I’m an American. How do I travel to Cuba?

In a local music venue in Old Havana, we’re stopped by an elderly Cuban man.

“Americans?” he asks.

“Yes,” we reply. Everyone not only seems to know that we’re Americans, but that we’re Californians too.

The man, a professor of history in Havana, wants to talk to us about the history of Cuban-American relations. This is just one of many times my boyfriend and I were stopped on the streets of Havana to be engulfed by stories of Cuba’s revolution, discussions of politics, and conspiracy theories of Che Guevara’s death.

This man, in particular, wanted to apologize for the Cubans’ role in the embargo. Surprised? We were too.

Our travel restrictions, and much of Cuba’s relegation to the technological dark ages, rests on the embargo that President Kennedy placed on Cuba in 1962.

When the Cuban revolution was won, the Castros nationalized all Cuban land. Many poor, landless citizens were given their own land, and a chance at a better life. Fidel Castro also gave them free education and health care that Cubans still enjoy to this day.

But the land that was parsed out to the poor came from wealthy Americans and Cubans (including Castro’s own family). Many American corporations owned Cuban land – a lot of them were sugar plantations that they could operate cheaply in Cuba. When the land was nationalized, many Americans lost a lot of money. We swiftly reacted with the Cuban trade embargo. Over fifty years later, and we still have not loosened this economic stranglehold on our socialist neighbors. This brings us to today, with an elderly Cuban history professor apologizing to a couple of bewildered Americans in Old Havana.

Just because going to Cuba is “frowned upon” doesn’t mean that you can’t do it. And it’s becoming easier every day with travel restrictions slowly unraveling. Here’s how we did it, and how you can do it too:

Do I need any special documentation to enter Cuba as an American?

As recently as 2014, Americans have been technically allowed to travel to Cuba. However, you had to do it under the guidance of a “People to People” tour, through the Office of Foreign Assets Control (OFEC). You could also apply for a travel license given for official purposes such as journalism, research, family, etc. 

Today you don’t even need those guises to get to Cuba. However, you are still required to pretend like you’re going for reasons other than “just because” and “Starbucks doesn’t exist here yet.”

First get your third party country plane ticket. This is the ticket you purchase to throw the scent off of Cuba. Your best and cheapest choices are Mexico and Canada. We chose Dominican Republic, because… reasons.

When we went to the ticketing booth to retrieve our Cuba flight tickets, we were met with what I could only presume to be mild curiosity and amusement at our obvious anxiety. We were certain we would be turned away at any minute.

The ticketing clerk disappeared into the back office, and after a 5 minute wait full of nervous darting glances between the two of us, he came back with a paper that simply asked us to mark down the reason we were going to Cuba.

We chose education. With all there is to learn in Cuba, we’ll just call this a white lie. And since you’re not required to prove that you’re going for “education” or “religious purposes,” we’ll just say that this is ‘Murrica’s sly wink in our direction.

Where do I get my travel visa?

You can get it at the airport of the third party country of your choosing. You MUST get it before you arrive in Cuba. This is something we learned the nerve-wracking way.

We had read in a few places that you could buy your visa once you arrive in Cuba. Not true. We even asked someone at the Santo Domingo airport where we could purchase it, and they also said Cuba. However, my Spanish is not the best so, who knows?

The realization came in line to board the flight. We noticed the flight attendants checking visas and we quickly inquired about the situation. We were told we could not board the flight without a visa. Fortunately, they told us we could buy the visa right at the desk. Unfortunately, we could not pay in Euros, which is all we had on us at the time (I will explain later).

So, as the line of boarding passengers dwindled, and I stood gnawing my fingernails, my super cool boyfriend sprinted a mile across the Panama airport, barefoot, to retrieve cash to board the flight to Havana. We made it right before they closed the gate.

The moral of the story is that you need to buy your Cuban visa in your third party airport, preferably before the flight starts to board. Visas cost $10.

Do I need anything else?

Yes, insurance. But you really can buy that in Cuba before you go through customs.

Cuba will accept other forms of insurance, but if you’re in American you’ll need to buy it there because they don’t recognize American insurance. It costs $4 per day and you need it to enter the country.

Will they stamp my passport?


This one is up for grabs. Technically you’re allowed to be in Cuba for various non-tourist reasons, so they should stamp your passport as a matter of policy. We read that a lot of customs agents will ask if you want your passport stamped, but we didn’t have this experience as we entered the country. Without a word, one customs agent stamped my boyfriend’s passport, and another stamped my visa instead.

On the way back into the States, US customs agents took no notice of my boyfriend’s Cuba stamp. I’m still mildly devastated that my passport doesn’t include a Cuban stamp.

Will my plastic work in Cuba?

Most places in Cuba do not accept cards, but they come in handy if you need to get more cash out of the ATM. However, not all American banks recognize Cuba as an acceptable place to spend your money. My bank was one of them. In cases like this, make sure you bring more than enough money to get by, and then some. You never know when you’re going to need some extra cash.

Unfortunately, Cuban Pesos can’t be exchanged anywhere in the world, so don’t exchange all your money when you get there. Keep the extra cash in your home currency. If you do need to exchange it, there’s plenty of banks that’ll give you a good rate. We were even able to exchange currency at our hostel and Casa.

Also keep in mind that, as an American, exchanging money can be much more expensive because there’s a 10% penalty fee attached to American dollars in Cuba, on top of whatever the exchange rate happens to be at the time. Before we left San Francisco, we actually exchanged our dollars to euros to avoid the 10% penalty fee and save us a couple bucks.

Do Cubans like Americans?


I don’t want to leave you with the impression that all Cubans feel responsible for the trade embargo. I believe this was a unique instance that came with a very interesting history lesson. That being said, this man was one of many who stopped “the Americans” on the street to have a chat, to proudly and kindly share their culture with us.

I think that we’re unique to them, just as they were to us. We’ve been separated from each other and our cultures have grown exclusive without the influence of one on the other. I definitely got the feeling, more than anything else, that our presence there was treated like a strange guest that everyone wanted to poke and prod at – to get at the heart of some fundamental difference, but what we found in the end was a fundamental sameness.

Without fault, we were greeted everywhere by kindness, curiosity, and enthusiasm.

My closing advice is: go now! Cuba is like no other place in the world. A tropical paradise of crumbling colonial buildings, sparkling blue-green water, blatant propaganda, classic cars, and a revolutionary history that still lives and breathes in the soil itself. Go now before it all changes.


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