How to Travel to Cuba as an American

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The common misconception is that we can’t travel to Cuba, and if we can, it won’t be easy.  Yes, there is a system in place that appears strict, which tends to deter people because it’s not worth the headache, but I am telling you now — it couldn’t be easier. Here’s how to do it and what to be mindful of before you arrive. 

Choosing a Category

There are 13 categories you can file under in order to travel to Cuba. You will file under “Support for the Cuban People.” Most people think you have to go with a tour group if you’re going to Cuba and that is true under the “People to People” category, but that’s not what you’re after. 

“Support for the Cuban People” is just that — you’re here for a local experience. You’ll stay in a Casa Particular, which is anything bookable on Airbnb and is just a name for property owned by Cubans (and not by the government / military), and you will shop and eat locally (family-owned restaurants are called Paladares). That’s it. Simple as that. Note: the U.S. government asks you to save your receipts for five years following your visit, so just file them somewhere safe on the very off chance you need them.

Airport Protocol

You're not able to check in for flights to Cuba online, so budget at least 2+ hours to do this at the airport. Typically, there are designated airport lines for travelers headed to Cuba since you need to both check-in and purchase a tourist card. The tourist card, also referred to as a tourist visa, is required of every traveler from any country that visits Cuba. Most airlines offer this for purchase at check-in, and your flight also typically comes with health insurance, which the Cuban government requires from all tourists. To put this into numbers, I flew with jetBlue from JFK and my flight was $290 RT (with included health insurance) and the tourist card was $50.

Now, hold on tightly to this tourist card, guys. You'll need to give half to the immigration officer in Cuba on the way in, and then half on the way out. This is v important! P.S. Cuba does not care about your categories, this is for the U.S. only. So don't sweat the process.

When you return to the states, you'll do everything typical of an international return, they just may ask you your category, length of stay and purpose of trip. All normal!


Now, listen, I’m going to get really real with you for a minute, because there are some serious things you need to know before traveling to Cuba. This is NOT to deter you from taking this trip -- you should, and frankly must, experience this country because it's unlike any place you'll ever know. But I do wish that, in all of the guides and on all of the blogs that I read, someone outlined just what a culture shock it is to be here. Here's what you should know:

This is a communist country. The level of poverty may shock you. It is extremely evident upon arrival that there are wealthy people, most of whom work in the tourism industry, and then there are very, very poor people. People live in desolate buildings and places that are not dissimilar to living outside. Yes, education and health care is free, but that doesn’t mean it makes their lives easier. Many young people can’t seize the opportunity of free education because they have to work to help support the family.

Everyone IS hustling you. Okay, not everyone, but it sure will feel that way, and to the point where you don’t want to get involved in a conversation with a seemingly friendly Cuban because what usually comes next is them trying to sell you something, whether it’s a tour, cigars or rum. This sucks, frankly, because you want to get to know the local culture and feel comfortable in conversation, but trust me when I say that more often and not, they're motivated by your money. A couple of quick examples to look out for: the locals will approach you and tell you there's a special "colectivo" where for one day out of the whole year, the government doesn't regulate cigars or rum so you can buy in bulk and for a very low price. They will tell you that day is today. This does not exist. The "colectivo" you're taken to is literally any unmarked storefront where they can try and sell you things that have been stolen, tampered with, or are not up to code. For this reason and all others, never buy off the street. Ever.

100% of cars on the road are taxis. They will pull over and try to take you somewhere and negotiate a fee. I repeat, literally any random car can and will attempt to pick you up. *Try* not to get into a car that’s not marked with the “taxi” sign. This is for your general safety. If you need to hail a taxi, try to do so from a hotel. If you need to hail from the street, try to wait to raise your hand until you see one approaching your direction. Otherwise, you will get a lot of unwanted attention. Now, there are times where you'll be left with little choice but to get into a car that seems legit but does not have a proper sign if you're in Old Havana. That's OK, but remember, make sure you set a fair price in your head before you enter negotiations and stick to this price. Someone will drive you for it. Promise. 

Foreign women are cats. If you are not with a man, you will be catcalled. And I mean, a lot. I was traveling with my best friend and every block we walked we were subjected to this, both in English and in Spanish. I’m not telling you this to scare you, and honestly you can ignore it after a while, but it’s a serious shock upon arrival that you can avoid if you’re prepared. Don’t let it phase you -- no one will touch you or follow you and there really is little to no crime against tourists here, but words can be jarring and for that, I must warn you.

All of that said, Cuba is an experience unlike any other. You're traveling back in time to the 1950's when cars were fierce and buildings were candy-colored and the streets were filled to the brim with noise and life. You will not regret this trip.

Ready to plan your trip? Check out my 4-day itinerary to Havana, Cuba here.

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Cherry