How to Travel to Cuba as an American (like I did!)

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Americans are banned from visiting Cuba as tourists, but don’t be deterred – you can still visit Cuba as a US citizen!

All of the Caribbean is open for American travel… except for Cuba.

Cuba is only 90 miles from Florida as the bird flies. From Key West to Havana, the distance grows a bit longer at 260 miles, which is just about the same distance as Houston from Dallas. Despite this proximity, Americans have been banned from visiting Cuba since 1963. There was a brief stint during the Obama administration where the restrictions were greatly reduced but the Trump administration re-instated them. The Biden administration has not meaningfully changed the policies.

However, do not be deterred! I visited Cuba in May 2023 and had a wonderful time. Find out how Americans can travel to Cuba, despite the current outdated political policies!

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Why can’t Americans freely go to Cuba?

Because of a 61 years-long grudge.

The United States imposed an embargo against Cuba due to their dealings with the Soviets, which began in 1958 with an embargo on the sale of arms to Cuba. The sanctions stepped up over the next 4 years when the Cuban Missile Crisis of 1962 lead JFK to take further steps, including banning Americans from visiting Cuba.

President Obama started to “thaw” these frosty relations and began moving to reestablish diplomatic relations in 2014. Their status as a state sponsor of terrorism was rescinded and the ability to transact with Cuban entities began to get easier.

However, once President Trump was in office, he tightened up the restrictions that were loosened during Obama’s tenure. The Biden administration has loosened some regulations but we have not returned to the openness from the Obama administration.

Despite having present, modern-day enemies of the state much more severe than Cuba, the US government only restricts travel to Cuba that I’m aware of. Despite Level 4 – Do No Travel advisories for Russia, North Korea, and Venezuela, the US government doesn’t prohibit citizens from visiting. Any travel restrictions on American passports are imposed by the other nation, not the US.

In fact, despite the travel restrictions, Cuba only has a Level 2 – Exercise Increased Caution advisory! (as of August 2023).

Tourism to Cuba is explicitly forbidden. You are able to visit Cuba under 12 recognized categories, however.

The 12 categories of authorized travel to Cuba as an American

As mentioned above, visiting Cuba for tourism is banned under the Office of Foreign Assets Control (OFAC). However, you are permitted to visit under one of the below purposes:

  1. Family visits
  2. Official business of the U.S. government, foreign governments, and certain intergovernmental organizations
  3. Journalistic activity
  4. Professional research and professional meetings
  5. Educational activities
  6. Religious activities
  7. Public performances, clinics, workshops, athletic and other competitions, and exhibitions
  8. Support for the Cuban people
  9. Humanitarian projects
  10. Activities of private foundations or research or educational institutes
  11. Exportation, importation, or transmission of information or informational materials
  12. Certain authorized export transactions

I visited under the 8th category: Support for the Cuban People.

American restrictions once you’re in Cuba

American credit cards & debit cards do not work in Cuba. Not at all. Not anywhere.

This means you can only transact in cash. You absolutely must bring at least as much cash as you expect to need and exchange it to Cuban Pesos upon arrival. Many Cubans will accept USD, as long as the bills are in excellent condition (not ripped/torn/damaged).

Cell phones can be hit or miss. I often travel with the $10/day Verizon “Travel Plan” package but either did not attempt it in Cuba or it did not work.

How to visit Cuba under “Support for the Cuban People” (like me!)

My trip was organized by Here and Now Travel, a boutique travel group for 21-35 year olds. You pay the trip cost and they plan everything else! I loved Here and Now, but there are other travel companies available with trips under this category that you can choose from if need be.

Believe it or not, the Code of Federal Regulations (CFRs) outline what constitutes “Support for the Cuban People”. Read the CFRs for all the details, but long story short, your trip must meet the following requirements:

  • Engage in a full-time schedule that enhances contact and support with the Cuban people
  • Results in meaningful interactions with Cubans
  • Does not violate any financial or lodging restrictions

This does not mean you just get to go as a tourist! You can be subpoenaed by the OFAC which can result in a warning, your Global Entry being rescinded, or even severe fines.

Casa particulars seem to be the safest way to not violate the lodging restriction. A casa particular is basically a homestay with a Cuban – in my experience, it was like a mix of a hostel and a bed & breakfast.

For my trip, we stayed in a casa particular, had a Cuban local as a dedicated tour guide, had a Cuban local as a dedicated driver, and went on specific day trips where we interacted with and learned from Cuban locals. Every day was jam-packed and each adventure was an opportunity to learn more about Cubans and their individual stories and challenges.

The OFAC can request information from you about your trip for up to 5 years after your return. This is serious business!

Side rant – I see so many Facebook groups where people recommend you just travel under “Support for the Cuban People” and plan on being a tourist. “What are the odds the government will audit me? How would they even know?”

Y’all. It’s in the Code of Federal Regulations!

If you want to visit Cuba, do it right. Understand the regulations. Follow the regulations. Why would you risk it?

How departing for Cuba works

I flew direct from Houston’s Bush airport (IAH) to Havana (HAV) on United. Your experience may be different, so check out what your specific airline and airport offer.

Flights to Cuba had a separate check-in location from all other United check-ins. I first paid for my Visa (~$80 ish) and then checked in. When I could demonstrate that all my documents were good to go, I got a Cuba travel-ready sticker on my boarding pass.

You can pre-order your visa, so if you are uncertain if the airport offers Cuban visas, definitely do that!

After that, boarding was easy!

I was not able to keep my boarding pass – I cannot recall if United took it or if Cuban customs did, but you will not be able to keep it regardless.

Important to note! Your purpose of travel is very much an American regulation thing. When entering Cuba, you may be asked the purpose of your visit. Unless it’s official business, say “tourism”. Saying “support for the Cuban people” will confuse them.

How re-entering the US from Cuba works

The flight back to the US was easy. Again, I was not able to keep my boarding pass but they also took my tourist card (Visa) prior to departure.

When going through US border control, I did not get grilled. The guy checked out my passport and that was that. My other travel companions did not have as easy of a time.

One of my companions had Global Entry, like me, but when he was asked “how did you specifically support the Cuban people?”, he totally froze. The CBP agent threatened to rescind his Global Entry on the spot.

Moral of the story? Be prepared to answer how you supported the Cuban people!

After that, I was back stateside. Easy peasy!

Can I bring back Cuban rum or Cuban cigars?

Nope! You are allowed to consume Cuban rum and Cuban cigars while in Cuba, but you are forbidden from importing them. I’m not sure what happens if you’re caught… so don’t risk it!

Is travel to Cuba safe? Are Americans safe in Cuba?

Absolutely! I never felt at risk while in Cuba. I was in a travel group, however, which of course helps.

Cuba has a Level 2 – Exercise Increased Caution advisory so it is not without risk… but other Level 2 countries include France, Germany, the UK, and somehow even Antarctica. This means the government views the risk of visiting Cuba as about equal as the risk of visiting these other Level 2 nations.

Cuba is a poor country, so as long as you are secure with your belongings and don’t flash a whole bunch of cash, you should be fine.

Was visiting Cuba worth it?

100%. I adored my time in Cuba. The people were so nice, the food (and drinks) were divine, but most of all I loved understanding the Cuban-American relationship from a Cuban’s perspective. To be frank, I knew just about nothing about Cuba prior to visiting. I knew there was the Cuban Missile Crisis, something about Guantanamo, and that Ernest Hemingway enjoyed Havana. I didn’t learn everything there is to know about Cuba on my trip but it lit up my curiosity and I find myself continuing to read more and more about these historical events.

American travel to Cuba is restricted, not forbidden. Follow the requirements to experience this lovely island!

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