Almost Fearless

How to Travel to Cuba Illegally for Americans

After posting pictures the other day, I had a lot of people contact me privately asking the same thing: “Isn’t it illegal to go to Cuba? And if so, how did you get there?”



First of all, it’s only a question for Americans. Virtually everyone else can travel to Cuba, spend money there and even bring home Cuban goods without repercussions.

For Americans it’s a different story. Because of the trade embargo, it’s technically legal to travel there, but illegal to spend money. (A nice catch-22.) But here is where it gets murky… the state department says that if you want to go, you need a special permit that they will issue for exceptions. For example, if you are a journalist or for educational purposes. But you don’t need to apply for the permit, you just need to qualify for one. (Others say you do need to apply). It’s a big mess. If you look at 20 different sites, there will be 20 different explanations of the laws. If you ask the State Department, they will say, “Don’t go.”

One thing to understand, is that this is only on the American side. The Cuban government has no restrictions on Americans traveling in Cuba and don’t check to see if you have some American issued “permit”.

So is it illegal for me to be in Cuba? I have no idea. Perhaps, because I’m writing this blog, I qualify as a journalist. This is also the intent of my trip, so it falls within the guidelines. But I traveled the same way that thousands of other Americans travel to Cuba every year– under the radar.

Here’s how you do it:

1. Fly to a third country. I like Mexico because flights are cheap. But you can fly into Cuba from all over Central America and the Caribbean. (Also Canada, but I’m not sure how that works).

2. Purchase a flight to Havana through a local travel agent using cash (no paper trail). I used Cubano Air, because I heard rumors that some airlines turn over their flight registry to US officials. From Cancun, my flight was $277 round trip.

3. Arrange with your travel agent to secure a Cuban visa. These are $18 and allow you entry into the country. It took my agent 1 business day to get mine.

4. If you’re not sure where to stay, you can book a package deal with your agent that includes housing. I didn’t go this route. Instead I booked a Casa Particular, a room in a private house that is much cheaper than a hotel. Mine has a double bed, private bath and cost $30 a night. Most run from $25 – $50 with hotels being more expensive.

5. You’ve got your flight, your visa, and your American passport. Make sure you have lots of cash on hand (American dollars or Mexican Pesos or whatever, you can change it to Convertible Pesos (CUC) when you arrive). You won’t be able to use your credit card or ATM card, so take a bit extra. Turn off your cell phone. It probably won’t work, but no need to leave proof of where you were.

6. Ok fly to Cuba. If you’re taking Cubano, you’ll love the Russian aircraft with it’s noisy engines and strange seats that fold all the way forward. From Cancun it was about a two hour flight.

re7. At the immigration desk in Cuba, they will take your visa and passport. The visa tears into two parts, one page that they keep and the other that they stamp and put into your passport. They don’t stamp your passport for obvious reasons.

8. You can change your money in the airport, but your taxi driver will probably take American dollars if needed. (Mine couldn’t break the $40 I gave for the fare so I paid $5 of it with dollars).

9. There will be a queue of taxis waiting for you and a ride from the airport to Downtown Havana or Vedado should be about 20-25 CUC.

10. When you check into your hotel, they will likely ask to see your visa, so they can fill out their paper work. Make sure you get it back.

11. When you leave, the immigration desk will take the other half of the visa. Again, no passport stamping will happen.

12. Eventually when you go back into the States, you will need to list the places you had traveled to. Don’t list Cuba. How will they know you went? The answer, they won’t. Besides, you totally forgot about Cuba. Cuba? Huh? Oh right, I forgot. (I did read one report where the person listed Cuba, but didn’t get fined, just hassled.)

Ok all the obvious caveats. This is informational only, and I’m not suggesting that anyone do anything illegal, I’m just describing how it could and is done by some travelers.

What happens if I get caught?

I’ve heard that the fine can be up to $10,000, but more likely $2500. I’ve heard that no American has been fined for merely traveling to Cuba. The people getting fine are doing things way outside the scope of spending a week on a beach and drinking mojitos. I’ve also heard that people don’t get fined, they get “Letters of Intent to Fine” which is basically like a big warning. And I’ve heard that this hasn’t been tested in court, seeing as Americans we have a right to travel where ever we want, and I’m sure the ACLU would have a field day if they actually got serious about fining people. For now the threat of action has been enough to keep most Americans away from Cuba, which was the desired result.

The bottom line: I couldn’t find a single confirmed story of someone getting caught, it’s all rumor and intrigue. I’m sure there are exceptions, but really the only person that knows for sure you traveled there is the airline and Cuba.

Medical and Other Emergencies

Your US health insurance won’t be accepted, but you can pay for treatment with cash.  There isn’t a US Embassy but there is a US office supported by the Switzerland Embassy, if you really needed it.

Why should you go?

Go for the culture, the beach, the rum, the dancing, the art, the people. Go because you think it’s ridiculous that the US Embargo has lasted this long, and anything that can be given for a reason can be said about China times a thousand. Go because as an American you think you should have the right to travel anywhere where they will have you. Go because you want to see Cuba for yourself. Go because you can.


There isn’t a ton, but if you have any outside of this list, please post in the comments.

Illegal Travel to Cuba from Bootsnall

National Geographic Cuba Guide

CNN’s report on Travel to Cuba

Yahoo! Answers: Is traveling to Cuba Legal?

Business Week: Traveling to Cuba

Why Obama Should Lift the Travel Restriction and Embargo (VERY GOOD)

Christine Gilbert

I’ve been dragging my husband around the world since 2008 always with the promise that, “Yes, Drew there will definitely be hammocks there.”




    Normally, I never moderate comments. You can say whatever you want here, and I’ll let it stand. On this post I’m making an exception, because it’s too easy for a few people to ruin an honest conversation. So while I’m traveling, I’m putting my husband, Drew in charge of moderating comments here. That means he can delete or modify anything he doesn’t like without warning or explanation. (Have fun, honey!)



    • Do NOT lie about going to Cuba. When you get back and fill out your questions, where were you.. do say Cuba. When they ask you to answer more questions (additional questions just about Cuba) , reply that “under the advice of my attorney I refuse to answer these questions”. They cannot force you to answer, this is your right. KNOW YOUR RIGHTS.
      The letters of fines that only few have received are all a bluff. I believe there isn’t even a court to process any fines for traveling to Cuba, because it is NOT illegal to travel there!

  • Poor Americans! I’m certainly glad Canadians can travel in and out of Cuba without any issues. I wish I could tell you how Americans go to Cuba through Canada, but I don’t rightly know. All I know is that it does happen–quite a bit!

  • Also– just wanted to mention that it’s pretty unusual to have to wait for a day for the tourist visa. I’ve always been able to walk into the airport (whether in Mexico or the Bahamas) and buy it right along with the ticket at the same time (and have generally done so with a three hour or so window before the flight).

    Julie´s last blog post..New York Times Travel Show

  • I love the covert operations Christine. Whilst this doesn’t effect me as a UK citizen, I did hear that you could have problems getting in to the US if you had visited Cuba. I’ll have to look in to this, but Cuba is high on my list so will be interesting to know.

    Sounds like a great place!

    chris´s last blog post..Where I’ve Been

  • Great post, Christine! Fight the power!

    I hope the new president quashes this uber-silly trade embargo, if only for the cigars.

    Stevo | China Travel´s last blog post..Chiang Mai Shoulder Power

  • Hey Mark, I’m sure I speak for Christine (as well as myself) when I say that I don’t think we are in disagreement with the notion that this whole ban is an outdated notion that needs to go away. Hell, in 2004 the republican led govt nearly repealed the ban, so there’s definitely a growing notion that the ban will end soon. Personally, I wouldn’t necessarily agree that the ban makes it a more appealing trip for most people. If we assume that the number of Americans who make travel a priority and get out into the world is fairly small in proportion to the number of people here, then you take that amount and could probably cut that to 10-20% (based on some super scientific number crunching I just made up for this response) of those travelers are that truly emboldened at the challenge of making the trip to Cuba and don’t view it as just one more headache when all they want to do is lay on a beach. Yes, for that small subset there is the allure of challenging the system, but I would definitely consider it to not be an overall motivator to Joe Vacationer.

    Not sure if my point was made somewhere in there. I am not known for being very succinct 🙂

  • Getting to Cuba from Canada is easy – Cuba is a favoured Canadian destination so there are direct flights not only to Havana but to a number of other Cuban cities from several Canadian cities. Most common departure points are Montreal and Toronto, with plenty of flights, including Air Canada, Cubana, and a number of charters that ferry holiday-makers back and forth for cheap. So… all you have to do is buy your tickets online to Montreal, Toronto or another destination – and then buy a SEPARATE ticket to Cuba (you don’t want to hand your digression to US authorities on a platter, do you?)

    The embargo is indeed overdone and various people at various times have tried desperately to lift it. Unfortunately, there is a very strong anti-Cuba lobby in Florida, made up of Cuban exiles who want to make sure every vestige of Castro’s Cuba is erased before travel resumes.

    Scribetrotter´s last blog post..Solo Travel for Women

  • As far as I know, tip # 5 applies to everyone – bring cash. Foreign ATM cards and Visa cards rarely work in Cuba.

    Chris – no need to worry about being disallowed into the USA if you have previously travelled to Cuba. They probably won’t know, and if they do they probably won’t care. Millions of Canadians (including myself) have done it in the past.

    Greg Wesson´s last blog post..Ecuadorian birds and The Ten Pound Note

  • I’ve also heard that people don’t get fined, they get “Letters of Intent to Fine” which is basically like a big warning. And I’ve heard that this hasn’t been tested in court, seeing as Americans we have a right to travel where ever we want, and I’m sure the ACLU would have a field day if they actually got serious about fining people. For now the threat of action has been enough to keep most American’s away from Cuba, which was the desired result.

    This surprises me. I worked for a Canadian hydrogeologist who was told either stop working on humanitarian projects in Cuba or face massive fines and lose all contracts in the US. These were private and State contracts, mind, not Federal gov’t. The contracts got pulled and given to Americans anyway, so it may just have been a tactic. Still, I didn’t think very highly of a government that would block humanitarian aid.

  • Remember the fight club rule- you do not talk about fight club. It’s sort of like cuba. you don’t talk about going to cuba 🙂

    That said- I am insanely jealous and wish I was there. I agree with steve, i hope obama kills this embargo

    Nomadic Matt´s last blog post..The Weekly Photo: Seville

  • I have been thinking about going to Cuba for year, the minute I mention it all the lurkers and trolls on my Travel Blog say they are calling the USA government. I heard an interesting reason why the ban has not been dropped. Castro took a lot of money and land from the Mafia, as long as he is alive it will look bad if we reestablish relationship with Cuba. Technically there is a need to make good to teh Mafia, and this is the dirty laundry situation. I do not think Obama will change anything, this is just naive understanding of how the USA government works.

    Truly going to Cuba for a normal tourist is easy, it the press that has the problem, being my Blog is huge, I may have a problem.

    Andy Graham of´s last blog post..What Goes Around Comes Around

  • >> I did hear that you could have problems getting in to the US if you had visited Cuba.<<

    Could it be they do the same as the Israelis did back in the 60s/70s? A lot of Arab states wouldn’t let you in if you had Israeli entry/exit stamps in your passport. So, if you asked, the Israelis would put your stamps on a separate piece of paper, which you could discard as soon as you’d left Israel.

    Keith´s last blog post..Snow Slide Show

  • does mexico tamp your passport when you leave to go to cuba? if they do, won’t customs be like “were were you in the 10 days from when you exited mexico until you came back?”

  • Shan- They don’t. You leave mexico, cuba stamps your visa (not the passport) and when you leave they take the visa and there is only your mexican entry stamp.

    Also I’ve already traveled back into the US after traveling to Cuba with no problems.

    There is literally no proof I went on my passport.

  • Christine – I’m not sure if there is other posts I’m not seeing, but my friend and I want to head to Cuba. Can you give me specifics on how you and your husband did so? Please no sarcasitic comments from others – we are looking for real advise. We are thinking of going from California to Cancun then to Havana, that’s what seems to be the most common or least expensive. Did you convert US to Pesos to CUCs? Did you have to pay the Mexican border patrol to not stamp you back into Mex after visiting Cuba? Did you use a Mexican travel agent once you got there or just to it once you got to the airport? Did you stay a night before heading to Cuba? Thanks

  • So sorry just found the how to list awesome ignore my other post asking you questions that you outlined…thank you!!! Anyone else have any helpful tidbits I’d love to hear them – tried to ask on another site and got a lot of rude sarcastic responses. We are really just looking to get some helpful info for first time visitors to Cuba, well traveled, but want the what to do and not to dos from people who have gone.

  • Hi Shane-

    I had to look at my passport, because I couldn’t remember (it’s been eight months) but they didn’t stamp my passport again when I returned into Mexico. That being said, I only traveled to Cuba once, so I can’t speak to everyone’s experience.

    The bottom line though is that US customs is not going to notice. I have traveled to 16 countries in the past year and no immigration officer or customs officer has EVER checked my stamps. Regardless, even if some did, I have never heard of anyone actually getting busted for going to Cuba (unless they were smuggling goods or something). As I mentioned in the post, there was even a story someone wrote about how they declared their trip to customs. And they didn’t get into trouble, just questioned and released.

    So follow the steps I put here and you’ll be fine. Or if you’re too nervous just wait a bit, they’ll probably relax the rules in the next few years anyway.

  • can you email some of the travel agents you used to get you to cuba? I have a very fixed time I have free to go so I can’t wing it or take chances of showing up at an agency in mexico or bahamas.

    Greatly appreciated

  • Vida,

    You still have to buy the ticket in Mexico in cash, so you’ll still need to do that there. I’d use google and search around. It’s available with tons of agents.

    Good luck,


  • Hey Christine – quick question – did you use a US travel agent or one in Cancun? I’m meeting a friend in Cuba at the end of Feb – she’s from the UK and wants to buy her ticket now and I’m not going to be in Mexico until early Feb. Do you think I will be able to find and buy a flight in Mexico City within a week or so of wanting to fly?

    Would love your thoughts!!
    .-= Shannon OD´s last blog ..A Little Tradition…A Unique Christmas in Australia =-.

  • Hey, i have a question, i was in Cuba once and while there i thought i lost my passport, in the end i found it, but i was thinking about it… let’s say you lose your passport in Cuba what happens?

  • My uncle tried to travel to Cuba from Mexico. He was stopped and sent back before he could leave the airport. It was a hassle for him and kind of a bummer, but nothing bad happened like a fine or jail or anything like that.

  • My uncle tried to travel to Cuba from Mexico. He was stopped and sent back before he could leave the airport. It was a hassle for him and kind of a bummer, but nothing bad happened like a fine or jail or anything like that.

    Also, to Joe about the passport question. Some friends of mine went to Cuba (with visas, authorized by the U.S. government under one of the exceptions). A member of their group lost her passport, and it was replaced by an unofficial embassy-ish kiosk the U.S. government apparently maintains there. Mind you, she was there with the U.S.’s blessing, so that probably helped.

  • I hope they never lift the American travel restrictions on Cuba. As a well-traveled American (18 countries) I’ve seen first-hand how my fellow Americans can ruin the experience

  • Rachel,

    When I went, I didn’t have a reservation…

    However, it’s not illegal for Canadians or British citizens to stay in Cuba, so there are plenty of websites that have listings and allow registration.

  • Just got back from Cuba and yes the cuban gov doesent stamp but the Mexican gov does so I had 2 entry stamps and yes our customs does notice and if you falsify you entry form, you have made a bigger violation than by simply going to cuba. With this declaration we were wisked into the back room ask to fill out a form and they searched our baggage. They then indiacted that we may be contacted by the stated department within 20 days. If we are not that is it.

    With all said the trip was one of a lifetime as the culture, people and music were beyond reproach.

  • Question is this is still an active post: does mexico stamp you on exit and re-entry? Do I need to be prepared for that when exiting Mexico for Cuba and when returning through Mexico?

  • If possible i would go through canada as they are cool about not stamping your passport upon re entry into their country….canadians are the best :)))

  • Thank you for the great advice. I could not agree with you more. Americans that enjoy freedom, but allow these pointless travel restrictions to exist are a bad paradox.
    With that said, I want to mix it up a bit. I plan on traveling to the Dominican Republic. What is the best way to travel to Cuba from Santiago? How much is airfare to and from roughly? Should I book this flight now or wait until I my first day in the Dominican Republic? Is there a better airline to take? What about a boat? Also, what about a plane to Jamaica and then a boat to Cuba? So I would fly into the Dominican Republic, spend a few days there, maybe cross the border in Haiti for a day or two, then go to Kingston, boat to Havana (or fly), then fly out of Kingston back to the US. Perhaps the Jamaica twist might be too much for this trip. However, I will definitely be flying to the Dominican Republic first, going to Cuba, then back to the Dominican Republic before returning back the US.
    I have read that foreigners are required to have at least three days of living accommodations paid for before entering Cuba, is this true? What is a good resource for picking housing? I always enjoy staying with local people, but I would also like to check out a couple of more swanky beach hotels on my vacation. I imagine importing Cuba cigars is a really bad idea, other than some small “Dominican” items that might find there way in my carry on, what else is a really bad idea to buy? Finally, I like to take a ton of photos and maybe even some video. Should I mail this images home from Dominican Republic on DVD or flash drives, upload it into cyberspace first, and erase my SD and memory cards or is that too paranoid. I do not want to give the KGB, I mean the State Department any reason to confiscate my cameras and personal items.
    Thanks again, this is really a very good resource for people who enjoy travel and demand freedom. You think they would allow this embargo to dissolve out of embarrassment. A water slide on the moon would make more sense and be more effective than this ridiculous foreign policy blunder.

  • im afraid of the new microchip they had installed in the new passport. satellite.
    anyone knows?

  • Christine –
    Has much changed with your procedures to get to Cuba since 2009. It is now 9/2012 and I am thinking about a trip to Cuba. Anything new? Please reply privately if necessary.
    Many thanks! -Jim

  • Hey Christine,
    Along with Jim I’m also wondering if you know how things have changed since 2009. You mentioned booking casas particulares. Did you book from the US? Through an agency? We’re hoping to avoid agencies, or book with a good Cuban one, but unsure of how to proceed…

    • I haven’t been back since 2009, so I can’t offer first hand experience but I haven’t heard of any changes. You can ask around on the Lonely Planet forums for a more recent experience

      For booking hotels, if you’re American, you can’t use your credit card for anything Cuba related — even if it goes through, because it’s with a third party (like an agent) I would be really hesitant to put myself on the record as having purchased hotel/airfare for Cuba. If you’re not American, you can do whatever you want! lets you book some casa particulares, but when I went in 2009, I just booked when I got there, walked around and looked at different ones and then paid in cash.

      • what about the entry stamp in Mexico (or Canada) don’t they see you entered Mexico and then re-entered Mexico? What if they ask you “where did you go”??

  • Lots of great advice here. Thanks for sharing the article.

    Based on my research, It is possible to get there from Mexico, but you do risk Mexico stamping your passport upon re-entry. For me that re-entry stamp would make me paranoid. I can lie my way out of something, but when you have the proof in front of you, then what? Jose Baez? Don’t know if I’ve ever noticed a customs agent looking that closely at my passport, then again I never had reason to pay attention.

    If by chance you DO get caught, below is a quote from Wikipedia:

    …”Making false statements to USCIS agents can be added to the charges if you falsely report your travels (e.g. omitting Cuba) at the POE (port of entry). This problem leads some travelers to give an honest declaration along with an attempt to justify their visit under the general license if they come under scrutiny. Others simply omit Cuba and take their chances. Invoking your Fifth-Amendment right to remain silent may also come in handy when filling out forms or answering more questions whose answers might incriminate you. Simple advice is to smile, then decline to chat because all this traveling has made you tired.”…

    According to most resources, the only way to make things “messy” so to speak is to bring articles back with you that actually incriminate you -clear your luggage of all tags and anything Cuba related and you’ll be fine, even if they do find out.

    Echoing what Christine said, I’m hearing over and over that nobody gets prosecuted. You may get questioned, receive letters of warning, but you contest and they don’t pursue it.

    I don’t know. I think I’d plead the fifth.

    I’ve also read via Wikipedia that in the Bahamas, Costa Rica, and Jamaica, U.S. Customs Pre-Clearance facilities now exist at many of their airports.

    The link is here:

    The best third party alternate routes may be Barbados (?), Cayman Islands and Canada to avoid getting your passport stamped on reentry. Cayman Island tourism can tell you how to avoid passport stamp – haven’t heard firsthand how from anyone so it’s obviously hush hush and nobody’s fessing names of travel agencies, but I was told to look at the agencies that have “cuba” listed on their door.

    Nice point about the microchips in the passports – hadn’t thought about that, but then again who am I? LOL.

    Also, good point about losing passports. Something I had also wondered. Basically I’m guarding it with my life.

    Thanks again Christine for a great article.

  • I am an American citizen and I have just returned from spending 10 days in Cuba. I live in Arizona and traveled through Canada to avoid the Mexico double passport stamp issue. I was also traveling with a group of Canadians, so that route just made sense. I booked a package deal through a Canadian travel agent and they only needed my full name, date of birth, US passport number, and payment.

    On entering Canada, I stated to the border agent that I was flying to Cuba for 10 days and would return again to Canada before re-entering the US. She questioned my logic of flying from Arizona to Canada to Cuba but it was sufficient to state that I got a great deal from a Canadian travel agent, which was completely true.

    The border agent in Cuba didn’t care in the least that I was American. The only difference in treatment I received versus my Canadian friends was that I had to show proof of a traveller’s health insurance policy. I had purchased a policy before the trip and I simply presented the insurance document and was granted a visa for the standard 90 days.

    Traveling back from Cuba to Canada was completely uneventful, just be aware that everybody leaving Cuba has to pay a 25 peso exit fee in CUC currency at the airport.

    Please understand that I am not proud of the following, nor do I condone such behavior, but since I completely disagree with the Cuban embargo and find it inhumane, I lied to the US border agent. I said I was at my Canadian buddy’s wedding (true) in his home town, Nanaimo (wedding was actually in Cuba). The agent asked me if I took a ferry back to the mainland and I lied and said yes. He asked my occupation and that was it, welcome home. My baggage wasn’t searched, but I made sure beforehand that none of the items I was carrying indicated that I was in Cuba.

    I’ve been home a week and I am already making plans to return. I will consider telling the truth at the border next time. If it backfires and I am fined, I would love to be an ACLU test case that exposes the embargo as the cold-war anachronism that it is. Thanks for the info.

  • Lets say I flew to Peru for a week one way and then flew to Cuba one way for a weekend, Can I take a flight to Miami and then back home to Ohio without any hassle. One more question. Can I bring back souvineers from Cuba? Thank you all in advance.

  • Hi Christine. When you state that you purchased a flight from Cancun to Cuba did you make prior plans? Or did you find a local travel agency the minute you landed in Cancun to purchase the flight? I’m looking into traveling to Cuba later this year. Thanks!

  • You can’t go from Canada anymore. US customs had set up camp for all flyin’ flyout American citizens and they double check where you are going and have been before boarding. The only real way from Canada now is to join some kinda Cuba Tour group.

  • Interesting conundrum for Americans… I can certainly understand why many Americans decide to experience Cuba under the radar. Thanks for posting this, interesting read for us non-Americans too!

  • I beg you to change the multiple “American’s” in your article to “Americans.” You’re describing the plural form of American, not the possessive, so the apostrophe is not needed. This repeated mistake distracts from what is otherwise helpful information.

    • Thanks, good catch, fixed. What’s worse is that it’s been like that for five years, yikes.

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