Debunking 9 assumptions I had about visiting Cuba as a U.S. Citizen

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Is Cuba safe for Americans? Is it nice? Is it even worth visiting? Do Cubans event want Americans to visit? What is modern Cuba actually like?

One of my favorite travel habits is Assumptions vs Reality journaling. I write down (without judgement) any assumptions or expectations I have about a destination, culture, or people before a trip. I reflect on the journal entry later after I’ve actually been there and formed an opinion. The exercise always shows me the way we all have unconscious biases and can be so wrong about people and places until we go see them ourselves.

Before I did this exercise for my trip to Cuba I didn’t realize I was brimming with preconceptions! Fueled by American history classes, stories of Cuban-American immigrants to the U.S., social media, and general lack of knowledge.

Are you interested in traveling to Cuba, but have some of the same assumptions? Let’s debunk them together! Here's how my assumptions stacked up against the reality on my recent trip with Intrepid Travel. 

It's really difficult for Americans to get a visa to visit Cuba.

Assumption:

“How hard is it to get a visa to Cuba?” is a top Google search for the country for a reason. I don't know why, but I think we've all heard getting a visa is difficult, rare, and somewhat shady process for Americans.

I think it's somehow tied to this “air of mystery” Americans have for Cuba in general (myself included! Which is why I'm making this post!)

Reality:

The answer is, no, it's not. I bought a little pink piece of paper right before literally getting on my flight to Cuba at the gate. It was $60, and as simple and them checking my passport and swiping my credit card.

I also got a lot of questions wondering if travel to Cuba will affect travel to other countries, and if a Cuba stamp in your passport is like a huge, glaring red flag. Luckily, he reality is that your passport isn't stamped at all. They stamp your boarding pass, and Cuban visa which you must keep until you leave the country. Tourists would have a huge issue visiting Cuba at alll if this were the case, so don't worry!

However, I recommend going to Cuba on a group trip with Intrepid Travel for this reason. For Americans to visit Cuba we need to be “Supporting the Cuban People” (technically, it's not allowed for American citizens to visit Cuba for pure leisure). On a group trip, it's already clearly organized and set itinerary, and they can assist you with applying for and organizing your visa because you'll be a part of an educational tour.

This Reddit post is extremely accurate as far as what to really expect in the process to travel to Cuba for Americans. But summary: it's not as complicated or scary as we think.

Cuba isn’t really worth visiting because it’s so similar to Puerto Rico and the Dominican Republic.

Assumption:

Cuba often gets lumped together with other Caribbean destinations like Puerto Rico and the Dominican Republic. Because Americans have unique regulations to visiting Cuba because of the U.S. embargo, many Americans might think “Why visit Cuba, when I can visit similar countries nearby?”

While there are cultural and geographical similarities, Cuba's sheer size took me by surprise. It's much bigger than both countries combined, offering a diverse landscape that keeps unfolding as you travel across the island.

The Reality:

Indeed, I saw certain similarities in Caribbean features between Cuba its neighbors, having been to other Caribbean destinations like Puerto Rico, Jamaica, and the British Virgin Islands in recent years.

But Cuba’s sheer size—10x as big as Jamaica, and 4x bigger than Puerto Rico!— allows it a lot more room to blend urban experiences, mountainous terrain, and picturesque beaches. To me, Cuba's diversity extended beyond the typical Caribbean blueprint.

Cuban beaches are rocky and not worth visiting

Assumption:

Before my visit, I pictured Cuba's beaches as rocky, somewhat unwelcoming shores. I’d heard this in passing from other travelers who told me not to visit Cuba if I was looking for stereotypically Caribbean white sand beaches or luxury.

Reality Check

A lot of Cuba does have rocky shores. Because of the lack of infrastructure, Cuba hasn’t been able to widely invest in aesthetic beaches like it’s neighbors. But just because they’re not Sandals resorts on every corner doesn’t mean there aren’t beautiful Cuban beaches.

Trinidad’s soft, sandy beach Playa Ancon, took my breath away. A true slice of paradise that debunked every rocky beach stereotype I had with soft sand, a stunning sunsets, and abundant cabanas and island cocktails for less than $1.00 USD a pop. 

Even the Cuba’s rocky beaches reminded me of some of the best swimming spots in Turkiye—

Cuban food is bland (and bad)

Assumption

This was the most common assumption said to me when I asked around which was a shock to me! “I heard the food has no flavor”, “The food is bad”, “The food isn't good” were the only comments I heard before my trip.

Reality Check

Firstly, Cuban is limited in the food that's available to them through importation. This can effect availability of ingredients, restaurant s that can open, and what can be served, obviously.

That said, I personally enjoyed Cuban food! I found it similar to Jamaican food with red beans and rice, yuca (cassava), and plantain as a staple for every meal. Maybe that's why I liked it—because it felt like a familiar, filling, home-cooked meal. On the trip we learned the country was full of eco-farms and many of our meals were at farm-to-table restaurants. I'm a huge seafood fan so I also really enjoy how much I found in the Cuban palette! I've never had so much lobster—lobster ceviche, lobster sushi, grilled lobster… I was in heaven!

That being said, I agree that Cuba is not a mecca of culinary innovation, layered spice, or bold flavors—it was one of fresh vegetables and simple, hearty meals.

Cuban Spanish is more difficult to understand than other dialects

Assumption:

I braced myself for a challenging linguistic experience, expecting Cuban Spanish to be hard to comprehend.

Reality:

To my relief, I found Cuban Spanish to be quite clear and understandable. If you know Spanish basics, the language barrier will hardly a barrier at all. Knowing Spanish is absolutely an advantage in Cuba and will open up the country and it's people for more profound connections with locals.

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Cubans are disconnected from the world

Assumption:

Media often paints Cuba as a disconnected place stuck in time. We see images of classic cars, 1950’s design themes in hotels and architecture such as Hotel Nacionel and El Floridita (well known as Ernest Hemingway’s favorite bar!).

In modern times we hear about the lack of job opportunity in Cuba and how visitors have no wifi-connection and tend to disappear off of social media while in Cuba.

Where do they go? What are they doing? This air of mystery Cuba tends to have made me, and many others, assume it would be a land lost to time….

Reality:

It's wrong, but it's also complicated.

In 2024, it’s not uncommon for major hotels in Havana to have wifi. You can buy a SIM card at the Havana airport when you land, and eSIM services like Airalo work fine in Cuba. On my wifi was available in our accomodations. It’s not free wifi like in the U.S.: you need a SIM card or Wifi Card to access it. And it wasn’t always very strong. But it available if you could pay for it!

This is the real dilemma for Cubans: paying for it. Our local Cuban guide told us that the average Cuban might make something around $15 USD per month working a standard job (Cuba has a centralized socialist economy). 1GB of data while in Cuba cost $15 USD.

While internet and media are not regularly accessible to all Cubans, the assumption that the country is a “stuck in the 1950’s” isn’t true at all. Many of the Cubans my age (in their 20’s) had Instagram accounts, are obsessed with streaming the latest Cuban songs, and seemed pretty in tune with news and social media. Almost all older Cubans are keenly tuned into the latest American politics becaus it affects their lives so much.

Tourists are watched under a microscope while in Cuba

Assumption:

Because Americans know Cuba to have a socialist economy, I think most Americans imagine even modern Cuban society as something similar to George Orwell's 1984— with “Big Brother” watching everyone's every move and the average person's life being extremely stressful because of the government's presence.

Reality:

I don’t speak for the Cuban people’s experience because it’s impossible to truly know unless you live there recently—especially as Cuba has changed so much in the last 50 years, and in more resent years due to the pandemic.

But as a tourist I can say that “Big Brother” was far from my experience. In fact, I found Cuba to be have a lot less obvious police presence than most cities in the United States. I saw a lot of security guards, but almost no police on patrol and certainly not harassing tourists or watching our every move.

Businesses, even small private businesses, are regulated by the Cuban government. But the average Cuban citizen seemed able to share their views on their government in Cuban Society somewhat freely in casual conversation.

Cuban’s hate Americans, and don’t want to see American tourists.

Assumption:

To be fair, many countries have a valid right to have negative feelings toward the United States for centuries of cimperialism in the America’s. I thought Cuba no different, especially after learning more about the very active embargo. Americans definitely fear that we are ethically unwanted visitors.

Reality:

The reality I saw during my 2024 trip to Cuba this was not the case, in a truly surprising way.

Because of Cuba’s economic state, any tourist is a good tourist. I encountered tourists from Canada, Brazil, Colombia, Peru, Vietnam, Mexico, and more. Tourists from the U.S. are treated the same as the rest. Because of the hardships of Cuban life, many Cubans dream of coming to the U.S. for opportunity, so for that reason they were curious about us and our lives.

I also tried to find the opinion of specifically younger Cubans—waiters, students, friends I met at dinner. I think most Cubans seem to have a clear separation of the American governments actions and the opinions and beliefs of American people.

Huge New Year's Eve fiestas!

Assumption:

I assumed all Caribbean countries had massive New Year's Eve celebrations. Fireworks, parties, fun—I especially know Cubans for their influence in reggaeton so I assumed there'd be huge parties surrounding music, dance, and ron!

Reality:

Cut the fireworks and salsa music. Cuban New Year's Eve turned out to be a heartwarmingingly intimate event.

Instead of grand parties, families gather to celebrate in a more personal, communal way. I found Cuban New Year's Eve to be surrounded by ritual and some very interesting traditions. We celebrated in Cienfuegos. The locals explained to us that in this region there are 3 main traditions: tossing a bucket of water out of your house into the street, burning a life-sized doll in the middle of the street (to represent saying goodbye/cleansing the past year), dancing around it and singing.

On my trip, the locals welcomed us into their celebrations without hesistation and we danced around the fires with a group of local kids singing, and salsaing.

There was some ron involved, but the night was more wholesome, calm, and beautiful than I imagined.

My journey through Cuba was an eye-opening experience, challenging my assumptions and replacing them with a nuanced understanding of this beautiful country. Cuba is a land of contrasts and surprises, rich in history and culture, far different from what many of us have been led to believe. It's a reminder of how travel can broaden our horizons, shatter stereotypes, and connect us more deeply with the diverse world we live in.

Did you have any of these assumptions too? Did this blog post help you? Are there any questions I can answer as an American tourist who has recently visited Cuba? Ask them in the comments below, I'll respond there!