Americans Traveling to Cuba Illegally: How To Do It Right

Before Jules and I bought our tickets to Cuba I’d spent hours searching the Internet for information on traveling to Cuba as an American. I knew it was technically illegal, but just how illegal was it? There were few articles of Americans traveling to Cuba who had written about their experiences.

I read a lot of conflicting information. Some bloggers encouraging me to go, others warning of the heavy fines and possible prison time for breaking the law. I was so confused I almost gave up and didn’t go. The myths of Cuba were almost enough to put me off!

Thank God Jules talked me into it because Cuba ended up being one of my all-time favorite countries. And now I love the fact that I went illegally, because seriously, the travel restriction is so antiquated and ridiculous. So here I am, proudly announcing to the world that I, Christine, have traveled to Cuba illegally. And here’s how you can too:

Isn’t it illegal?

Yes, but under the Obama administration the US government is easing up on restrictions for visiting Cuba. Certain organizations likes school groups, choirs, religious orgs, etc  may be granted special visas to visit. This is how Jay-Z and Beyonce went legally. They went with a  Museum Foundation and their trip was tailored to meet certain education requirements.

Person to person tourist groups are also being allowed access, but for the average traveler these options are pricey and often inaccessible. As far as the Cuban government is concerned, come one and come all! They welcome all American tourists and hold no grudges.

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?

Theoretically it is not illegal to go to Cuba, but it is illegal to spend money in Cuba. But since you have to pay an airport tax the minute you enter Cuba, you’re screwed from the beginning. 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. In fact, no American has been fined for traveling to Cuba in the past 10 years, and believe me there are a lot of American illegals making the trip every year.

 

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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.

buy the authentic cuba travel guide

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.

 

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How Can You Buy a Plane Ticket?

Buying flights to Cuba has never been easier now that the US is starting to reduce their restrictions for travel. But it wasn’t always this easy. Back when we first went in 2013 it was more difficult and we had divert through Mexico to buy the tickets in cash. Now it’s much more simple, but still requires some essential information. To get the full story click the graphic below.

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 I felt very welcome in Cuba. Locals were very interested to hear about life in the States and I never felt a 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.

 

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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 it was easily one of my favorite countries I’ve ever visited. The people are incredibly friendly, I felt 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.

travel insurance for cuba

87 thoughts on “Americans Traveling to Cuba Illegally: How To Do It Right”

  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)
    Thanks,
    richard

    • 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!

      • This is probably a stupid question, but when you’re in Cancun, do you just buy roundtrip tickets? What’s the process getting back into the states?

        • Hey Nancy, not a stupid question! We did buy roundtrip tickets when we were in Cancun. Then getting back to the states we flew from Cancun to SFO. As long as you don’t tell them you went to Cuba (ie. don’t put it on your immigration form, you’ll be golden. Have fun!

  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.

    • We only ever stayed at casa particulares, which are ran by local Cuban families. The whole time in Cuba we only ever used cash to pay for things, it worked out a lot easier. Are you thinking of going?

  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.

    • Yea, I think its just US citizens that have a hard time getting into Cuba. Lucky us! But going through Mexico was seriously no problems. The Cuban govt doesn’t stamp anyones passports so as long as you don’t have any souvenirs (unless you hide them well) then the US immigration will have no idea you’ve been there!

  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.

    • Thanks for your input Peter! Yes, I think there is a lot of fear instilled in Americans about traveling to Cuba and the country in general. I was pretty nervous about going but once you arrive in Havana you realize that Cubans are so welcoming to Americans! That’s so nice that you have two passports! I’m jealous! I would absolutely love an EU passport! I’d probably never leave Europe! Haha.

      Sorry to hear about your delayed Cubana flight! I guess we got lucky. It definitely wasn’t the best airline but we are usually looking for the most budget friendly. Glad you had a good time in Cuba!

  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.

    • Hmm, when we went they just stamped a piece of paper stapled into your passport which they remove when you leave. They did this for all the nationalities, not just Americans. I would be very surprised if they stamped your passport. They want Americans to visit and if they did that, Americans would get in trouble and stop going. I wouldn’t be too worried if I were you. We didn’t have any problems!

  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 .

    • It really depends on your style of travel and budget! We spent about $100/per week but we did it pretty bare bones. If you are on a two week holiday, you probably want to splash out a bit more. I’d say $200/week is a conservative estimate but you could do it cheaper or more expensive depending on food, drinks, tours, etc. Have fun!

  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”.

    • Not if you’re only going for a holiday. Are you from the States (just going off your verizon email address), because if so you definitely won’t be able to get one. Just show up at the Cancun airport and they process it automatically.

  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.

    • Hey Jessica thanks for stopping by. So happy to hear you’re off to Cuba, it’s such an amazing place! Definitely get to Cuba this Jan, it’s a great time. We found the casas through a pretty specific network, from a woman we stayed with when we first arrived in Havana. We wrote an article about it as well. There are plenty of resorts to stay at, look around Varadero for some of the popular ones, or perhaps Playa Ancon. No restrictions as far we saw. Hit us up if you have anymore questions. And please email us once you’ve returned and tell us how it was 🙂

  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!!

    • Hey Corby! So glad we were able to help you plan your trip! We were in Mexico already so we had passed the 24 hour limit and had to buy a visa. As far as flights, we had been checking in with the Cubana office online and on the phone in Cancun to see if they were close to selling out any of the days we were planning. I would recommend giving them a call and see if there’s anything you can do to reserve a ticket without paying, ask their opinion on what days might sell out, and then try to give yourselves a couple of days to be flexible. If you have more questions about it, shoot as an email at [email protected] Good luck!

  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!

    • Hey Ken thanks for sharing. I’m no immigration expert, but i would be very very surprised if any of the US laws affected you, seen as you’re not a US citizen. Plus they are super lax anyway, and you don’t need to worry about it. We went to Cuba illegally, and have been posting about it all year and haven’t heard anything about it, so you should be fine. Enjoy your trip and get some awesome snaps, but remember it’s not always just about the photos and sharing them. Try to immerse yourself within the Cuban culture away from the lens, that’s when you’ll find your best photo opportunities pop up.

  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!

    • Hey Will, we’ve also heard from a few sources that they may be stamping passports, but that you can still get them to stamp a piece of paper. We’ll look into it with our connections and try get back to you.

    • Nah it’s totally do able and not scary at all. You’ll be right. Thousands of Americans visit Cuba illegally every week and there’s no dramas. Christine was pretty worried at the start as well, but it worked out fine 🙂

  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.

    • hey Valerie, we have heard a few rumors about this, but we also heard it can be avoided if you make sure to ask them beforehand. If you go please let us know how it goes so we can update the page if need be 🙂

  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.

    • Hey Kathryn, we didn’t seem to have any issues with that. They didn’t check our medical insurance at immigration, like some places say. I assume a print out of your insurance receipt/ proof of insurance would be enough. I doubt US based insurance companies cover travel to Cuba, but you shouldn’t have any problem entering the country with an American insurance. Like I said, that’s if they check at all.

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

    • I wouldn’t worry about it, actually. They didn’t ask me and I don’t think they look hard enough at the stamps in your passport. They’d have to look at each stamp and check each day and do the math in their heads to think about having two entries. I know that’s not a very comforting answer (I was worried about this too), but I honestly wouldn’t worry about it!

  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.

    • Hey Andrea thanks for the message. There is only one official visa to get into Cuba (from the Cuba side) and it costs $25USD. When we flew from Mexico we purchased it at the Cancun airport, so I’m assuming you’d do that in Madrid, or when you land in Havana. Should be pretty straight forward 🙂 Enjoy your trip!

  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!

    GG

    • Hey GG (if that is your real name haha). I understand it can be nerving, but tens of thousands of people do it and have never had any problems. As for the passport stamps, I don’t think they’re too worried about that. Unless your passport is brand new and only has two stamps on it, then not sure. You might need to do some more research on that sorry. As for the Canada airport, you’re probably best to search flights through airlines that fly between Canada and Cuba to check that. We flew from Cancun and flew with Cubana Aviacion. As for booking hotels online from USA just use incognito mode on a public computer in the library 🙂 Think you’ll be fine, but you probably shouldn’t use your US credit card to try and book anything. That’ll be a red flag for sure! Let us know if you’ve got any other questions, or come on over and visit our Cuba travel forum to see what other travels have to say 🙂

  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!

    Liana

    • Hey Liana! From what we know things are changing fast, but it might take a while before the changes are evident for the average traveler. It’s inevitable that the loosening of economic sanctions will create large investments and development from the US, this will undoubtedly create things such as McDonalds and other rubbish corporations that liter the West. Take the risk, head to Cuba before it’s too late! Be sure to let us know hwo you go once you get there, we’re thinking of going back to the South of Cuba next year 🙂

  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?

    • Thanks Hazmeena! the tourist visa card is required by Cuba, so wherever you fly from you’ll need to purchase one. We purchased it from Cancun airport flying to Havana. Just make sure you don’t pay at both airports. Enjoy your Cuba trip!

  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!
    -Jason

    • Hey Jason! Thanks for dropping by! Umm 4 days, that’s cutting it a bit short, but totally worth it if you’re not bothered by the financial cost to get out there. Havana is amazing and you would definitely get a good fix of the life. But i guarantee you’ll be back haha. As for the passport… we always get similar questions about empty passports. You won’t get a stamp from Cuba, but are you worried about double stamps from Mexico? Cheers.

  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?

    • Thanks Kyle. As far as i know nobody has been asked about their accommodation, but this could be a new development. Please do let us if this is true or not and we’ll update or info 🙂
      In terms of final destinations just say it’s Mexico. We were already in Mexico at the time so it wasn’t a problem for us. They don’t have access to flight manifestos, so just say Mexico is your last spot and nothing else. Good luck!

  27. Hello, we are trying to go to cuba. My husband his french. But my kids are francoamerican i have us pasport living in europe We are going to nyc. To visite family and after going to cuba and coming back nyc again. Before going back to europe. Do you think i should go by canada since its not far from nyc. Rather than mixico? My husband he has no problem becaus he is European but me and my kids. Anyone who has been to cuba the last 6 month please let me know. Thank you.

    • Hey Belle thanks for getting in contact with us. I would say that if you’re already in NYC then flying from Canada would make more sense. I know it’s easy to get a flight out of the east coast. But it also depends on whatever is cheapest i guess. If anyone else have updated info on transit routes please feel free to share.

  28. 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”).

    • Hey Kiah thanks for messaging us. You shouldn’t worry about the Cuban tourist visa, the airport/airline will take care of that. This is the document that you will get stamped when you arrive, and when you leave they will take it out. They’ve dealt with literally tens of thousands of Americans this way, so no need to stress. As for the Canadians telling the Us, i highly doubt that. No nerves needed, all good! But please do send us an email with your updates once you get back, we’d love to hear them 🙂

  29. 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?

    • Thanks so much Ashely 🙂 Glad it was helpful. Yes you do need a visitors visa, but you can simply obtain that the airport before or after you arrive. It’s an easy process and you don’t need to organize anything before you go 🙂

  30. 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?

    • Hey Stephanie thanks for commenting. We flew out of Cancun, as do most people, and we don’t really know about TJ. I’d assume it wouldn’t make much difference, but unfortunately we don’t know for sure. If you find out we’d love it if you could let us know. That was we can pass on the information to future travelers with similar questions. Thanks 🙂

  31. 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.

    • Thanks for commenting DD! Things have definitely gotten a lot more lax but I’m not sure it’s lax enough to admit that you’re breaking the law. The only trouble with having a new passport (don’t think the chip matters at all) is that you’ll have a gap between when you leave Canada you’ll have an exit stamp and entrance stamp when you come back in, but no stamps in between that time. The fact of the matter is that millions of Americans go to Cuba every year and have been going long before the Obama administration. As far as I know, no Americans have gotten into trouble for going to Cuba in a long, long time. I wouldn’t worry about it. Have fun!

  32. 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?

    • Hey R.Loew thanks for dropping by. For the Tourist Visa card we just received that at the Cancun airport before we boarded our flight, so i assume you’ll receive it in Honduras, but either way you’ll get a chance to buy it because they want the visa money. I wouldn’t worry about that, i dare say those other blogs are correct . As for insurance, we were never asked about whether we has insurance or not. Thankfully, because Christine actually didn’t have any at the time. So you should be fine. Do let us know about getting your visa card from Honduras though 🙂

  33. 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!

    • Hey Jessie, thanks for commenting! Glad our information has been helpful! As far as having a “gap” in your passport between Colombia and heading back to the US, I wouldn’t worry about it. I was very nervous about that exact thing the first time we went but it wasn’t a problem at all. They really don’t take the time to look at each individual date and place it together in a timeline. As far as the visa, we got ours in Cancun airport before flying to Havana so I assume whichever airport you go to will issue you the visa, but you can call them and double check. When are you heading to Cuba? We are going back late March/ early April and will be updating our info so check back!

  34. Hi.

    Im planning a trip to Cuba in June and really appreciate all the info you have posted. It’s been difficult trying to understand the laws and required documentation (travel visa). People have told us to try contacting the consulate in DC and/or to go through a tour company but the prices are ridiculous! I will be in Cancun for a few days in June before going to Cuba and just wanted to ask if you have learned of any updates that I should be mindful of. Im interested in staying at the casa’s particular’s and also wanted to ask if you had any recommendations for us. I was looking for tickets on online, but sounds like I should try once in Cancun…..

    Thanks so much.

    Thanks

    • Hi Stephanie, thanks for getting in contact with us. Glad our posts have been helpful. The laws are definitely confusing! We have not been back to Cuba since 2013 so the laws have changed quite a bit. You can go with a person-to-person tour, or you can go illegally through Cancun which is what we did. We have an American friend who went very recently in the past couple of weeks and he said he didn’t have any problem going over/ coming back. We bought our tickets through the Air Cubana office in Cancun and took out money at the ATMS there, although now Americans may be able to use their ATM cards in the country. As far as the visa, we got ours in the Cancun airport super easy.

      With the Casa Paritculares, most of them aren’t available online so its more just showing up and seeing whats around. If you want you can do what we did and start your stay in Havana at Hostel Hamel. They can sit down with you and give you a list of casas they recommend in their network. We payed around $10/ room after a bit of haggling. You can also just show up to a town and the houses that host people will have signs on their doors. It sounds confusing, but it’s actually super easy!

      We’re headed back to Cuba in late March/ early April and will be updating all our information about traveling as an American so check back in then!

  35. 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

    • Hi Sarah, we just got back from Cuba. If you go from Canada or Cancun then the immigration in Cuba will ask if you want your passport stamped. They are very sensitive to the fact that most Americans still can’t legally go to Cuba and don’t want a stamp in their passport. That being said, I wouldn’t worry about it at all. The Obama administration doesn’t care about people going illegally to Cuba. I went, had my American passport stamped and came back into America with no worries. I’m not sure if immigration saw the stamp and didn’t care, or just overlooked it, but they didn’t even ask me about it. There are 12 “legal ways” for Americans to go to Cuba, it’s completely self-licensed so I suggest you just pick one that sounds most applicable to you just in case they ask. But again, I wouldn’t worry about it. For prices, you can check airline search engines.

  36. 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!

  37. 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?

  38. 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 !

    • Hey Michelle! That’s so awesome to hear. We’re glad we’ve provided some inspiration and assistance in your up and coming trip. We had a blast after returning. You might mis our latest updates before you leave, they’re all going up in May. In very short… no issues what so ever with customs. Christine had her passport stamped and went through US customs with it. That’s how easy it is 😀
      You’re legally allowed to go now (more or less) so there are no restrictions! Post away and be sure to send us some pics 🙂 Let us know how the trip goes.

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