What to Expect When Traveling to Cuba for the First Time

Cuba is known for a lot of things: classic 1950s Chevys; beautiful beaches; and being one of the few openly Communist countries left in the world. While only 90 miles off the coast of Florida, Cuba is in many ways a world away from what many foreign visitors (Americans especially) may expect.

In this Country Guide, I will be focusing primarily on what to expect when you travel to Cuba, particularly as an American citizen. I will also touch on the best things to see and do and how best to enjoy this unique country.

Read on for some things to know before traveling to Cuba!

Calle Infanta, Havana, Cuba


Cuba is an island nation in the Caribbean. Originally occupied by Native groups like the Taino, the Spanish arrived in the late-1400s and engaged in a widespread invasion and colonization of the island. The Spanish named the island “The Jewel of the Caribbean,” and while it’s pretty audacious for colonizers to call it that, it is true: Cuba is a beautiful island in a sea full of beautiful islands.

Once a successful country on par with the US economy, Cuba today has a very palpable feeling of faded glory. This is in some ways due to the Communist Revolution of 1959, in which Fidel Castro ousted dictator Fulgencio Batista. While the colorful facade of neighborhoods like Havana Vieja (“Old Havana”) masks a much more decrepit reality, there are certain upsides: Cuba is a very safe and rather educated country, with very high literacy rates and some of the most doctors per capita in the world. Education is paid for by the government, and rent and utilities are purposefully kept affordable.

As a Cuban citizen, you may never have the fanciest car or the biggest house. But you have the confidence that you are highly unlikely to become homeless or have to resort to violence out of desperation.

Getting to Cuba

From the US, the “Legal” Way

Flying from the US to Cuba is not difficult, but it is an odd process. Remember that there is an active embargo against Cuba, so you can’t just get up and go (although the entire rest of the world is able to do just that). You must declare one of 12 reasons for wanting to go to Cuba, none of which is plain old “tourism.” The 12 categories are as follows:

  1. Family visits
  2. Official business of the U.S. government, foreign governments, and certain intergovernmental organizations
  3. Journalistic activity
  4. Professional research and professional meetings
  5. Educational activities
  6. Religious activities
  7. Public performances, clinics, workshops, athletic and other competitions, and exhibitions
  8. Support for the Cuban people
  9. Humanitarian projects
  10. Activities of private foundations or research or educational institutes
  11. Exportation, importation, or transmission of information or information materials
  12. Certain export transactions that may be considered for authorization under existing regulations and guidelines.

I highlighted #8 because that is the easiest, most straightforward reason to declare for traveling to Cuba. #6 is also a good one if you are religious.

It’s worth noting that this is an ever-changing topic, with American governments introducing different measures each cycle. I will keep this segment updated as needed.

Photo courtesy of ExpertVagabond.com

From the US, the “Illegal” Way

There are those who choose not to get themselves involved in this pissing match, and so choose another option: going through Cancún. I’ve heard of people buying a round-trip ticket from their American city to Cancún, Mexico and then buying a separate ticket from Cancún to Havana. Thus, to the American government, it just looks like you were in Mexico that whole time. I’ve never heard of those people that have done this getting caught.

Pro Tip: I’ve heard that if you go this route, you want to be sure to not get your passport stamped in Cuba. Just request that the customs official not stamp your passport when you get to the counter. You can say “Por favor, no sella el pasaporte.” I heard that they’re totally understanding of this and won’t cause any fuss.


Cuban money can seem a little confusing at first. See, they use two currencies: the peso (CUP) and the peso convertible (CUC). As an American, or any other non-Cuban national, you only need to worry about the latter, CUC (pronounced “kook”). If you’re exchanging money in a bank or going to a mainstream restaurant or museum, it’s all going to be in CUC, which is pegged in value to the US dollar.

Some CUCs
Some CUPs

If, for example, you go into a local convenience store, you might pay with CUC but get CUP in change. The CUP is 25:1 with the US dollar. The prices match up anyway, so it’s not like you want one over the other.

Interesting Fact: It’s technically “illegal” for an American to possess CUP, but it’s not like there’s a cop on every corner checking the coins in your pocket.

It’s worth mentioning that as of December 2019, Cuba was making strides to unite both currencies.

Credit/Debit Cards

I would treat Cuba like a cash economy. The vast majority of transactions are handled in cash. American-issued credit and debit cards categorically do NOT work. Other foreign credit and debit cards, even Canadian, do work on the island, especially in the higher-end hotels. However, ATMs are not plentiful.

Exchanging Money

US dollars don’t have a very good exchange rate because of a 10% fee levied by the banks. So what you should do is exchange your dollars into euros or pounds at your home bank. Then, when you get to Cuba, exchange that money into Cuban pesos. You can exchange some at kiosks outside the airport, but keep most of it for an actual bank, as you’ll get a better rate. I would recommend going to a larger bank branch, like the one at the FOCSA Building, because if you go to a smaller branch it’s a little confusing. Just trust me on this one.



For most travelers, their Cuban experience begins and ends in Havana, and that’s perfectly fine! This blog is aimed at those with tighter schedules, and you can for sure enjoy Havana in a week or even less.

Havana is one of the largest and oldest cities in the Caribbean and offers a lot to do. You have the well-preserved Old Havana; the Malecon, a famous seawall and popular hangout spot; various gorgeous beaches; the Morro fortress; and a very active nightlife scene.

I’ll be posting a separate article focusing on Havana in the near future.

Viñales Valley

If you prefer nature to city, be sure to get out the Viñales Valley. The Viñales Valley is a UNESCO World Heritage Site, notable for its mountains and natural beauty. It’s not far from Havana; you can easily hire a taxi to take you there for about 25 CUC per person.


The central Cuban town of Trinidad is another UNESCO World Heritage Site, and has been called “the most beautiful town in Cuba.”

The Cuban People

Me with Carlos, aka “Chiki,” a dude from the neighborhood

I’m very careful not to generalize any group of people, but there are a few things that cultures all over the world might have in common. I include this section only to give you an idea of the folks you’ll be visiting.

I should also mention that I myself am half-Cuban.

Cuban people, generally speaking, tend to run on the extrovert end of the spectrum. You will find a higher ratio of people who might be described as “in your face” or “very forward.” If you’re haggling with a taxi driver and he thinks your offer is too low, he’ll let you know. If you’re speaking with a dude and he doesn’t think your Spanish is very good, he’ll let you know.

I wouldn’t call this rude, though. In their culture, it’s just more acceptable to let your emotions run very close to the surface. You could be walking through La Plaza Vieja and hear old men shouting at each other on a bench. If you understand some Spanish, you’ll discover that they’re just talking about baseball.

Me with Mirella, owner of the Mirella Hostel in Havana, Cuba

Attitudes Toward Americans

My blog is primarily directed at Americans, so readers from other nations can disregard this part.

Cuba and the US have an interesting relationship. This goes back to the Cuban Missile Crisis of 1962, during the height of the Cold War. Basically, the US was (and is) highly anti-communist, and so embargoed Cuba as a result of Cuban leader Fidel Castro’s communist stance. Blocked off from trade with the US, Castro sought the help of the Soviet Union, who did send them vehicles, food, and supplies…on the condition that they also send nuclear warheads. This was helpful to the Cuban people, but also brought tensions with the US to a boiling point. The other side of my family includes people who stationed in American submarines just off the coast of Havana.

Random Side Note: I love that we call it the “Cold War.” I guess the Korean War, the Vietnam War, and the countless US-backed, anti-Communist governments around the world qualify as “cold.” Anyway…

This has lead some American to mistakenly believe that Cubans don’t like Americans. Yes, you may come across plaques and billboards that don’t seem super friendly to the US.

“What the Imperialists can’t forgive is us making a socialist revolution right under the nose of the United States!” From a speech by Fidel Castro.
“Blockade: The Biggest Genocide in History.”
Um…about that…

But I was there almost a week and felt absolutely zero open hostility. The Cuban people–like people all over the world–are focused on doing their own thing. They have their own lives to live. In fact, I feel like they do a pretty good job of making a distinction between the US government and the US people. If anything, I feel like a lot of Americans can learn something from this distinction.

The Reality

Having said that…Cuba is a poor country, and they do share certain aspects of other poor countries. If you are an American, they’re going to think you have money. Simple as that. It doesn’t matter how much you tone down your attire, they’re going to make the assumption. However, Cuba is also a very safe country, and so you don’t stand much risk of getting mugged. They’ll just try to get your money in other ways, for example…

“Come meet my cousin.”

If you are a young man traveling alone or with other dudes, some local dude is going to offer you a prostitute. It’s going to happen. A dude with a guitar may come up to you at the Malecon and act friendly, maybe play some American pop song, and then introduce you to his female “cousin.” You can bet your last CUC that she’s not his cousin. Or you can be chatting with some neighborhood dudes outside your hostel when a local girl comes up to join the group. You get to talking with her, perfectly amicably, and then you turn around and one of the dudes hands you a condom.

I want to be very clear: I’m not saying NOT to engage with the Cuban people. By all means, one of the best things about travel is making connections with others from around the globe. Even if they do offer you something you’re not interested in, you can still be friendly and make conversation, while being very clear in your intentions. Eventually, they’ll get the hint and they’ll quit pushing it, or move on to the next mark.

The Food

Photo courtesy of FoodRepublic.com

Travelers are very divided on Cuban food: some swear by ropa vieja, while others recommend bringing some tabasco sauce, salt, anything with you to give the food some flavor.

I grew up eating Cuban food cooked by my grandparents, and what I had in Cuba was not that. The Cuban food I had in Versailles in Miami was ten times better than what I had actually in Cuba. Whether this is due to the embargo blocking the import of spices that aren’t strictly necessary is not for me to say.

However, there are exceptions to every rule in the book, and you can find good food in Cuba. I will single out El Biky in Havana for having some of the tastiest pizza I’ve ever eaten in my life.

In general, Cuban cuisine is going to use a lot of rice, beans, pork, avocado, and plantains.

Some general Cuban dishes are:

  • Moros y cristianos: Literally “Moors and Christians,” this is black beans and white rice (hey, I didn’t come up with it). This is a pretty standard Cuban filler, although you can also get the black beans in a potaje poured over the rice.
  • Ropa vieja: Literally “old clothes,” ostensibly because the shredded beef resembles tattered clothing.
  • Masas de cerdo: Pork chunks!
  • Bistec empanizado: Breaded steak, what some of us might call “country-fried steak.”
  • Sandwich cubano: Aka just a cubano, this is going to be a ham and cheese sandwich with mustard and a pickle, on toasted French bread. Some places put pork chunks in place of the ham, although it’s best when they combine the two. This is one of the consistently delicious things you can get in Cuba. Interesting Fact: This sandwich actually originated in Florida.
  • Medianoche: “Midnight,” ostensibly because this is a snack you make yourself when you get up in the middle of the night. FoodRepublic.com referred to it as “the cubano’s hot sister,” which makes me laugh and is kinda true. It is indeed almost identical to the cubano, except the medianoche is flatter.
  • Platanos fritos: Plantains, sliced, fried, and squished flat. Served best with some salt.
  • Avocados: The Cuban way is to drizzle them with olive oil and add some salt.

Note: Good luck finding vegetarian or vegan options in Cuba.

Ropa vieja

What NOT to Do in Cuba


Seriously, you’ll get 30 years for that. They do not mess around with drug use or drug smuggling. Not even kinda.

Random Fact

It is next to impossible to find cigarette lighters in Havana. Like, literally all over the entire city. Why? I have no idea. Your best bet is to look for dudes at desks in alleyways. These are typically entrepreneurs repairing things or refilling Bic lighters.

In Conclusion

Cuba is, if nothing else, interesting and different. Whether you come for the gorgeous beaches or the fun nightlife or just to be somewhere different, Cuba is going to have something for you.

Is there anything I left out? Let me know in the comments below!

Downtown Havana as seen from El Morro

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