Reflections on visiting Cuba

Though just an hour flight from Cancun, Havana could not be more different.

Cancun with its long stretches of congested roads, plastered with billboards, lined with banks, restaurants, chintzy shops, tacky night clubs, and currency exchanges; high rise condos, apartment buildings and luxury hotels lining the horizon. An abundance of sex, booze and cement; a total lack of character.

In contrast, upon landing in Cuba and hopping in our first taxi en route to Havana Central, I feel like I´ve not only landed in a new country, but in a different time.

The first thing I notice are the vehicles sharing the road–the vast majority, circa 1950s Chevys and Fords, plus old Soviet model Ladas, and Volgas–belching black smoke. Next, I see a complete lack of advertisements, save for the few featuring hand-painted government propaganda. I see the large dilapidated apartment buildings, a few old factories, and lines of people standing idly along the road, waiting for a bus, or a ride from a kind stranger.

Before even leaving the airport, I was entertained by the uniforms of the female customs agents, which resemble the average promiscuous College Halloween get-up–ridiculously short skirts, fishnet stockings, heels. I will see this throughout the country with female police officers, receptionists, and even with school girl uniforms.


La Habana´s beautifully crumbling buildings


Some car maintenance in front of the Capitol building, La Habana

I notice that nothing looks like its been updated or changed in 50 years–a thin layer of grime covers all; paint peeling, stone crumbling, glass broken. But below the obvious signs of decay, lies structures with incredible architectural integrity. There are big brick or stone buildings with ornate crown molding, vibrant stain glass windows, fluted columns, balconies, statues, dormers.  This gives much of the city a mysterious and magical aire. And though fading and in need of repair, the city has the feel of a place that in some parts still holds that old school glamour you thought only existed in old Hollywood films. Every street I pass brings new curiosities. A television becomes obsolete when I can sit and absorb the life of the city on a well positioned balcony, outdoor cafe or park bench.

Peering down alleys or through doorways and rusty metal gates, I get a glimpse into another world–men gathered around playing dominos, women tirelessly mopping permanently stained tile floors, children playing baseball with scrap wood, and the usual barking dogs and roosters adding to the sounds of vibrant music, to Cubans chatting loudly and to the peculiar honking of ancient horns. I notice the absence of people on laptops, mobile devices, tablets.

My first glimpses into Havana left me wanting more.


The streets of Havana

First a quick diversion

Before and while travelling in Cuba, hoping to gain insight into the embargo–plus the laws which restrict me from legal travel, and the tumultuous relationship between the two countries–I read articles + a book about the history of US-Cuba relations.

For those who need a refresher…
US-Cuba ties date back to the end of Spanish-American War in 1898. Spain, defeated, signs over the rights to Cuba, Puerto Rico, and Guam to the US. Shortly after, the US grants Cuba independence, under the agreement that the US could intervene if necessary and that the US be granted a lease for a Naval Base at Guantanamo Bay.

From that point, all was more or less fine and dandy until the Cuban Revolution in 1959, when Fidel Castro (along with the iconic Che Guevara) overthrows the Batista regime, implementing a Communist Regime. After Castro’s first few years in power, he begins nationalizing private companies (many of which were American-owned), snatching up private land and taxing American products. The US government responds by imposing trade restrictions on all but food and medical supplies. Cuba responds by trading with the Soviet Union instead. The US, enraged, cuts diplomatic ties, and Kennedy issues the first permanent embargo in 1962. Without imports coming in from America, Cuba gets caught in the 60s. This ping-pong match continues for the next 50 years. 

In the years following the embargo, the US makes several unsuccessful attempts to overthrow the Cuban government (Bay of Pigs), and even assassinate Castro (Operation Mongoose). The Cuban Missile Crisis occurs after Kennedy learns of the Cuban Government’s purchase of nuclear weapons (likely in response to the Bay of Pigs attack) from the Soviet Union. After a tense 12 day nuclear face-off between the US and Russia, an agreement is made–the US will remove its missiles in Turkey, and Russia will remove theirs in Cuba. The US keeps its guard up and holds an even tougher grudge.

In the 1980s, economic crisis drives hundreds of thousands of Cubans to seek asylum elsewhere. Many of which hop on boats or hijack airplanes (or ferries) and head for Florida (barely 100 miles away), joining the hundreds of thousands already living there.

Fast forward 20 some years and you can find nearly a million Cubans living in Florida, forming one of the most powerful and influential immigrant (and anti-Castro) groups America has ever seen. With powerful Cuban-American interest groups lobbying hard, every presidential administration since has had to impress with their Cuba policies. Despite the fact these policies have yet to be proven effective, the Clinton and Bush Administrations (not to mention those shady terrorist interrogations at Guantanamo) both added further restrictions to the embargo and restricted travel to both the common American and those with family in Cuba.

After his election in 2008, Obama shut down operations at Guantanamo Bay and opened up travel for Cuban-Americans. Showing for the first time in nearly 50 years, tiny steps toward a more diplomatic relationship, and a willingness to take another look at the ineffective laws that have surely done more harm than good. We´ll see what happens.

Moving on…

Cubans themselves are a fascinating part of the city. Not quite fitting the mold of the stereotypical Latin American. Showing great diversity with African and European roots.

With the government providing free education through University, Cubans are often highly educated. However with that same government limiting internet, and banning most travel, many seem to carry a deep sense of curiosity and longing for a world they cannot yet reach.

A sense of disparity becomes obvious. These are people who, though they receive free education, healthcare, government housing, and a small amount of food rations, make the equivalent of just $480-960 Cuban Pesos (US$20-40) a month. This might not be such an issue if there weren’t two different currencies used in Cuba–the Cuban Peso (approx 1/24 of a dollar) for Cubans, and the convertible peso or CUC ($1CUC=$1US) created for tourist use only. The peso is used in markets, government cafeterias and on public transportation. The CUC is used for shuttles, cafes, restaurants, bars, night clubs, hotels & casas particulares, and other tourism-related places.

During the 5 year span of time, known as the Special Period. The fall of the Soviet Union marked the beginning of a massive economic crisis in Cuba–spreading food and power shortages throughout the island. In response to this financial disaster, the US actually tightened the embargo (as to encourage democracy, of course). People were forced to live without the goods they had become accustomed to and certain changes became necessary–sustainable agriculture was introduced, car and electricity usage decreased. Prior to this time Fidel discouraged tourism.  However due to financial necessity spawning from the Special Period, the industry was able to expand.

A friendship between Castro and newly elected Venezuelan President Hugo Chavez, established a deal in which subsidized oil was traded for Cuban Doctors (Cuba, with their free education system, has an abundance of doctors); and this along with the money pouring in from a newly thriving tourism industry ended the Special Period–though left the Cuban people with some raw wounds.

Much to the disdain of Castro and his fellow revolutionaries, today–due to this tourism industry–a new class of Cubans is rising from the Communist country. The Cubans who run Casa Particulares (or government permitted guesthouses), restaurants or work at hotels or as tour guides, are earning the coveted CUCS; meanwhile doctors, teachers, and everyone else working for the government, continue to earn pesos. With many basic items sold for CUCs, the average Cuban has difficulty affording necessities such as shampoo or toothpaste.

Due to this phenomenon, you may find that your cab driver, casa owner or waiter carries some impressive educational credentials.


One of the government permitted food stands–likely selling ham sandwiches.


Che, old car, government market…Cuba

Myself and my travel companion—Kristi, a spunky fellow Midwesterner–spend our days in Havana walking. Walking up and down the streets of Vedado, Central Habana, and Habana Viejo. On our first evening, we walk along the Malecon, an 8 km long stretch of sidewalk along the sea. We walk past shadowy figures, fondling couples perched on the wall. Groups of men holding half empty bottle of Havana Club kiss the air and praise us as we pass.

No other country in Latin America seems to compare to Cuba on the level of catcalls. And this is really saying something. Latin men are not shy.

At times we are irritated, though mostly we are entertained and must hold ourselves back from laughing. On one occasion, an entire bus filled with Cuban soldiers held up at a stop light simultaneously whistle and hoot as we walk by. Another time an old man playing a trumpet in the street, stops his song, to make kissing noises through his mouthpiece as we walk by.

When we pass the men selling souvenirs in Old Havana, they all try to entice us to come in, “What are you looking for? Purses? Magnets? A boyfriend??” Most commonly, men just stop walking and turn themselves to us, whispering suggestively or telling us they love us.

When we aren’t dealing with the men, we are avoiding the jineteros, or hustlers, skillfully trying to sell us tours, cigars (which were most definitely of a low quality), tickets to a Buena Vista Social Club concert (which surely didn’t exist), or take us to a nice, “cheap,” restaurant or mojito place. These people are often skilled.

In Cuba, you must always bring your travelling A-game. You cannot let your guard down.

It brings me shame to say, one afternoon, I´m ripped off by one of these street artists. Heat and exhaustion cause cloudy thinking as we are scanned into buying ourselves and a few talented jineteros expensive mojitos from a dingy Cuban dive bar. While drinking these watered-down Cuban cocktails, I also somehow am talked into spending too much on what turns out to be cheap cigars. This amateur move costs me a total of $13, along with a great deal of my pride.

Upon leaving the bar, and realizing what has occurred, I angrily storm back into the bar, and yell furiously in Spanish at the bartender. Clearly caught off guard and a bit embarrassed, on the counter he lies a chunk of my money. Still, the incident leaves a sour taste in my mouth.


The shady Havana bar where I was shamefully ripped off…

On our first night, while aimlessly wandering, we meet a group of young Cuban men. One of them, speaking perfect English, insists on giving us an unofficial tour of Havana Viejo, the most popular tourist barrio in town. Cautiously, we follow him as he shows us the perfect plazas framed by impressive, old buildings. We walk past Hemingway’s favorite spot for a mojito, then his favorite for a daiquiri. We see lovely cafes with atmospheric seating in the antique, stone streets. Our guide tells us that most Cubans cannot afford to go to these places, to eat, drink or to hang out.

We ask our new friends where we can find inexpensive food. They take us to one of the plentiful cafeterias, or government permitted food windows, typically run right out of someone’s home. We buy greasy (and delicious) personal pizzas for 10 pesos (or about US 50 cents)–the first of many on our trip. We pay in CUCs, but receive our change in pesos (the standard with government venders geared toward Cubans).

As we eat in the street, one of the men with us is questioned by the police. Our new Cuban friend tells us that the government doesn’t want them interacting with foreigners. I suspect the police may be questioning the man to make sure he isn’t a jinetero. I suppose we will never know for sure.

We decide to spend the evening as Cubans do, so we buy a big bottle of Havana Club rum (for less than US$5) and a couple cans of soda and head for the Malecon. As we polish off the bottle, our new friends answer our questions and tell us about life in Cuba. He tells us about the spies found in every neighborhood, who work for the government and report any mischief or rule breaking. He compares them to a friendlier version of Hitler’s Gestapo.


The romantic plazas of Habana Viejo


You’ll see many dogs wandering around Habana Viejo with tags on their necks. While at first they may appear to just be another ordinary Latin American street dog, these tags show which plaza, museum or monument, or general “zone” for which they belong.


One of many 50 cent pizza consumed while in Cuba


A common image in Cuba, and all of Latin America.

After a lovely breakfast in the breezy pink dining room of our Casa, we spend our first morning wandering to other parts of the city. We head to the Plaza de Revolucion, a series of ugly 1950s cement buildings with the sculptured faces of Cuban Revolutionaries facing what appears to be a massive parking lot with no cars. In this complex, Castro and the Cuban government hold rallies and make big announcements.

After one night in Havana, we spend two nights in Trinidad. Again, wandering up and down the charming stone streets, soaking in the vibrant Caribbean-Colonial buildings, eating cafeteria ice cream, and spending the evenings drinking cheap Cuban wine on the plaza, listening to fantastic live music and meeting other travellers.

One night we end up in a dance club hidden in the depths of a massive cave. Here we dance ourselves sweaty for hours to salsa and latin-techno remixes, stalactites drooping from the high ceiling. At one point the music and lighting changes and handsome, shirtless men emerge from each corner of the dance floor. The crowd of foreigners and Cubans form a circle around the men as they begin a dance resembling a tribal ritual. They grab a girl from the crowd and put her on a table, blindfolding her. They place a large snake around her neck, and then each man crouches near a corner of the table. Using their teeth (and only their teeth), they lift the table and carefully begin walking with it. Things get even more bizarre, after they put the table, the girl and the snake back down, and one of the men smashes a pile of empty beer bottles under a silk cloth and proceeds to eat the glass shards, using water to wash it down.

The following morning, we take a direct shuttle to Viñales, a small scenic town in the heart of the tobacco growing region. Viñales has a 1950s small town feel. Every house well-maintained, usually with a breezy front porch, and rocking chairs. The locals are outwardly pleasant, friendly and helpful, and everywhere is within walking distance. Upon arrival, we welcome ourselves with $1.65 mojitos near the plaza and book a horseback riding tour for the following day.

In the evening, after 50 cent street pizza cooked in a metal barrel turned coal oven (one of the many inventive recycled creations I witnessed in Cuba), we decide to check out the local cinema. We pay 50 cents to see a strange Cuban-made film in a theatre that reminds me of my former Middle School auditorium. A pregnant Cuban woman presses play on a DVD player attached to a projector to begin the film. From what we could understand, the movie featured an elderly man who either A) Learns about the secret Cabaret life of his late wife, who also happened to be cheating on him with a man he later befriends or B) He learns his wife had a twin who was a Cabaret dancer and lover of his new friend. About 5 minutes into the hour and a half film, I’m ready for it to end.

The following morning, along with a few friendly vacationing Brits we take a horseback ride past the lush tobacco fields, cute little palapa barns and farmhouses and strange craggy cliffs rising from the flat terrain. We feel like we have stumbled onto a movie set–everything seems too perfect to be real.

We stop at a tobacco farm and the farmer shows us his plants and informs us of how the best tobacco leaves (and ones used to create the most expensive cigars) grow at the top of the plant, while the leaves growing lower on the stalk produce lower quality and cheaper cigars. He takes us into a barn and shows us how the tobacco is dried and how the cigars are hand rolled. He shows us that the best cigars are rolled using tobacco leaves, and how the cheap cigars are often rolled in a plantain leaf. He then encourages us to buy a pack. When we pass, he encourages us to buy coffee beans, then cocktails. We politely decline.

In the heat of the day we ride to the base of a massive cave, and wander through its dark interior. We are led by a small moustached Cuban man holding a torch. When we reach a small river in the cave, the man leaves us and a light, and says he will return later. We swim in the cool, murky water, our voices echoing into the darkness.


Horseback riding through the tobacco fields near Viñales


The “mini mountains” of Viñales


A tobacco farmer and his fields

The following day after a fast 8 KM walk to an anticlimactic mural painted on a cliff side, we catch a bus to an eco community and nature reserve called Las Terrazas. Here, we stay in bungalows by a green river and spend our time swimming, and walking around the reserve.  We walk into the community. The small town, though claiming to be an Eco-community, seems no different from other small Cuban towns. Though its large, blocky cement apartment buildings, plain houses, and lack of a central plaza or even of citizens doing normal daily activities make it feel even more like a jail or military base. We had already noticed that, except for Havana and the gas guzzling old cars, Cuba felt very environmentally friendly. Though it was clear this was but not due to a collective effort to save the environment, but due to necessity.

While in Las Terrazas, a chatty Cuban tour guide informs us of an important announcement by current ruler Raul Castro–he will be leaving power in 2018, hence ending the 50+ year reign of the Castro brothers. Though this by no means marks the end of Communism in Cuba, this is promising news for the future of the Cuban government and for US-Cuba relations.


Our eco-bungalow

We skip out before staying a second night in Las Terrazas and head back to spend our last 3 nights in Havana.

Our last days in Havana are a blur of long walks interrupted by hours of sitting in parks and plazas people watching and carefully sketching in our notebooks the crumbling old buildings, statues, and fountains. We eat our fill of cheap cafeteria food–pizza, ham sandwiches and ice cream. We spend most of our nights at a brewery and restaurant with massive outdoor seating, overlooking my favorite plaza–a particularly large and clean area featuring a large fountain in the center framed by perfectly restored buildings. This place wins us over with its mugs of decent, cheap, dark beer and nightly live music. We never seem to have the energy or desire to head to the salsa clubs.

On our last night we have one of our only meals which does not feature fast food. At a lively spot in the center Habana Viejo, I order Ropa Vieja, a tasty dish consisting of tender stewed beef and green peppers in a yummy sauce. We wander around the city, looking for something to do, though neither of us is keen on spending any money or on drinking any alcohol.

I think we both realize that somehow Cuba has left us feeling drained and exhausted. We end up back at our casa reading and heading to bed early. It’s an anticlimactic end.

Having experienced Cuba, I’m left feeling a bit torn on the issue of the embargo. Though mostly only for selfish reasons. Opening up trade with Cuba, would undoubtedly improve the lives of Cubans. However allowing more American influence through increased trade and investment would inevitably take away from the island´s old school charm. Clouded by my worst fears, I envision bloated, sunburnt Americans flocking to Cuba´s beaches and demanding the comforts of home; while greedy investors storm the island–opening up massive luxury resorts, casinos and condos and turning it into a mini Cancun.

However, this is a worst-case-scenario, I can’t see these kinds of changes happening quickly. In the meantime I do feel it’s a ridiculous and an ironically undemocratic law to restrict Americans from visiting Cuba (let alone anywhere in the world).

Undoubtedly, a nice change of pace from the routine of travel in Latin America–a break from backpacker hostels, decision fatigue, modern technology, the internet and from “Gangnam Style,” in the end, Im strangely relieved to land back in Mexico. Though Cuba was a fascinating experience–a trip I was glad I took–it left me feeling like a weary traveller.



  1. Fascinating Lindsay! Can’t wait to talk to you more about this adventure (when you eventually make your way home).


  2. OMG Lindsey, you write so beautifully. I love reading your posts and learning so much from you. Thank you.


  3. This is such a fantastic insight to Cuba. I just wrote a post on my experience travelling there and linked your site to it. It really is such a fascinating place. I love the way you write, you’re a great writer!


  4. Hi! I returned from a semester study abroad program in Cuba in the beginning of May and many of my reflections were similar to yours. I’m not sure exactly how long you were there, but I’m thinking it wasn’t three months, so imagine how weary and relieved I felt when I returned to the States in May. My reaction to Cuba can only be described as complex and confusing because my conclusions were anything but decisive and clear. I really enjoyed reading this and plan on sharing it with my friends and family to give them a little insight into what my time in Cuba was like. Thanks for sharing your experiences!


    • Wow 3 months in Cuba! Good for you! Where are you from (what country)?
      I bet that was quite an experience; something that you’ll reflect back on for the rest of your life, I’m sure. I was going to ask if you had a blog, but caught myself–that would be darn near impossible or very expensive 🙂 Thanks so much for reading!


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s