How to Travel to Cuba as an American

Cuba Appreciation Post and how to get YOU there.

People are a little confused on the whole Cuba thing. Are we allowed to go or are we not? Obama opened the gates for tourism and then Trump closed them (or at least made it a little more difficult) again. But the answer is YES. Absolutely YES you are legally allowed to go to Cuba and I highly H-I-G-H-L-Y recommend it.

Support The Cuban People

On top of the beaches, history, architecture, cheap prices, rum, and tobacco you are contributing to a country desperately trying to rebuild itself. Life for Cubans is expensive and they are just recently permitted to operate their own restaurants, ice cream shops, and Airbnb style guesthouses. This is called “The Private Sector” and spending money here will give you the best food options, unique guesthouses with knowledgeable hosts, and put money straight into the pockets of Cuban people.

So how do I get there?

Cheapest Option: Fly with a layover in Mexico (or Panama)

This is the way I did Cuba. It’s a great way to explore the country all on your own and pick and choose the exact sights that you want to see. I’m not a huge museum kind of person.  I tend to gravitate more toward the beach (with a pina colada) or anywhere I have a chance to spot exotic animals, while others may be looking for a more food/history centered trip. This route allows you to do WHATEVER you want -stay a week in Havana, stay 2 nights, or skip it all together…the world is your oyster. Don’t completely skip Havana though you’ll seriously regret it. 


You will book the flight like you normally would. You can even book it round-trip and put Cuba in as the destination. Just make sure you stop somewhere along the way. It will likely be a destination like Mexico City or Cancun or even Panama City.

I opted for the LONG layover. We’re talking 20 hours. It’s my new favorite way to travel because it breaks up the long flight and allows you to leave the airport to get a glimpse of a whole new city. It’s like two trips in one (kinda, maybe I’m a little bit of an optimist). Whatever you do just make sure to go to your airlines counter before your last leg to Cuba and purchase a Visa.

Cuban Visas: There are technically 12 categories you can purchase a Visa under ranging from Religious to Support of the Cuban People. The easiest reason to claim as a tourist is the latter. I am eating in their restaurants and buying their goods so technically I’m supporting them, right? 

I was told that going this route I should ask the customs counter in Cuba to NOT stamp my passport but to alternatively stamp my Visa paperwork, which I did. But Evan did not. Either way, no one hassled us or even looked twice at our passports when we were coming back into America. But if you want to be on the safe side just ask them to not stamp it.

No Hassle Option: Guided Tour Group

The most government-approved form of travel in Cuba is through tour groups. They offer a variety of scheduled activities including exploring the tobacco valleys, rum tasting, or museum hopping in Havana. There are tours specifically set up for foodie’s or for the ocean lover who just wants to relax on Havana’s more scenic coastlines. The problem is most tour companies are insanely expensive. I managed to find one site that had a variety of tours for cheap and if you can find one that interests you it’s a great way to see the country while you sit back relax and enjoy the ride.

How they work

They operate under the “people to people” Cuban visa and allow American citizens to contribute directly to the Cuban people. Americans aren’t legally allowed to stay in hotels or eat at restaurants where the money is benefitting the Cuban military so this route ensures that you would be abiding by those rules. You also have the benefit of having a walk around tour guide to fill you in on Cuba’s rich history as well as hopefully the possibility of meeting some new friends in your tour group.  Another major benefit for those with limited vacation flights! Instead of a layover in another country where you have to immigrate and go through customs, you can fly straight to Cuba! It’s only 100 miles off the coast of Florida after all.

Cuba’s Two Currencies

Whatever route you choose you are going to need to be somewhat familiar with Cuban currency. It gets a little confusing because they have two. The Cuban Convertible Peso (CUC) and the Cuban Peso (CUP). The Cuban convertible is most commonly used by tourists and is equal to 1 USD. You will end up dealing in CUC most commonly 1) Because it is the currency you will be given at the airport exchange. 2) Because you will be charged “Tourist Prices” on the island. The Cuban Peso is going to be used to pay for street food and small items like coffee at a local cafe and food from authentic Cuban restaurants. 1USD or 1 CUC is equal to around 25 CUP. So if you don’t learn the difference it’s easy to get ripped off.

A quick way to differentiate between the two… CUC has statues and monuments on it while CUP has faces similar to the United States Dollar.

If you travel with a group from the US odds are that most activities will be paid for in advance. So you won’t have to worry about currency conversion and handling money carefully (as much). But for the backpacker’s out there here’s a few other financial hurdles it’s helpful to know in advance.

Financial Hurdles

  1. Before you arrive in Cuba it is financially beneficial to convert your USD to the Canadian Dollar or Euro’s. THEN convert to CUC on arrival in Cuba. This is because there is a 10% tax taken off the top for any USD exchanged in Cuba.
  2. Consider exchanging to CAD or Euros at a local currency exchange. I use LA Currency and rates are significantly better than what you would get at the bank or airport.
  3. From the moment you get to Cuba make 100% sure that all the money given to you is the correct Cuban currency. It doesn’t happen often but it’s an easy way for people to scam tourists.
  4. BRING ALL THE CASH YOU ARE GOING TO NEED. I cannot emphasize that enough. You will have NO access to banks, credit cards, online money transfers, internet via smartphone, ATM’s of any kind. Cuba is a unique travel destination in that the only money you have will be the cash in your wallet. With that in mind be extra careful where you put it because pick-pocketing does happen on occasion.
  5. My biggest travel tip is to bring 200 USD more than you think you’re going to need. Because let’s face it you’re gonna want cigars, you’re gonna want rum, and there will be nights you want to splurge. It’s nice to have the freedom to pay for a spontaneous adventure when one comes around.

You’re Ready to Plan Your Cuban Vacation!!

Now that you have the inside knowledge on getting to Cuba it’s time to plan your stay! Check out our three-week journey through Cuba if you need a little more inspiration.


Question? Comments? Let me know here!