Landing in Havana was, in some ways, surreal for me. This city had been cloaked in political taboo for so long that it occupied a mostly theoretical space in my mind. This sense of taboo was reinforced in the Fort Lauderdale airport as I stood in line after line after line waiting on different pieces of visa documentation. Armed officers had a dog sniff me at security, and then I was on my way.
Seeing rural Cuba fly by as we made our landing in Jose Martí Airport removed this cloak quickly and unceremoniously. Sitting all around us were Cuban–Americans, most of whom (I inferred) were visiting their families back in Cuba, much the same as my family had made the pilgrimage back to New York every Christmas growing up. The 13-year-old boy one seat over told us how he and his parents return to Cuba every year to see his grandparents. Too young to be fully aware of the politics surrounding the flight he was on, we listened as he told us about some of his favorite places in Havana.
After upwards of an hour spent at customs, baggage claim, and changing our Euros for Pesos, we were following our taxi driver through the hot Cuban sun to his car. From the back of his slick 1950s Cadillac, I watched the boonies of Havana fly by as we sped towards the city.
Painted on every wall and billboard was some of the most unabashedly polar political signage that I’ve ever seen.
“Socialismo o Muerte!”
“Cuba Es Nuestro!”
“60 Años De Victoria!”
“Unido Para El Partido”
“Patria o Muerte!”
“Hasta Siempre, Fidel!”
“Continua La Revolucion!”
[ Insert Castro/Guavara Quote Here ]
The list goes on.
Over the course of my trip, this propaganda would go from entertaining, to frustrating, to disturbing fairly quickly… but I’m getting ahead of myself. I’ll talk politics later, but right now, I’m in the back of that taxi, and despite all the build-up this trip had had, all I could think about was how surreal it was to finally be in this country.
“Cuba. Here it is. It’s real. And I’m in it.”
A Quick Introduction To Havana
If you’re an American, Havana’s position in your consciousness may be slightly elevated of late. For me, hardly a weekend goes by that I don’t see colorful flurries of photos of Havana on my Facebook newsfeed. It’s a trendy place to go right now. Everybody is going. Do you know why?
Because America and Cuba are becoming friends again!
That's an over-simplification, but the important part for right now is that America and Cuba have taken an important step towards de-escalation, and as a result, it's a lot easier for gringos like me to get on a plane and visit.
Edit: Whoops, maybe this isn't true anymore. Trump said some stuff, and now things are changing again. I'll continue to cover this as things develop.
Note that "easier" is not the same as "easy"—because it's not. You can read about it in my guide on how Americans can visit Cuba.
So, these photos that people post of Havana usually have the same two features: classic 1950s cars and colorful-but-decrepit European style buildings. Together they are a pretty unmistakable combination, and one that is often taken for granted, but there is a lot of backstory surrounding Havana's peculiar atmosphere.
A Historical Backdrop For Havana:
To look out across the rooftops of Havana today, things look rough. Cuba is pretty far down the economic development ladder… but there was a time when it would have been nearly indistinguishable from Western Europe. The Spanish built Havana to be their satellite capitol—Madrid 2.0—as they pillaged, plundered, and colonized their way through the Americas, from California to Argentina. For Spanish galleons that were bound for the Americas, Havana was the port of choice to stop, rest, re-stock on supplies, and take care of any official government business that required attention. From there, it was the jumping-off point for just about everywhere. On the return voyage, these same Spanish galleons would arrive in Havana's harbor heavy-laden with gold that had been stolen from native peoples across Latin America. This was their last stop before setting sail back across the Atlantic. The decadence and wealth of Havana was legendary during this time, but it wouldn't last.
In 1898, after 20(ish) years of on-again, off-again civil war, the the U.S. intervened, faking an attack on its own troops to rally public support and congressional approval, to help the rebels oust the Spanish from Cuba. Being the last remaining vestige of their former colonial glory, the Spanish has clung to Havana with a death-grip, but there was a new sherif in town. After defeating the Spanish, the U.S. did was it does best: installed a puppet government. With a comfy seat in America's pocket, Cuba's economy developed quickly, and Havana continued to flourish... until the Cuban Revolution.
I'm not going to waste time talking about politics yet. I'm saving that for later, but we should all know the bullet points already. The main thing I want to cover, which is indisputable, is that under Castro's leadership, Havana fell into ruin. 2 world powers had poured their wealth into Havana for nearly 5 centuries, but starting in 1959, maintenance of the city effectively ended. Today, (minus the people and the cars), Havana looks a lot like there was a zombie apocalypse 60 years ago. Buildings that were obviously beautiful and luxurious in the past, are literally falling apart today. But people have been living in them just the same. Some buildings have faired better than others, but during my time in Havana, every time I thought to myself "Okay, that building is so decrepit that it MUST be uninhabited," I would see somebody walk out with a hamper of laundry or something. It's a strange place.
When people ask me how Havana was, my response is always that it was "interesting." It was also good of course! But it was more interesting than it was good. Cuba is a fascinating place where you can feel the geo-political currents swirling around you. I'm going to devote plenty of time to unpacking the political and cultural issues that are at play in Cuba, but first, I want to go through my favorite Havana landmarks. This is my version of your tourist check-list. 📸 🕶️ 🌴
We'll start with Old Havana. It's absolutely iconic, and the first thing about it that I want to impress upon all you readers out there, is that it's actually pretty damn large. In the grand scheme of the Havana map it doesn't look very big... but size is relative. As a whole, Havana is HUGE! It's the biggest city in the Caribbean, and even the smaller neighborhoods within it's municipal limits are quite large. I had expected "Old Havana" to be small and overrun with tourists, but what I found was a pleasant surprise. It turned out to be too expansive to be "filled" with tourists in any noticeable way. Of course there were certain city squares where white people would congregate to have a few beers and listen to live Salsa music, but it didn't take much walking to be completely immersed in Old Havana as it has always been.
Walking through the streets of Old Havana for the first time was overwhelming to me. It was everything I had hoped it would be and more. What was once a thriving European city had fallen to ruin, leaving behind an endlessly interesting maze of vibrant urban decay. Cool ocean breeze filled the alleyways every few moments, chasing away the heat of the hot Cuban sun. Brightly colored paint peeled off of the walls of the narrow, cobblestone alleyways, which were filled with the classic Oldsmobiles that Havana has become famous for. I was suspicious that these cars would not be so prevalent as I had been lead to believe, but these suspicions quickly proved themselves to be baseless; these cars were everywhere. However, the most interesting layer at play in Old Havana (as well as in the rest of the city at large) was that in spite of the city's rotting infrastructure, life still went on as normal!
Some buildings were better maintained than others, but ALL of them were full of Cuban families, just going through their daily routines. In the case of some particularly run-down buildings, it was a little shocking. Seriously, some of these buildings looked like shots out of Aleppo. Still, others hadn't fallen far from their former glory. Every city block was a mixed back, riddled with tree roots and adorned with hanging laundry.
Walking around Old Havana left me with more questions than answers. There was a LOT to unpack here! I'll go deeper beneath the surface of this fascinating city in later articles, but for now, I just want to take a few minutes to appreciate how beautiful Old Havana is. Check out these photos...
Daytime In Old Havana ☀️
Twilight In Old Havana 🌆
Night In Old Havana 🌖
Havana's Malecón is, unquestionably, the most iconic street in Cuba. This is the street that runs the length of Havana'a waterfront, starting in Old Havana, and stretching eastward past Vedado and Miramar (neighborhoods of Havana). Havana is a densely packed urban city, leaving little room for major streets. This makes the Malecón one of Havana's biggest arteries. It's the quickest route for drive back and forth across Havana, so if you come to Havana and spend any amount of time traveling by taxi, you're sure to be on this road a lot. But the Malecón is more than just a road...
The Malecón is also a protective seawall, blocking the formidable waves that come crashing towards Havana off the Atlantic Ocean. In some places, these waves crash so high that people walking on the sidewalk are in danger of getting doused in sea water. When storms come blowing into the Cuban capital, this is not where you want to be standing. However, on nicer nights, this is exactly where you want to be.
By night, the Malecón is a social hotspot for locals. Instead of spending the money to go to a salsa club or a restaurant, Havana's "average Joe" will come here. On any given night of the week, the Malecón will be packed with people. Some may be drinking, playing music, or dancing. Others might be enjoying a romantic evening. You might even find leftover fishermen casting lines who are leftover from daylight hours. The entire street is lined with a huge concrete siding / platform that is perfect for sitting. It's a great spot to walk, enjoy the sunset, and get a feel for what real life looks like in Havana. Here are a few pictures of the Malecón in various stages of daylight and weather...
El Capitolio—or, in English, the National Capitol Building—is the historic seat of political power in Cuba. Designed by an American architectural firm in the style of the United States' own capitol, it was here that Cuba's Congress operated right up until the Cuban Revolution in 1959. When Castro took power, Congress was disbanded and this building was vacated for a period of time. In later years, it would be repurposed to house Cuba's Ministry of Science, Technology and the Environment.
This building was, for a while, the tallest structure in all of Havana. It towers over Old Havana, visible on the horizon of many alleyways that run westward towards the building. You'll see its dome poking out at the end of alleys and streets in photos from Old Havana ⬆️ above. It's easy to get lost in Old Havana, but this dome is a navigational North Star, often visible above the rooftops or at the end of streets. Sitting next Gran Teatro de la Habana, as well as a large number of other historic buildings, this plaza is a tourist haven during the day. By night however, this plaza empties, which left us to wander in peace, enjoying the warm, salty Havana nightime air.
You'll notice that it's under construction right now. This is one of the best-maintained buildings in the entire city—it's almost out of place with how non-decrepit it is. We had wanted to go in, but it was closed during our visit, so all you get are these choice pictures from the outside of the building. Sorry!
Museum of the Revolution
This is a super important piece of the puzzle that is Cuba, so I'm gong to circle back and give it its own article later on in our progression. If you haven't already subscribed to this blog, you can do so right here — then you'll get an email when this article is finally published. 👍
Hotel Nacional de Cuba
Sitting atop Taganana Hill and the Santa Clara Battery, which is particularly well-fortified area of the Malecón with historical military significance, is Hotel Nacional de Cuba. Facing the ocean in front of the hotel, amongst patio seating for the bar, are gigantic (and real) military guns dating back to the 1800s. The hotel itself is a prime example of Gatsby-era extravagance, although to walk its halls today, it definitely feels like a relic. The lobby of this historic establishment features very dated indicators of wealth, like gaudy chandeliers and waiters in tuxedos. Despite the fact that nobody was smoking, the entire establishment carried the faint odor of cigarettes, perhaps a lingering vestige from the 1950s. It's kind of like Wes Anderson's Hotel Budapest in these ways, except with a lot more guests.
Constructed by an architectural firm from New York City, this hotel officially opened its doors in 1930 under American management, just in time for the heyday of American's in Cuba. Between the opening of this hotel and the Cuban revolution almost 30 years later, Wealthy Americans poured into Havana. During this time, Havana was the Paris of the Caribbean, attracting notable American intellectuals such as Ernest Hemmingway, who's Havana-home has become a tourist attraction in its own rite. (I never bothered to go there though). Havana was also notably a hang-out America's prohibition-era gangsters. Needless to say, there was a lot of debauchery that occurred in Havana thanks to visiting Americans, but that came to a swift and violent end with the Cuba revolution in 1959. After that, the foreigners, their money, and the lavish parties they threw disappeared, but this hotel remained.
In the past few years, business for Hotel Nacional has been good, and the recent influx of Americans into Cuba again is starting to bolster Havana's hospitality industry at large. However, it might never be what it was. There are clear pros and cons here, but to truly understand them for yourself, you'll just have to visit.
University of Havana
Sitting atop a hill in the residential neighborhood of Vedado is the University of Havana. The campus isn't quite a sizable as many Universities in the developed world, but the architecture is stunning nevertheless. Much the same as Harvard, Oxford (and pretty much any other illustrious university that might spring into your mind for a comparison), the University of Havana is chock-full of old European-style buildings where classes are held everyday.
At its founding in 1758, it was originally called Real y Pontificia Universidad de San Gerónimo de la Habana, but as Cuba progressed and things changed, it was renamed to Real y Literaria Universidad de La Habana... and then renamed again to Universidad Nacional... until finally things settled on Universidad de Habana. So, this is a university with some serious history behind it. It has many important alumni, including Fidel Castro himself! In fact, this university played an important role in the earliest days of the Cuban Revolution. Indeed, under (former) President Batista, the University of Havana was a place of radical ideas and protests. During Castro's formative years, he was an active part of this politically community. A lot happened between Castro's time in college and the Revolution, but this University still stands tall.
We arrived at the University shortly after business hours. The sun was starting to slide lower in the sky, but twilight had not yet settled over the city. Hoping to walk through a few of the beautiful buildings and perhaps even catch a glimpse of classes that were in session, we quickly found our way to the school's gates, but when we arrived, we were turned away. The security guard told us (translated) that we would have to return the following day before 5:00pm to go into the school. A little disappointed, we continued walking through the school. Outside the student union we found troops of students rehearsing a dance routine. Aged, wise-looking professors walked out to their classic Oldsmobile cars parked on cobble stone streets. One car in particular struck me as photogenic so I set about having a mini-photoshoot with it. The professor who owned it actually came out in the middle of this photoshoot but smiled and told me to continue. I awkwardly snapped a couple more pictures, thanked him, and then scuffled off.
Walking further up the hill to the far side of the university, we peered through a fence to see students playing soccer (er, I mean football) on a huge turf field down below. From the top of the hill, you could see out across Havana to the ocean. In the fading evening heat, I remember thinking how routine it all felt—not so different from my own university experience. I could see myself down on those turf fields. This was more of a revelation to me than I would have liked. Apparently I had come to Cuba expecting the worst, but this wasn't so bad. Life goes on.
Cementario de Cristóbal Colón
Further out into the large expanses of Vedado, sits el Cementario de Cristóbal Colón, or Christopher Columbus Cemetery. Columbus spent a lot of time in Havana during the later years of his life, but he's not buried here. The occupying Spanish forces just saw fit to name this place after him when the cemetery was founded in 1876. However, the cemetery is home to many other notable (and deceased) characters from the more recent chapters of Cuba's narrative, including Ibrahim Ferrer. He was a notable member of Buena Vista Social Club, and is the "track of the day" today.
Today this cemetery is massive, but it was originally much smaller. Ground was first broken to build this cemetery in 1806—at that point it was called the Espada cemetery—but Cholera outbreak of 1868 highlighted the need for more space. So they expanded it! Presently, it spans almost 12 city blocks and includes 800,000 tombs. It's like the central park of graveyards. It is considered to be the second most historically significant graveyard in all of Latin America, behind La Recoleta in Buenos Aires.
The tombs within this graveyard are separated by their inhabitants, much the same as neighborhoods in a city. These "neighborhoods" include separate spaces for priests, soldiers, brotherhoods, the rich, the poor, infants/small children, victims of epidemics, pagans, and the condemned. However, for as big as this cemetery is, demand for burials here far exceeds the supply of space. For this reason, the remains of the recently-buried are often only kept in the cemetery for 3 years before they are boxed up and sent to a separate storage facility to make room for more dead people. I'm not a cemetery expert... but that strikes me as being kind of irreverent. Anyway, here's a map to show you how big this place is in the context of the city:
This cemetery is surrounded by a huge yellow wall, and even though there are quite a few different gates, tourists can pretty much only enter through one of them. I've taken the liberty of marking that on the map for you ⬆️ up above. In the hot Havana sun, I was very irked to be turned away and forced to walk to the far side of the cemetery. With zero trees for shade and not much sidewalk, I was being cooked against that yellow wall as I walked. I was not in a good mood by the time I reached the correct gate.
Entry into the cemetery costs 5 CUC (5 USD) for foreigners. Inside the cemetery, small streets run back and forth in a grid system, enabling visitors to get a good look at every tomb. There are street signs and everything! In classic Latin American fashion, the tombs are above ground. They are mostly made of white stone, which, in the bright Cuban sun, a near blinding without a good pair of sunglasses. I was grateful to find a bench under the shade of a lone tree. Here are a few pictures I took during my wanderings through this city of tombs...
This was not quite the extent of our touristy activities in Havana—we also went to other (less notable) landmarks, but I made an executive decision to leave them out of this article. We also missed 2 major items on the normal Havana itinerary: Hemmingway's House and El Morro.
Hemmingway's House, as the name suggests, was the abode of the famous writer, Ernest Hemmingway, during the years he spent living in Havana. Hemmingway was a fascinating character and a great writer, but seeing his house was an activity that had received nearly universally bad reviews from our friends who had been there. That alone wouldn't have been much deterrence, but there was also the issues of location. Hemmingway's House is pretty far removed from Havana proper. It was also going to be a long, expensive cab ride to get out there, so we skipped it.
El Morro was something that I had really wanted to see! However, during our time in Havana, the tunnel connecting the western side of Havana's bay to the eastern side was closed for construction. This would have forced us to take another long (50+ min), and expensive taxi ride around the bay to get there. The ferry across the bay could have saved us some money, but to be completely honest, I was tired. #sorrynotsorry. If you want to see a picture, Google it!
Coming up next, we'll look at Havana from a different, more residential angle. Neighborhoods, nightlife, restaurants—all that good stuff. In the meantime, here's a famous track from Buena Vista Social Club's Ibrahim Ferrer. You might recognize his picture from the headstone in el Cementario de Cristóbal Colón.