Skip to content

Visiting Cuba in 2020: A Look Beneath the Gilded Surface

cuban girl smoking cigar

This past Christmas my family and I traveled to Cuba for the first time. We toured three of the island’s major destinations, Havana, Varadero, and Trinidad, on a private tour intended to show foreign tourists “the best of Cuba”. Upon my return, everyone kept asking me, “How was Cuba, was it amazing?!” expecting the answer to be a resounding “of course, it was incredible!” and then move on to other topics. However, when confronted with the same question time and time again, I found myself unable to honestly offer the simple answer everyone was expecting to hear.

The truth of the matter is that Cuba, a country that was clearly once beautiful and brimming with culture and passion, is not the dreamy Caribbean fairytale that I had imagined. Instead, it’s a country that’s simply been frozen in time, a destination permanently stuck in yesteryear and under the total rule of modern communism. As tourists, we were only intended to see the shiny, gilded version of Cuba that the government and tourism ministry wanted us to see, while supposedly being shielded from the reality of crumbling buildings, crippling poverty, and complete lack of both physical and financial mobility. And while we enjoyed the sanitized vacation we were supposed to have, it was absolutely impossible to deny the bleak reality.

kids playing in havana, cuba

Local kids playing basketball in Havana, Cuba

Now that I’ve returned from Cuba and have had some time to reflect, the experience I want to share with you needs to delve beyond the typical “I went to Cuba and had a great time” narrative, and instead expose the truth about the day-to-day circumstances of current Cuban life. It’s time the world took notice and gained some awareness about what’s going on in this seductively mysterious, and for Americans, somewhat forbidden destination, because the truth of the matter is that many people really just don’t know.

Though it wasn’t as I expected it to be, I’m grateful to have had such a unique and worthwhile experience in Cuba and I would encourage all that want to venture out and explore the country do it, though in a mindful and responsible way. It’s important to note that though the country has fallen on hard times, the spirit of the Cuban people is still very much alive and their culture lives on and thrives regardless of the circumstances.

It’s worth it to connect with the people, immerse yourself in the culture, push yourself to see what’s actually there instead of just what the tourism ministry and government want you to see. Share what you have, bring small but useful gifts, learn from the people and let them learn from you. Let your visit become a necessary and eye opening cultural exchange on both sides and think critically about what you are experiencing. It’s time for the world to look beneath Cuba’s thinly gilded surface and discover the truth about what is really going on there.

Cuban propaganda in Havana

Typical example of communist revolution propaganda on a Havana street

The rest of this article will expand on my experience in Cuba, the logistical process of visiting Cuba as an American tourist (it’s much easier than you think!), and my tips for visiting Cuba in a responsible and meaningful way given the current political climate in Cuba and it’s rocky relations with the US. If you’re considering a trip to Cuba, I would 100% encourage you to go, but go as an educated and informed visitor who can experience the country through a more culturally and socially appropriate lens.

My Experience in Cuba

We arrived in Havana on Christmas Eve to experience our first taste of Cuba. We stayed in a casa particular, a Cuban version of a bed and breakfast sanctioned by the government. As we drove into the city, I was immediately shocked by the state of disarray of the buildings and infrastructure. Havana is a city of crumbling 1950s-style buildings in faded pastel colors alongside the coast of a stormy sea. It was clear that at some point in history, this must have been a spectacular place, bright and full of life, but that it had been left that way and its beauty and vibrance had been worn away by time. Though our casa particular was a gorgeous old colonial home with plenty of rooms, high ceilings, and stunning colonial furniture, just outside our door were tons and tons of crumbling one-room apartments packed together and filled to the brim with people. We discovered that the house we were staying in actually belonged to a close friend and colleague of Fidel Castro. That was my first indication that the tour we were on was designed to be a facade for us, to show us the Cuba that the government wants tourists and the world to recognize, and to encourage us to ignore the crumbling, jam packed buildings the locals are living in just outside our door.

There was no WiFi or really any way for us to make contact with the outside world once we arrived in Havana, and we were forced to be genuinely present and experience what was all around us. I took a stroll down the Paseo del Prado, a wide, tree-lined pedestrian walkway through Old Havana. I breathed in the warm, tropical air while a salty breeze tousled my hair, and I looked on as locals and tourists alike enjoyed the fading light of the afternoon. Classic 1950s-style cars cruised by on either side of the paseo and I was totally at ease. It may be crumbling, but for what it’s worth, Havana sure is beautiful.

During the rest of our time in Havana, we took a tour of the city’s main sites in a vintage American convertible, strolled through the streets of Old Havana, and admired the Spanish-style colonial plazas throughout the city. At night, we dined in paladares, which are essentially government sanctioned restaurants where people use parts of their homes as restaurants to serve tourists. Some paladares even serve food on their own family’s antique china and silverware. I loved the idea of this, especially because I knew that eating at these types of restaurants would directly benefit the local families when we paid in CUC, the tourist-only currency. However, I was disappointed to discover that there were never any local Cubans dining at paladares or restaurants, and there were often few, if any Cuban dishes served on the menus, since restaurants were catering almost exclusively to foreign visitors and opted for basic international dishes, like pizza, spaghetti, and burgers instead. 

We stopped into bars with live bands playing and dancing to traditional Cuban music which finally brought to life the Cuba I had always dreamt of. The passion and joy of Cuban music and dance exposed a fire within the people, and I realized that despite the state of things, the Cuban spirit is still vibrant and bright. As we explored the streets of Havana a bit on our own, just a block or two outside of the main tourist areas, we were suddenly thrown into the real, authentic Cuba, frequented exclusively by locals. 

It was hot, so people left their doors and windows open and we were able to peak in as we walked by which gave us a unique sense for what it’s like to really live there. We were totally ignored by the locals as they went about their lives, happily talking and laughing and playing without a worry in the world. They live humble lives, but they make the most of what they have.

classic cars in old havana, cuba

Classic cars in Old Havana

We took a walking tour of Havana with a wonderful local tour guide who, without much prompting at all, decided to ditch the scripted, government approved tour of Havana he was supposed to give, and instead shed light on the actual situation in regards to daily life in Cuba. His depiction of the reality surrounding us was shocking to me, especially since I knew he faced serious repercussions if the police, army, or any government official caught him speaking out, and particularly to foreign tourists. When I asked why he wasn’t afraid to be telling us all of these things, he said that he was so fed up with the government and the communist system that he no longer cared what happened to him…I did notice he stopped talking while we walked past a police officer, though. Another of our tour guides in Havana had joked that if there are two million people in Cuba, there are one million police officers. Though he said it in jest, it did reveal the genuine local sentiment: people feel like the government is everywhere, watching them and policing them at every turn; that they’re there to control the people instead of protect them.

What I failed to understand before visiting Cuba is that it truly is a communist country, something I don’t think I realized actually still existed in the modern world, having grown up in an American democracy. The communist propaganda and messages that bombard you everywhere you look, from the bustling streets of Havana to towering billboards in the desolate countryside, promote the communist revolution of the 1950s as though it’s a modern accomplishment. Signs and slogans everywhere praise figures like Fidel Castro and Che Guevara as “heroes of the revolution” and the “saviors of Cuba”. To me it seemed absurd that a conquest of over 70 years ago still plays such a major part in Cuba’s day to day existence. Our Havana guide painted a picture of an overwhelming sense of disillusionment and frustration with regard to communism. He suggested that the older locals seem quietly disappointed, especially those who initially believed that the revolution would bring prosperity to their beloved country and who had worked hard towards that vision, have now been left behind and forgotten by the government who swore to improve their lives.

Havana street corner

I was surprised to learn that modern day Cuba utilizes a double currency system, which means that locals use and earn in Cuban pesos, also referred to as “moneda nacional” or “CUP” and tourists visiting the country deal in “CUC,” or the “convertible peso.” The primary difference between the two currencies is that the value of the CUC is equivalent to the US dollar, while the CUP is worth much less, the current rate being about 25 CUP for 1 CUC. The big issue with this double currency system is that only Cubans who work in the tourist industry have any financial mobility within the country. People who get paid by the government receive their monthly earnings in CUP, and professions like doctors, lawyers, and accountants will earn less than $20 USD per month, according to our guide, who had studied at Havana University and had previously been a lawyer. For him and others like him, it’s more valuable to work in the tourist industry than in any other government-paid profession because they can at least earn money that has some value on top of tips from foreign visitors.

As I spoke with more locals throughout the country, I learned more and more details about civic life in Cuba. In regard to the shockingly low salaries of most non-tourism industry jobs in Cuba, it’s important to remember that the government is communist and therefore does take care of things like housing, healthcare, and basic food through a rationing system. However, Cuban healthcare is in shambles, with many hospitals operating without running water and electricity and insufficient supplies. So basically, if you get sick in Cuba (which we actually did), you’re screwed.

As far as food provided from the government is concerned, every household receives a ration card with a certain allotment of the absolute basic necessities, including rice, grains, oil, sugar, salt, coffee, and a small ration of meat. In order to receive these basic rations, Cubans have to wait in long lines and show their card, but if the ration stand has run out by the time they get to the front of the line, they have to go find another stand and wait in that line to try to get what they need. All other things beyond the basic necessities, including things like toilet paper, soap, beer, etc. must be paid for out of pocket at local bodegas or found on the black market, which is a necessary risk many Cubans must take. These are just some of the things I learned from locals who were gracious and courageous enough to talk to me, and they’re things that can’t be ignored in any discussion regarding Cuba.

Street art propaganda in Trinidad- Portrait of Che Guevara

The last leg of our trip was spent in the seaside town of Varadero, where we stayed at an all-inclusive resort. Though the resort was similar to something you might experience in any other Caribbean island, it was a bit more run down and had its own set of difficulties. Though it was all-inclusive, there were two specialized restaurants at the resort that you could make reservations for ahead of time. Though the restaurants themselves had the capacity to host many of the resort’s visitors, they would only allow around 10 people to dine there each night, as there wasn’t enough food available to serve more than that amount of visitors.

It was this lack of food in a presumably “all-inclusive” resort along with the lack of Cuban diners and cuisine at restaurants throughout the country that brought me to the sad realization that in some ways, true Cuban culture is actually being better preserved outside of Cuba. The Cuban expat community living outside the country has more of a capacity to maintain their rich culture due to the lack of resources necessary to preserve it from the inside.

classic car tour of Havana

My dad and I on a classic 1950s convertible tour of Havana

Before personally visiting Cuba, I had conjured up images in my mind of this untouched, exciting, fascinating place, which had largely been derived from Instagram influencers and movies like Fast and Furious; I had no idea that there is so much more to Cuba’s story than what meets the eye. When confronted with the reality, I was shocked and somewhat disappointed by my own ignorance. I felt guilty visiting Cuba as a tourist; guilty enjoying all the luxuries of a touristic vacation with my family while the people serving us likely won’t make enough money to ever become tourists themselves, or even eat at the restaurants they are serving in. That said, it’s clear that tourism is a necessary evil in Cuba, as it does benefit the people directly and the country as a whole, so visiting Cuba as a tourist is a bit of a double-edged sword.

Despite all of that, traveling to Cuba opened my eyes to a different culture, way of life, and human experience that has expanded my world view. I’m grateful to have had such a unique and enriching experience, and would gladly encourage others to explore Cuba for themselves, though to do so with a more socially and culturally conscious perspective.

The Process of Visiting Cuba as an American Tourist

Due to Cuba’s rocky relations with the US, it’s normal to think you may have a difficult or near impossible time traveling to Cuba as an American tourist. In reality, though, it’s actually much easier to visit Cuba than you might think. 

As far as logistics go, we took a direct flight from Atlanta to Havana on Delta Airlines without a problem, and we were able to book our ticket online the same as normal. Delta also sells you a Cuban Tourist Card at the counter when you check-in at the Atlanta airport and it costs USD $50 per person. They also have you fill out some forms which specify the purpose of your trip (there are 12 possible accepted “purposes” to visit Cuba which include journalism, family visits, professional research, educational activities, and a few more, but pure “tourism” from America is not allowed). We marked that the reason for our trip to Cuba was “support of the Cuban people,” which is one of the authorized categories. 

At some point in the process at the airport you also fill out a visa form with your name, birth date, and passport number, and take that with you to Cuba.  It is all very easy and the airline provides what you need at the airport, there is nothing you need to do in advance. You should call to double check with airline if you’re not flying Delta, but it was a pretty easy process for us. Once you arrive in Cuba it’s completely like entering any other foreign country at the airport and no problem at all. Your boarding pass from the airline serves as your health insurance card while you are in Cuba, so make sure to hold onto it.  However, you will not want to use the Cuban medical system unless you’re literally dying, so don’t get sick and come prepared with things to cure yourself. Also make sure you get the appropriate vaccinations before your trip if you don’t have them already. 

local havana fruit stand

Local Havana fruit stand

Your American credit cards will not work at all anywhere in Cuba, nor will your ATM cards.  Bring Canadian cash with you to convert on arrival and bring enough to fund your entire trip. Every meal that is not included, every drink, every purchase, must be made in cash.  Americans are not used to this, so you’ll need to prepare for that.  It’s better to bring Canadian cash to convert to CUC because there is a 10% tax if you bring American cash to exchange in Cuba.  Exchanging money should be done right away when you enter. There are two currencies in Cuba – local (CUP) and tourist (CUC). You will use CUC. It is 1 CUC for every U.S. Dollar. A Canadian dollar is worth less than 1 CUC. 

Trying to exchange currency at the Havana airport is not ideal as there are long lines and it’s just not worth the wait. If you have a guide or taxi driver picking you up from the airport, have them bring you to a less crowded local currency exchange in Havana which will be much more manageable.  Once you’ve exchanged money for the first time and you’ve got the hang of it, you’ll be able to exchange cash as you go much more comfortably. Be sure to separate your funds into different secure parts of your luggage to avoid having all your cash getting lost or stolen, because then you’ll really be out of luck!

Note that when in Cuba, you will basically be completely “off the grid” the entire time. There is minimal access to WiFi throughout the island, and even when you have it, it’s very spotty. You can purchase WiFi cards at designated shops throughout the country but they can only be used in public WiFi zones, which are few and far between, but will be marked by signs or by groups of people all using their phones in a certain area! This is something I definitely wasn’t used to and thought I would be much more uncomfortable with, but in the end it was actually nice to just unplug and let myself live in the moment. We had a phone with a small amount of data to use for emergencies, which was provided by our tour company and which actually did end up coming in handy.

We had a set of tours and guides set up before we left and we used Anywhere Inc. to organize everything which was great – they were reliable, efficient, and helped us with anything we needed. Our itinerary gave us a good overview of Cuba and we got to see several different parts of the country in a short time.  Some of the classic touristy highlights that were fun and worthwhile were touring the major sites in an old convertible in Havana, taking a walking tour of Old Havana, walking along Havana’s infamous Malecón, exploring the smaller town of Trinidad, driving through large parts of the Island and experiencing the small towns and villages there, and visiting a beach resort in Varadero. This was a good mixture for us to get the general flavor of the country. 

Tour guides and drivers can be very informative and honest about Cuba, or just give you the standard government approved tour. Both are interesting and worth noting. The last few days we spent at an all-inclusive beach resort in Varadero, on the north side of Cuba. It was beautiful and there was good service, but the resort was a little run down and not especially Cuban…I felt a little guilty vacationing there as a foreigner. We noticed that almost no Americans are in or visiting Cuba, and we mostly ran into people from Canada, Russia, Europe, and China. 

classic car in cuba

Classic vintage car in the streets of Trinidad, Cuba

We stayed in casas particulares, which are like home stays with local Cubans who rent out some of the rooms in their homes and run it like a bed and breakfast.  Americans may be required to stay at these places instead of hotels, but truthfully they’re much more interesting anyway and make you feel like you are part of the place.  These casas particulares are basically large old homes that have been divided into rooms, and the caretakers and owners live in some of the other rooms.  They provide a good breakfast each morning, which may be your best meal of the day. The people are local, interesting, friendly and offer a much more personal experience than a hotel stay would.  

Though relations are tense between the US and Cuban governments, once you arrive in Cuba you won’t feel any hostility from the Cuban people when they find out you’re American. This was something I was a little bit worried about before visiting, and I was considering telling people we were from Canada instead to reduce tensions. However, I quickly realized, both from the general attitude and from Cuban people literally telling me, that it’s really just the Cuban and American governments that have a problem with each other but the people have no issue at all, and they were nothing but friendly and warm to us regardless of our nationality.

el floridita, famous hemingway bar in havana

El Floridita is a famous Havana bar that was frequented by Ernest Hemingway

My Tips for Visiting Cuba

There are a few things you should note to help make your time in Cuba as meaningful and easy as possible. Here are my top suggestions for your trip: 

1.  Bring small gifts! It’s no secret that communism leaves Cuba’s general populace without much of what it needs. Items like simple medications, socks, shoes, granola bars and non-perishable foods, candies, and kids games and toys are seriously lacking throughout the country and are really appreciated whenever you can give them. That said, Cubans are a particularly proud group of people, so you’ll need to be sure to offer your gifts in a polite and dignified way. Form relationships with the people you choose to give to, such as cab or private drivers, homestay hosts, and tour guides. I’ll say that the exception to that rule is with candies (dulces) and little games (juegos) like jacks or bouncy balls; pass them out to kids on the streets or as a kind gesture wherever you go. Oftentimes adults will see you offering candies and games to kids and will ask you for a few for themselves and their kids and grandkids. It’s not a necessity, but it’s a novelty and fun way to brighten someone’s day and have some nice interactions with the locals. Also be sure to leave actual cash tips in CUC for drivers, housekeepers, and service people at hotels, restaurants, and on tours. As a general note, always be respectful and try your best not to waste food.

We are Jewish, so we visited a local synagogue in Havana where we were able to donate a lot of items, like socks, bandaids, Ibuprofen, toothbrushes, shaving materials (any type of medication is particularly useful and appreciated). If you are Christian or are just looking for a place to feel more comfortable donating items you’ve brought, I’m sure churches and religious organizations would be happy to take them and will disseminate them to their respective communities in need.  

2. Learn some Spanish before you go. You will have a muuuuch easier experience in Cuba if you take the time to learn even just a few basic phrases in Spanish. Not only will you be better received by the locals just for trying, but you’ll need it to get by as the majority of Cubans speak little to no English. Do yourself a favor and learn the basics!

3. DO NOT drink the water and be careful with the food (especially meat)!  Though you’ll be fine showering and brushing your teeth with the tap water in Cuba, don’t drink it, opt for bottled water instead. The food can also be dicey, even in crowded restaurants.  My best advice is to keep your diet simple while there to avoid eating anything funky.

My brother, sister, and I all got a horrible case of food poisoning in the city of Trinidad and the running water in our homestay wasn’t working…you can imagine what a rough couple days that was! It turned out to be the meat we had at a relatively nice restaurant. Red meat is a bit of a luxury in Cuba and not a terribly common thing to eat there due to the lack of supply, so we probably should have avoided it in the first place. (Pro-tip, if you end up getting food poisoning and don’t have any electrolyte packets to help your body absorb the water you’re drinking, make yourself a mixture of salt, sugar, and water to help rehydrate you. Shout out to my sister who learned that in college and saved all of us in Cuba!!)

You’ll want to bring anything you might need in order to take care of yourself medically, don’t plan on there being any reliable medical care at all. Hospitals often don’t have supplies or running water, so if something happens to you, you’re kind of on your own. Useful things to bring are electrolyte powder packets to mix with water to rehydrate you if you get sick, activated charcoal pills, Ibuprofen, Pepto-Bismol, Tums, motion sickness medications, cough drops, emergency medications and extras, etc. 

4. Watch how you dress. Cuba can be a little confusing as far as what to wear because on the one hand, skimpy outfits and thong bikinis are commonplace at the beach and along the coast, but with the country’s Catholic roots, as in many Latin American countries, it’s better to dress relatively conservatively. This will also decrease (but not eliminate) the catcalling and excessive unwarranted attention from men on the street.  

5. Embrace the lack of WiFi and communication with the outside world and become truly present. Take this unique opportunity to live in the moment and let yourself just appreciate a genuinely real experience, which can be hard to come by in the modern age.

havana buildings

Havana street

Cuba is a beautiful and complicated place. If you plan to visit, I urge you to look beyond the country’s thinly gilded surface and take note of what is really there. Cuba is relatively safe, but filled with poverty and a crumbling infrastructure. People whose families have found favor with the government live marginally better lives than those with no communist ties at all. Freedom of speech is restricted and it’s nearly impossible for Cubans within the country to make social and financial progress. Though all of these issues undoubtedly plague this sun drenched Caribbean nation, the heart and resilience of the Cuban people is as strong as ever. These people’s spirit will not be broken, no matter what types of hardships befall them; from a simple visit, that much was made clear to me. The people dance and sing and smoke cigars and enjoy life regardless of their circumstances. I am impressed and proud of the Cuban people for not allowing themselves to be broken by the system, and I’m hopeful that one day Cuba will be truly free. ¡Viva una Cuba libre!

*Please note that some of the above are affiliate links. At no additional cost to you, I make a small commission if you choose to make a purchase. Please know that I ONLY recommend products that I personally use or believe to be helpful to other travelers.