Americans Traveling to Cuba Illegally

It seems that over the past few years, Cuba has become a hot spot destination for travelers from all over the world. It could be the allure of the country’s colorful classic cars, the old school architecture or it’s vibrant Latin culture; whatever the draw is, Cuba is hot right now! But despite it’s boom on social media and travel blogs, Cuba still remains a grey area for Americans in terms of legality.

Restrictions on travel to Cuba is a confusing subject matter that changes faster than you can say cuba libre

Disclaimer: We’re travelers, not lawyers. Always be sure to do additional research and consult with a travel agent or lawyer if you’re unsure about your legal status as an American traveling to Cuba.

Is it illegal for Americans to go to Cuba?

In a word – yes. It has been an everchanging restriction since Obama took office in the US and started easing up on restrictions for visiting Cuba. Obama allowed 12 legal categories for travel to Cuba. One of these, called “people to people” trips, granted special visas to groups like school groups, choirs, religious orgs, etc. This is how Jay-Z and Beyonce famously visited Cuba legally. They went with a museum foundation and their trip was tailored to meet certain education requirements.

Since Trump has taken office he has putting the restrictions back into place. In June 2019, Trump banned US-based cruise companies from docking in Cuban ports. As recently as October 2019, Trump has restricted flights from the US to any Cuban city except Havana. His administration is also eliminating people to people trips. As of October 2019, 11 of the legal categories of travel are still in effect. This includes family visits, professional research, school trips, journalism, athletic competitions and other organized trips. 

The most popular, and perhaps most ambiguous, is the “support of Cuban people” license. You don’t need to actually apply for one of these categories, they’re simply guidelines to better understand whether your trip is technically legal or not. When you travel under one of these categories, you’re supposed to only be traveling to Cuba for that specific reason. Any tourist activities that fall outside that category (ie. sightseeing, beach hopping) are not allowed. 

Click here! A Must Read For All Americans!

How to Legally Travel to Cuba as an American

But can’t you be fined thousands of dollars and get thrown into jail?

Technically you could face a $250,000 fine and 10 years in jail for violating the law. Okay, that’s enough to make anyone sweat during customs, but in reality the law is rarely enforced. Obviously if you plan on going illegally through Mexico, you have to take this at your own risk. 




But won’t I have a Cuban stamp in my passport?

Not necessarily, but it is possible. When you arrive in Cuba (and this goes for everyone, not just Americans) the customs officer can stamp a small piece of paper and staple it into your passport. When you leave they simply take it out and your passport is clear of all Cuban evidence.

The only catch is that when you return to Mexico, or wherever you flew from, you will now have two entry stamps in your passport from that country. If you are super paranoid, I’ve heard of people asking the customs official to not re-stamp your passport, but I think that’s a bit over the top. When you get back to the States immigration would have to examine your passport, check each stamp and compare dates. And let’s face it, they don’t really care that much.

Also, even if you do get your passport stamped, because Cuba travel is becoming more legalized it really isn’t an issue. On our second trip to Cuba in 2016 I actually got my passport stamped on the way through to the US… immigration didn’t even bat an eyelid. Read more about it by clicking our How to Legally Travel to Cuba as an American graphic above.

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How Does the Money Work?

Unsurprisingly, the US government has a block on any US debit and credit cards, so don’t show up with just your MasterCard or Visa.  We traveled from Cancun to Cuba, so before leaving I withdrew a large amount of Mexican pesos and exchanged them in Havana. The exchange rate is decent, but Euros, Pounds or Canadian dollars are better. You can bring American money, but they tack on an extra 10% charge when exchanging American dollars, so it works out at a terrible rate.




Can you fly from the US to Cuba?

Unfortunately, buying flights to Cuba is not as easy now that the US has started to increase their restrictions for travel. You can still buy tickets, but non-stop tickets are rare. 

Cuba Flight Booking Guide

How to Book Cheap Flights for Cuba Travel

Do Cubans Like Americans?

Cuba & the US have a rocky history, and a shaky present for that matter. The history is long and complicated (for a quick summary I suggest Wikipedia) and I won’t get into my personal views on our diplomatic relations in Cuba, but I can tell you from personal experience that Americans usually feel very welcome in Cuba. Locals are very interested to hear about life in the States and it’s unlikely you’ll feel prejudice for being American. And the bottom line is that American tourists bring in money, so they welcome us with open arms.


Internet Censorship in Cuba

One thing that is difficult about traveling to Cuba is not only accessing the Internet, but also being able to access your content and data securely and unrestricted. According to Reporters Without Borders, Cuba has some of the tightest Internet restrictions and censorship around the world, particularly for the local population. During our time in Cuba we didn’t experience too many instances where our Internet was restricted, but we were heavily concerned about the use and security of our private data that is heavily monitored by the Cuban government. To bypass any potential censorship issues, and concerns about data security and privacy, we always ensure we have a good VPN service to help bypass Internet censorship and ensure safe data encryption when accessing private information like online banking and social media accounts. We’d recommend a company like ExpressVPN for helping you get set up with a simple VPN service to ensure your data stays your own when visiting Cuba.




But isn’t Cuba an oppressive communist country ran by a tyrannical dictator and aren’t you a traitor to America for traveling there??

Well, I suppose this is a personal decision you have to make before traveling to Cuba. I won’t speak of the pros and cons of a communist state but I will say that many friends and other travel bloggers absolutely love Cuba. The people are incredibly friendly, many people safer there than anywhere in Central America, and it would be a loss to avoid Cuba only because of the biased stereotypes depicted in American media.

Side Note: For the sake of clarity in my writing and making this article easy to search in Google I have used the term “American” to reference US travelers. Cuba is, of course, part of the Americas and I apologize if I have offended anyone by limiting this term.

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44 thoughts on “Americans Traveling to Cuba Illegally”

  1. My husband knows someone who is supposed to travel to Cuba to attend a destination wedding (yes, seriously) and they’re in the process of trying to figure out all the logistics. Have no idea if it’s different for non-Americans, if it’s any easier or harder.

    • The US government is the only one that bans its citizens from traveling to Cuba (as far as I know) So as long as he isn’t American, he should be okay! We’re just the unlucky ones. Wow, a destination wedding in Cuba sounds amazing! There are plenty of gorgeous, romantic locations that would make a great venue.

  2. Hi Christine,
    Great article on travelling to Cuba. We are thinking about a mid-March, 8 day trip to Havana. How available are flights from Cancun if you just show up without a reservation? or, should we buy tickets online?(a little paranoid about leaving a paper trail)

    • Hi Richard,
      Glad you liked the article. We bought our tickets from the office, the day before our flight and didn’t have any problem. You can go on the Cubana site and keep an eye on the flights, or better yet, give their Cancun office a call and ask how many seats are available on upcoming flights. We felt safer doing it this way than buying online. Good luck and have fun in Cuba! Let us know how your trips goes when you get back!

  3. This is such an informative post. I have never really looked into going to Cuba because it seemed like it would be a pain. But you have now done all the research for me! 🙂

    I am now going to read every post you made from Cuba!

  4. Really helpful article. Did you pay for hotels with cash too? Usually they require a credit card.

  5. For a long time I thought it was all countries that made it difficult for it’s citizens to go to Cuba. I know that if you go from Canada as a US citizen, the US requires Canada to send them the names of those going to Cuba. I guess if you go from Cuba and have dual citizenship and enter Cuba with a non-US passport you would have an easier time coming back into the US since when you do get back into the US you would show your US passport.

  6. Having two passports makes things much easier. I traveled to Cuba in June using my European Union passport. I entered Mexico from Peru with the US passport, then used the EU one to enter/exit Cuba and enter Mexico again, and then used the US passport to enter the US. Much easier, much peasier. But I agree, US travelers should have no problems for precisely the reasons you list. The worst I heard was people saying to the US immigration officer they went to Cuba only to be told not to do it again. I believe the fines are reserved for obvious repeat offenders. US immigration has bigger problems to deal with.

    In my experience, you don’t pay the airport tax upon entry but upon departure.

    It can’t be reiterated enough that Americans are not prohibited from traveling to Cuba. The US government cannot legally limit its citizens’ freedom of movement. An extension of the economic embargo, the ban is on spending money in Cuba. It would technically be possible to not spend a dime of your own money in Cuba, for example if you had a friend there paying for everything, including the airport tax, which is paid before you go through the exit passport check. I agree on not buying identifiable souvenirs, but then, there’s little to buy in Cuba in the first place.

    And Cubana is the cheapest option, but probably the worst. My flight from Mexico City to Havana was 13 hours (yes, that’s thirteen) delayed. I lost one Cuba day on that one. Returning it was on time.

  7. Thank you for the information. I have thought about travelling to Cuba for a few years and next year is it, I am going, finally! Thanks for the tips. I cannot wait to explore Cuba!

  8. Traveled to Cuba five times and just got back and now in Canada. Cuba is a wonderful place and though the politics surrounding Cuba is complicated, that shouldn’t stop you. Let’s face it, other countries have reputations worst than Cuba’s.

  9. Thank you for the article. I have a friend who would pay for everything once in cuba but I am terrified of getting my passport stamped. My friend said cuba would stamp it. He is from there and seems to know what will happen. I will traveling alone and have this awful fear. Everything I read says it is illegal for us citizens to travel to cuba. At this rate I may never be able to go.

  10. Hi there,
    Loved your article, going Cuba for two weeks on Dec 27, I am wondering how much cash I should take, I plan to go backpacker style and stay in casa particulares and such. Thank you .

  11. I just booked online thru Cubana. Going in January via Cancun. Can’t wait! Found La Casa de Ana which looks like a perfect place to start my own “cultural tour” minus the $4,000 they charge you to go “legally”.

  12. This article was so helpful. I want to travel to Cuba in January 2015 with my husband. I wanted to know how you found the casa particulares and also if you can stay at resorts as well? Also were you able to go to different cities and areas or were there any restrictions? I am a us citizen so would be flying to cancun first.

  13. Incredibly helpful piece, thank you so much. My brother and I are trying to plan a two week trip this February and I am getting super excited. I am still confused about one aspect, the booking/buying of the flight from cancun to cuba. I read the earlier comments where you mentioned that you bought your cubana flights in cash as the Cancun airport. So did you just arrive in cancun and seek out the cubana airline office? Were you not afraid that the flight you were trying to get on would be sold out? I’ve heard that if you spend more than 24 hours in mexico, even in the airport, you have to purchase a tourist visa. Im just afraid of getting to cancun and having the flights to havana be all booked up. Is there anyway to purchase them before hand without a non-us credit card? Please let me know your insights on this matter.

    Thanks a ton!!

  14. I guess my situation is different but I can’t really find the answer anywhere online. I’m a foreign passport holder living in the US under the non-immigrant visa (hence I’m not a permanent resident of the US). I really want to go to Cuba, maybe this christmas in 2015, but the phrase “all persons in the United States, and all branches and subsidiaries of U.S.
    organizations throughout the world – as well as all persons engaging in
    transactions that involve property in or otherwise subject to the jurisdiction
    of the United States” from the sanction overview always put me off despite I’m not an American citizen (though I’m studying in a state university in America).

    Just recently I have been reading so many blogs and I feel more confident that I could try to go “illegally” by myself and just don’t say “Cuba” upon my reentry to the US and don’t buy any souvenirs. That shouldn’t be a problem. However, the biggest concern is about sharing photos. I’ll be traveling with my big camera and love to share my photos on facebook with friends and people. Do you think it is a problem posting photos from Cuba on the US soil despite not declaring Cuba upon US entry? Do you think this will have any affect on me as per breaking the embargo law? So far this is my biggest concern, because sharing photos is part of the travel experience that I would like to let the World know the beauty of all the places. If I travel and can’t share my photos, then my trip is nothing and I’d rather not go.

    Thanks for a great blog!

  15. I’m traveling to Cuba in a month. I booked my flight Canada-Cuba before Obama’s announcement. I was told that don’t stamp passports, but as I’m reading blogs I reading that beginning in April of last year they began to stamp US passports. Anyone know the most recent status on this? Any suggestions in driving to Canada and flying to Cuba? Thanks for your help!

  16. Want to travel to Cuba from Cancun in February. Since Obama has eased restrictions, I have heard that Cuba is now stamping all passports, thanks Obama!!! Does anyone have recent experience? Thanks for sharing.

  17. I travelled to Cuba four years ago out of Cancun. I had reserved my Cubana flight online. Flying in the Soviet era jet was an adventurous start. I went with the Australian, Cuban Adventure Tours and they were great. The guides were 30something English speaking Cubans. Fantastic and not super expensive like the American ‘educational’ tours you can take now. We had no problems with customs. When we came back to Mexico I asked the custom agent not to stamp my passport using the phrase mentioned above. She said that wasn’t possible but we noticed she stamped it lightly. No bribe involved. Not a good idea. I can’t wait to go back. Love the people, the music, everything.

  18. One more question, the immigration officer looks at the two entry stamps on your passport and sais “what’s this?” You say what??

  19. This is some very helpful information you’ve provided however, I just might be reading / interpreting this wrong, I will be traveling from Madrid to Cuba then departing from Cuba to Mexico and walking across the border. I am a US citizen but won’t be participating in any of the pricey “visas” the US offers; do I still need to purchase a visa? Can I do this at the airport in Cuba? Is it even necessary? Hope to hear from you soon 🙂

    Thanks in advance for your time.

  20. Thank you for writing this article. I’m planning a trip to Cuba in September but my stomach is in knots thinking about what would happen if a USA immigration officer looks at the two entry stamps on my passport into Canada or Mexico and asks where I was in between that time. I would DIE. Once I get past that fear I think I’ll be all set.

    Anyhow – do you know which Canada airport I can fly out to Cuba from? Will I be able to purchase the visa/ tourist card there as well or is it just possible to do this in Mexico. I live in NY and I’m thinking a drive or flight to Canada would be wayyyyy more affordable than traveling down to MX. Also – would you mind sharing how I can reserve hotels down in Cuba? Is it Ok to book online from USA? Look forward to your response. Cheers!


  21. Hello! I’ve read your article coincidentally! It’s very interesting and thought It could be very nice if you allow me to translate this article from English to Japanese and post it in my blog site. I’m also into Cuban culture and spent time there studying in Havana University for 2 months. I’ll wait for your answer, thanks!

  22. Do you know anything about how the changes to US-Cuban diplomacy will affect travel to Cuba. I mean, is it worth waiting? Are they already looking the other way? or, just go ahead with your plans?

    Thanks for a great well written information site!


  23. This is the most helpful post I’ve read in all of my research to Cuba. I heard about needing to purchase a tourist card/visa from the departing country before entering Cuba. Departing from the U.S. it’s around $20. Is this tourist card/visa only if you are entering legally from the U.S.? Or does this also apply if we enter Cuba from Mexico as a gateway as well?

  24. Hi! What a great post, very informative. I am traveling to Cuba in August, but we booked our hotel online so we do have some sort of a paper trail. We also booked the flight online. Anything else you would suggest? We were planning on going to Varadero for three days, and Havana for three days. We are flying thru Mexico City so if we can somehow get Cuban customs to not stamp our passports, we should just lie to the immigration officers when they ask where we stayed and what we did? We are a little nervous about this. I have global entry as well, not sure if that makes a difference.

  25. Hello Jules & Christine,

    Thanks for writing this intriguing article.
    My fiance and I are going to Cancun for our honeymoon. We have the opportunity to arrive 5 days before our week in playa del carmen.

    I immediately began to ponder the idea of visiting Havana. Do you think 4 days is enough?

    Also, because we are both getting brand new passports, what do you advise to not get a stamp in our empty book. I was thinking applying a thin layer of scotch guard or even wax.

    Thanks again!

  26. Hi Jules and Christine!

    Awesome article. I’ve heard that you need proof of at least a 3 night stay at a hotel in Cuba before they let you in. Is this true? I would much prefer to get there and explore / figure it out on the fly as I’m going to be traveling there alone, next week.

    I’m flying through Cancun from Chicago – were you questioned prior to boarding the flight to Mexico where your final destination was / if you had a visa? Considering my flight back to the states from Cancun is 8 days later and have no other international flights booked other than Cancun to Havana round trip, what should be said to those asking where the final destination is?

  27. Hi there! Thank you for the informative post. My girlfriend and I are planning on travelling to Cuba this February. She is French, so it is no problem for her, but I am American and am feeling a bit nervous about it. We plan to fly out of Montreal in Canada. From what I understand, I need to buy a Cuban tourist visa card, or some people have said they give one out on the plane. Are you aware of which is true? Also, is this the document that I want to ask the Cuban customs to stamp rather than the passport? I also heard somewhere online, that Canadian officials inform the US of Americans travelling to Cuba? Yikes. I really want to do this, but I’m nervous. Thanks for any information you can provide. If we go through with this I’d love to leave an update for everyone on how it went. (Small note; I think the Cuban word for stamp is “cuño” rather than “cuno”).

  28. Hi there!

    Thank you so much for this article. It’s been so informative!

    You mentioned that you don’t need a license to travel to Cuba. Did you need to have a valid visitor’s visa? The Havana Embassy website says that all travelers need visitor’s visas… was this your experience? Or was just your passport enough?

  29. Hi.
    I know the laws have changed since you have went to Cuba. My boyfriend and I are planning a trip to Cuba and all my research every one says fly out of cancun…but I live in San Diego and the TJ airport is right there. Does using that typical airport throw up any red flags?

  30. Loved the article! We are going to Cuba for 5 nights next week from Toronto (we live just across the US border). We don’t have an expensive people to people tour or one of the 12 reasons. Being a travel agent, we will do at least 1, maybe 2 education day tours. We have new passports and I’m assuming they have a chip in them (not sure if that means much). One year later than your article – I’m curious what your opinion is now? Do you think I can just tell them the truth going into Canada & out or would it make things much easier if we say we are going somewhere else.

  31. Hello.

    So I recently purchased my ticket to Cuba through COPA airlines. I’m a special case I guess. I live/work in Honduras and will be visiting Cuba for Semana Santa. Once I finished my purchase the fine print said I needed a Tourist Visa card. Different blogs say you can purchase one at the airport in Honduras…is that true or common? Also wanted to know do I have to carry my insurance card or paper before they let me into cuba?

  32. Thank you so much for providing the most helpful travel info for Americans wanting to travel to Cuba! I am planning on traveling to Cuba from Manila, Philippines with my boyfriends family (they are Spanish-Filipino passport holders), by way of Madrid and from Cuba to Colombia before back to SFO. I am wondering if there is any chance it may signal any red flags to US Customs if there is the travel gap from Cuba, or if the paper-stamp is implemented, they will just see I have entered Colombia and left. Would they search through to see when I had left the Philippines? Or where that time in between had gone? My boyfriends family are getting their visas in advance as well as proof of health insurance coverage in Cuba. I am trying to avoid having to fly to Mexico just so I can get to Cuba! I saw that someone above had a similar issue and that you thought the visa would be issued in Madrid or on arrival in Havana, and I commend you for answering all our individual cases. Thank you so much and hoping I can make the trip happen!

  33. Hi. Thank you for your great artical. Me and my husband are planning to go to Cuba in April. My husband is an us citizen but also has the eu passport and I am an European with a greencard living in the us. Do you have any updates for us? Since I have to show my passport with my greencard when entering Usa I am afraid they will see it in my passport. I know this question was asked many times but do you have any new updates on the stamp in the passport? Second question: Is there a big difference if we go from Canada or cancun? 3: Since you are planning to go by end of March too, do you know how much your ticket will cost you purchasing cash from cancun? Thank you

  34. Hello! Thank you so much for writing this. I’m not sure if anything changed since this post seemed to be written a few years ago. But I wanted to fly into Grand Cayman Islands and then fly to Havana from there. Do you know anything about people who fly from GCM to HAV?

    Anything helps =) Thank you!

  35. Hi there! Have just read through all these comments and was wondering if you are back from your March/April trip yet and if you have any updates to add regarding traveling as an American in Cuba?

  36. This blog post is the reason I’ve decided to visit Cuba. I’m going to visit the country within the next two weeks. How was your most recent March/Early April trip? Did you have any issues at Cuban customs ? I’m going to kindly ask them to not stamp my passport. Also, do you think posting on social media while traveling if I have wifi can get me in any sort of trouble with the US before I return back? I will be entering the country from Cancun as you did back in 2013 and returning to Cancun before coming into the US. Any advice would be very much appreciated ! Thank you so much !

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