Traveling to Cuba as an American is very confusing. Can you go? Should you go? We’ve partnered with Keryn Means of Walking On Travels to give us a few tips and answers to get you to this previously forbidden island legally, so you can see what all of the fuss is about.  

Havana Cuba

Photo courtesy of Keryn Means/Walking On Media LLC

Cuba. The land of Castro, mojitos, Hemingway and the crumbling buildings photo dreams are made of. There are also stunning Caribbean beaches, some of the best cigars in the world, delectable rum, and my favorite, pulled pork, rice and beans.

Since the 1960s Cuba has been under a U.S. embargo, which was only recently adjusted to allow some forms of travel under the Obama administration. While many opposed lifting restrictions due to the fact that Castro was still in power and communism is still the reigning political party, it did open the floodgates for U.S. tourism in the market. However, there are a few things Americans traveling to Cuba really need to know before they book a trip, so let’s get started.

Havana Cuba

Photo courtesy of Keryn Means/Walking On Media LLC

You aren’t the only ones there

One of the silliest things I’ve ever heard an American say when they arrived in Cuba is “Oh, look, there are so many Europeans here.” Well, yes. While Americans have been barred from Cuba, the rest of the world has not. Canadians have been going to Cuba for years on their winter holiday, as has the rest of the world. In fact, they are a little miffed we found their hideout.

Cubans speak English

Spanish is the official language of Cuba, but many Cubans, especially those living in the cities and catering to tourists do speak English. They are always excited to chat with you. Some are trying to get you to jump in a vintage car for a paid ride, but others are just curious because Americans are finally showing up.

Havana Cuba

Photo courtesy of Keryn Means/Walking On Media LLC

How to legally travel to Cuba

Cuba is still under the U.S. embargo, meaning you can’t just go to Cuba to sit on the beach. You still have to fall under one of the 12 categories of the Cuba travel affidavit. Most casual travelers will fall under “people-to-people travel.” This can be with a pre-arranged tour group or a self-guided tour.

Tour groups are pretty easy to justify with the government. The tour company is going to make sure you fulfill all of your personal interactions that the U.S. requires under the travel affidavit. It’s the self-guided tour that you have to watch out for and be mindful of before you go.

You will need to keep a journal of your activities on a self-guided tour of Cuba. You are required to spend six hours or more talking to and interacting with Cuban nationals under the “people-to-people” self-guided tour option. This could mean talking about Cuban art with the local bartender in Havana. However, the U.S. government would never make it that easy. You need to have a receipt to prove you had that drink. Then you must write down the bartender’s name, what you talked about, when you where there. You are expected to keep a journal of your activities and hold onto that journal for at least five years.

Be mindful as you post on social media as well. If you are showing off too much free time alone, without interacting with the locals, this could bite you in the bum later on. Who knows how closely the government is monitoring these trips to Cuba. It is always better to be safe than sorry.

Havana Cuba

Photo courtesy of Keryn Means/Walking On Media LLC

Getting to Cuba

Many major airlines, including Southwest, American Air, Delta, United, Alaska Airlines, Frontier Airlines, Spirit Airlines and jetBlue, now fly to Havana. Several American-based cruise lines are also getting cruise port access to Havana, Cienfuegos, Santiago de Cuba and other ports of call around the island so passengers can get a better taste of Cuban life (at least for a few hours).

Once you are on the ground, taxis are plentiful (yes, you can hire a classic car with a personal driver) or you can rent a car from one of the state-owned agencies. The bus system and trains do run, but they can be slow. It’s a great way to get that people-to-people interaction though.

traveling to cuba

Photo courtesy of Keryn Means/Walking On Media LLC


Probably the most confusing thing for Americans is the currency of Cuba. They have two. One is for the tourists (CUCs) and the other is for nationals (CUFs). No American dollars are accepted. You cannot exchange your money in the U.S. You must exchange it once you get to Cuba. The exchange rate isn’t great. There is a fee to exchange, but you got to go to Cuba, so you deal with it. Food and drinks are cheap, so you will come out on top in the end.

Overall, travel to Cuba for Americans has gotten easier. However, there are still some hurtles you have to overcome, especially if you want to book your own trip. Hotels are booking up months in advance thanks to American tour operators. Not everyone is sure if they can go to the beach. By the way, you really can’t. (Not unless you want to volunteer all day at a school or with an NGO.)

Do your research. If you decide to venture outside of Havana, I’d advise sticking to the authorized purpose of your Cuba trip, to be safe. There is plenty of art, history and culture to explore. You will have more than enough to fill your journal and get that people-to-people interaction you need.

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