside of his cigars (eventually he just quit smoking)
Trying to get him to wear a rigged scuba suit when he went scuba diving (Castro was a scuba enthusiast)
Booby trapping a conch shell at the bottom of the ocean (this was also for when he went scuba diving)
Paying his ex-lover to swap his medicine for poison pills
Training small animals to carry bombs into his residence
The list goes on... for a looooong time

The last documented attempt was as recent as the year 2000, wherein the Clinton Administration attempted plant a bomb at a speech he was giving in Panama. Needless to say, this was a failure. Castro once said "If surviving assassination attempts were an Olympic event, I would win the gold medal."

Cheah. No kidding.

However, in addition to their attempts at murdering Castro, the C.I.A. also spent millions of tax-payer dollar just to fuck with him. They once tried to give him chemicals to make his beard fall out. Another time, they actually attempted to slip him LSD while he was on the radio in the middle of an important speech—like the Cuban State of the Union. The goal was to get him to start tripping balls and say crazy things to the Cuban public. #proudtobeanamerican

The Bay of Pigs

Things didn't seem like they could have deteriorated much further... until the Bay of Pigs happened. Remember that from history class? It was the time when the C.I.A. orchestrated a full-on invasion of Cuba via a proxy militia group (with American supervision) only to have it blow up in their faces. The C.I.A.'s fake uprising was subdued quickly, and the people that they had recruited to actually carry out this uprising were captured. Most of them were executed. The C.I.A. could have stepped in to help them... but they didn't. It would have been an embarrassment, and full admission of culpability.

In the end, a few dozen Americans were killed or remained missing, along with a few THOUSAND Cubans. The C.I.A. got a slap on the wrist, and then got back to their routine assassination attempts.

The Cuban Missile Crises

This got pretty real for a second here, although this conflict has a lot more to do with the U.S.S.R. than it did with Cuba. And, to be honest, I think that the Cuban Missile Crises is actually kind of misunderstood. If you ask me, America had clearly provoked this when they (or, we) installed nuclear missile silos in Turkey and Italy, just spitting distance from the Soviet border. It makes total sense that the Soviet Union would have responded in kind, by installing similar nuclear weapons in a small country neighboring their aggressor. I don't know what we were expecting.

Anyway, the quick version of the Cuban Missile Crises is that the U.S.S.R. set up nuclear missiles in Cuba, and the Kennedy administration went into panic mode. The whole world held its breath for 2 long weeks while Kennedy and Khrushchev tried to stare one another down, sweaty, trembling fingers hovering over "the button." It was scary. People were ready for nuclear war.

Eventually, the two leaders did the reasonable thing, and deescalated.

Both nations removed the missiles in question, and, with a collective sigh of relief, everybody came back up from the nuclear bunkers they had had installed underneath their homes to resume their normal lives.

I actually think Kennedy was a pretty good leader... but these international pissing matches are frustrating.

Cuba v. America Today

The Cuban Missile Crises was the "season finale" of this whole thing... but even after that, the trouble never really went away. We continued our economic sanctions against Cuba, as well as our bi-weekly assassination attempts. And that was our "normal" right up until last year. Other smaller incidents have happened, like the apprehension of 5 Cuban spies in Miami in 1998... but I'm not writing a research paper here. I'm outlining my travel plans.

Castro died at 90 years old, prompting President Obama to meet with Raúl Castro (Fidel's brother, and current leader of Cuba) to bring things back to normal. The meeting was a landmark in U.S.-Cuban relations.

As a side note, during that meeting, the world was gifted with the most awkward photograph in history (on the right). In spite of this, things still seem like they are turning out okay.

Fun fact: some of the peace talks in the "US-Cuban Thaw" were facilitated by the Pope himself, from within the Vatican.

Long story short, the deescalation has been successful and relations between the U.S. and Cuba have officially begun to warm. In August 2016, the first direct flight from America to Cuba touched down and the way had officially been paved for me to get a flight of my own.

Let's do this!

Formulating Travel Plans

Getting to Cuba turned out to be a little bit more difficult than originally anticipated. While pretty much everybody else on the planet has always been able to go to Cuba, for Americans like me, it's not 100% legal to just go there. From a legal standpoint, I'll need to justify my purpose in Cuba according to the latest set of regulations set forth by our lovely government. Currently, they have outlined 12 categories of activities that are acceptable grounds for travel to Cuba, and I'll need to fit myself into one of those categories.

The good news is that these categories are pretty easy to fit into. "Education" and "Support of the Cuban People" are the easiest categories for the average traveler to fit into. The even better news is that I could easily fit myself into the "Journalism" category as well, seeing as I run this website. And the best news of all is that, even though these are technically "laws," it's been pretty well established that nobody from the U.S. government is actually enforcing these laws. That definitely takes the pressure off, but as an exercise, I took a few hours to get my ducks in a row (legally speaking) for my own peace of mind.

This stuff is a little complicated, so you can expect a much longer "how-to" guide on traveling to Cuba as an American in the near future. For now though, let's skip forward to the fun part...

First Stop: Havana

Far and away the largest city in the country, Havana is the capital city of Cuba, and our point of entry. The population of Havana is 2.1 million, making it the most populous city in all of the Caribbean region. However, Havanas' roots are in Spain. Following the expeditions of the conquistadors, Havana became the springboard for Spain's conquest of the Americas. As such, it became a port of extreme wealth and significance. In those days, the harbor was pretty much always populated by Spanish Galleons, filled to the brim with gold, bound for Europe. This garnered a substantial flow of wealth into Havana, which continued pretty much right up until Batista took control of the country hundreds of years later.

Today, people say that Havana is pretty much in ruins. It was a gorgeous old world city whose infrastructure has essentially been left to rot for past the 50 years. This is an interesting backdrop, with profound implications. However, against all odds, the spirit and culture of the Cuban people is legendary, and I'm looking forward to diving in! However, we won't really get around to this until the end of our trip.

We'll be getting on the road for our next destination the morning of our second day in Cuba, and we won't be back here in Havana until the last 4 days of our trip. So we'll get to spend plenty of time here, but it won't be until a bit later. Let's move on to our next stop...

Second Stop: Varadero

Varadero is a famous Cuban beach, just a few hours east of Havana. This will be our second stop. We'll definitely take some time to relax once we get here, but we also plan on taking a taxi 30 minutes inland to Matanzas to explore the city a bit.

Matanzas is the capital city of the province, and something of a Mecca for Cuban poets and artists. One interesting fact about Matanzas is that it basically translates to "mass murder." Indeed, this city was named after (you guessed it!) a mass murder. The story goes that there was a group of Spanish sailors that were crossing a river to fight a group of indigenous people, and in order to do this, they asked some local fishermen for help. The fishermen agreed, but when they reach the middle of the river, they pushed the Spaniards out of the boat. They were all wearing heavy metal armor, so they all sank like stones and drowned. Fast forward a few hundred years, and the capital city of the whole province is named after this incident!

Back in Varadero, I'm interested to see how American tourist dollars are affecting these sorts of popular vacation spots. Of course, the rest of the world has been vacationing here the whole damn time, so maybe there won't be a huge change. We've booked a nice bungalow on the beach half-way between Matanzas and Varadero so we'll be able to do some exploring and drink out of a few coconuts before we head inland to tobacco country.

Third Stop: Pinar deL Río

We had hoped to include at least one major city besides Havana in our trip. With any luck, we will have made our way to Matanzas by this point, but as a fail safe, we plan on spending a night in Pinar de Río. This is the last major city before we arrive in Valle de Viñales, which is our final stop before we eventually turn and head back towards Havana.

The 10th biggest city in Cuba, Pinar de Río is the capital of tobacco country. It was one of the last-founded cities in Cuba, and it was originally called New Philippines, because of all the Filipino laborers that has immigrated here to work on in the tobacco industry. It was renamed Pinar Del Río in 1778, and the rest is history.

This will be a relatively brief stop in our trip, but I'm excited for it. I've always found it to be extremely enriching to visit the more unassuming locations in a country. That's where you'll see real life. It was true in Bac Ninh (Vietnam), it was true in Mandalay (Burma), and I'm hoping that it will be true here and in Matanzas. But who knows! This is an adventure.

Fourth Stop: Valle de Viñales

Valle de Viñales, after Havana maybe, is the destination that I'm most excited to visit. 40(ish) minutes out into the mountains from Pinar del Río is the jewel of Cuban tobacco country. Ever wondered where Cuban cigars come from? This is that place. Er, well, one of them. Tobacco is a cash crop in other parts of Cuba as well. Viñales is famous because of its unique landscape more than anything.

We have found ourselves a homestay here, and plan to spend as much time as possible exploring this alien landscape. There's caves, horse-back riding, food, and most of all, Cuban cigars just waiting to be smoked. I'm not much of a smoker, but I think this is a significant enough occasion to abuse my lungs a little bit. If you want me to bring some back for you, hit me up! 🤜 🤛 💼

From here, it will be time to head back to Havana for the last chapter of our trip.

And then back to Havana

We actually won't have had much time in Havana the first time around, so the bulk of our Havana time will be in these last few days. We've booked a nice Air BnB in Old Havana, but we don't plan on spending much time there. Out in Havana there is an endless supply of historical sites, museums, old churches, and amazing food to keep us busy. Some notable places that are definitely on our list include Ernest Hemingway's old house, the Havana Cathedral, Fabrica de Arte Cubano, and El Morro (an old fortress guarding the entrance to Havana Bay.) Salsa lessons are also in the cards.

Cuba poses a few unique challenges because Americans do not yet have ATM access and functional Internet is pretty much out of the picture, so hopefully we will have budgeted our money well enough to be able to fully immerse ourselves in everything that is happening in Havana. I'm not gonna lie.... the fact that I won't be able to withdraw money if I need it is making me a little nervous, but it'll get figured out. This ain't my first rodeo.

Our Trip, Mapped Out:

Cuba is going to be, logistically speaking, a difficult one to navigate. Or, at least at this point in time, for an American. Hopefully regulations will ease soon, but in the mean time, expect a thorough guide on how to do this to be published in the coming weeks.

On my end, I'll be getting ready to chase down my Bond-villain dreams in the jewel of the Caribbean. It might sound silly, but Havana carries with it an odd McCarthy-era taboo that makes it an exciting destination for me, as an American. It still feels like the forbidden fruit.

But for realz, getting to know the Cuban people is something that I am very much looking forward to. This blog wasn't around back then, but at one point I was studying Spanish in college, living in Madrid, and working a marketing job in Spanish. It's been a few years since I've needed to use that Spanish though, so I'm pretty rusty. And by "pretty rusty" I mean "I'm worried that my Spanish might be gone forever."

If you need me, I'll be relearning everything I forgot.

¡Siguiente Parada: Habana!

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