Yankee in a Che Shirt: How To Travel to Cuba Independently and Illegally as an American

Americans you're likely to encounter in Cuba

Si, se puede!

Three years ago, I traveled to Cuba. I didn’t get a visa, didn’t book a tour, didn’t go with a dance troupe or salsa band (though that would have been killer). I did it the way I do everything, independently.

Fear mongers, nay sayers and foreign travel agencies would lead you to believe that independent travel to Cuba is dangerous and impossible. They’re the same people that make full and complete stops at every stop sign, and are too scared to ride the subway in NYC. Or else they’re trying to sell you something—the hustling taxi driver outside of the airport. They clamor cowardly behind the embargo.

Here’s the legality deal: as an American, you’re technically not banned from traveling to Cuba; you’re prohibited from spending money there. Whatever. If you didn’t obey your parents’ curfew as a teenager, are you really gonna start heeding authority now?

The fun thing about traveling to Cuba as an American is that it requires more effort, more digging. You can’t buy your plane tickets online; most worthwhile advice won’t come from guidebooks but fellow travelers, via forums like Thorn Tree. Basically, you have to work a little harder. But the reward is getting to go to one of the most un-Americanized countries in the world—remarkably only 90 miles from Florida.

I’m pretty sure it’s technically illegal to give Cuban travel advice to Americans. But eff that too. Here’s how I did it, how it worked and the gems of wisdom I smuggled back (along with the cigars):

Before You Go: Money and Packing

Your most important pre-travel preparation as an American is money. Your ATM and credit cards won’t work in Cuba, meaning you’ve pretty much got to bring everything you plan on spending with you. Travelers checks are a pain in the ass and have a hefty commission tacked on—which means you’ll be bringing cash. Lots and lots of cash.

If you’re like me, you’re not too thrilled at the idea of walking around with $1300 on your person. But keep in mind Cuba’s remarkably low crime rate, the absence of desperate drug addicts and your own street sense—you’re gonna be fine.

Another consideration is which type of currency to bring in. The greenback gets an extra 10% penalty fee on top of the standard 8% exchange commission, so most travelers opt to bring in Canadian dollars or Euros. It pays to do the math on conversions and figure out how much you’ll be hit by commissions and fees for dual exchange (changing from dollars into Euros into CUCs).

Another pre-trip consideration is what to bring, and what not to bring. This is for everyone, not just Americans. Charitable donations like medical supplies and clothes are greatly needed and appreciated, but check out regulations on what and how much to bring. Cuban Customs has some unusual regulations regarding the import of electronics and pornography, and is super strict about narcotics. Of particular concern to Americans is the prohibition of anti-revolutionary literature—make sure you don’t have any crazy right-wing, Miami ex-pat ramblings with you. Not that you would anyway.

Getting In: Booking a Flight

The easiest, most popular and often cheapest way for an American to get into Cuba is through Mexico, namely Cancun. Of course, Cancun is the #1 most suspicious transfer point, and word around the chat rooms is that you’re singled out by US Customs most often when arriving from Cancun. But it’s also an insanely popular destination, and I think the Mexican- to Cuban-vacationer ratio still works in your favor.

American travel agencies and airlines are prohibited from booking flights or giving any kind of assistance to Cuban travelers. But foreign airlines and agencies aren’t. So instead of shelling out big bucks to some Canadian company that’ll orchestrate the whole thing (for a mere 300% mark-up), do what I did: call a foreign airline at one of their international offices. I called Mexicana in Mexico City (52 55 2881 0000), requested to speak to an agent that spoke English (not a bad idea when purchasing something as expensive as plane tickets), and bought tickets from Mexico to Havana. Not as easy as Orbitz, but pretty damn close.

The way the flight times worked out, we ended up bookending our Cuban travels with overnight stays in Mexico. I thought I’d be smart and fly through Merida, whose Sunday night dance parties sounded infinitely preferable to Cancun’s binge-drinking co-eds. Turns out that you can’t fly directly from Merida to Havana, so we had to transfer in Cancun anyway. Ah well, better than a spending a night in Cancun.

Arriving: Surviving Customs

Passing through Cuban Customs is the most intimidating border crossing I’ve ever done. But, as I reminded my then-boyfriend and travel companion, Cuba wants to let you in. They need tourists’ money. They just wanna make sure you’re not there on an anti-revolution espionage mission. Fair enough.

Expect to stand in an impossibly long line. You’ll be instructed to approach the Customs booth by yourself. They’ll scowl at you, tell you to take off your glasses and look into the camera. They’ll photograph you, record you, enter every last bit of info on your passport into their computer. They’ll then stamp your tourist card, your golden ticket. Cuba doesn’t stamp passports, but $20 purchased tourist cards. Mexicana provided mine, but it’s a good idea to check your airline or prepurchase your card at a Cuban Embassy, as getting ahold of one at the airport sucks. And hang on to that baby—losing it is an expensive, bureaucratic hassle.

Once your passport is handed back to you, you’ll get directed through the floor-to-ceiling solid door that the travelers before you disappeared behind. It may seem like you’re being funneled into an interrogation room, but most likely, you’ll be headed off for a quick frisking and x-raying of your baggage. Drug sniffing dogs will accompany female agents in ridiculously short skin-tight mini-skirts—the most amusing part of your Customs experience.

While You’re There

Really? Couldn't have left the Confederate swim trunks at home?

Once you’re in Cuba, there’s not a lot in your day-to-day travels that’ll set you apart as American. You’ll have to deal with the money issue, but the good news is that everyone will guess you’re from somewhere other than the US. It’s a nice change of pace from the Frenchman breaking into sudden English with, “And where in the States are you from?”

Getting Out: Playing Dumb and Looking Innocent

The trickiest and most anxiety-inducing part of any American’s trip to Cuba is coming home. I’ve heard of Americans getting hassled by Cuban customs agents, but it’s pretty rare. The folks you have to worry about are the good ole’ boys (and girls) back home.

But first you have to worry about a double-entry stamp back in Mexico. This means that you’ll have a stamp for arriving in Mexico, no stamps for Cuba, but then another entry stamp for your return to Mexico; there’s a void in there, signaling nefarious activity.

You can handle this one of two ways: bribing the Mexican Customs agent to not stamp your passport (trickier at Cancun, where they’re more vigilant, but still possible), or by hoping for the best with a doubly stamped passport. We opted to bribe the Mexican Customs agent. We tucked a sizable peso note into our passports and softly asked not to be stamped. The agent grunted and handed us back our passports, unstamped. If you’ve got a heavily stamped passport to begin with, it might be worth saving the money and relying on the slim odds that the US Customs agent will bother to inspect your passport closely. I’ve never had an agent more than glance at my stamps.

Aside from the extensive, albeit poorly edited, advice by eco-hippies International Bike Fund (I mean that in a good way), any American who’s ever traveled to Cuba will be eager to give you plenty of tips and first-hand accounts on how to elude US Customs—whether you want to hear it or not. So here’s my two centavos:

Revolution anniversary poster I stole and smuggled back home

Reports vary, but up to 100,000 Americans are claimed to have visited Cuba last year. Most of them breeze through US Customs without a problem. There’s nothing that should single you out as particularly suspicious. Be respectful; don’t roll up to the counter smoking a cigar and wearing a Che hat. But don’t sweat it too much. Customs agents are doing their job, and you’re doing yours. They really don’t want to write out lengthy reports anyway. I truly regarded my traveling to Cuba as not too dissimilar from jay-walking—not supposed to really do it, but no big deal. Folks’ll tell you not to bring anything incriminating and obviously Cuban back with you, but eff that—I brought cigars and stolen street posters.

We arrived at SFO disheveled and tired with a horde of sunburnt vacationers. I of course did not write on my Immigration Card that I’d traveled to Cuba, nor did I list the goods I was smuggling back (why you gonna rat yourself out?). I smiled nicely at the agent, told her yes, I’d had a great time in Mexico, picked up my bags, passed em through the x-ray machine without incident, and headed home.

But enough out of me. Any Americans out there wanna share their Cuban travel experiences?

38 Responses to “Yankee in a Che Shirt: How To Travel to Cuba Independently and Illegally as an American”

  1. 1 Jessica December 30, 2009 at 5:47 am

    You are awesome! Great post. All I can say is thank you, thank you, thank you. We really needed this info as we plan on going to Cuba early next year. All the info I found about Cuba prior to this was fear mongering crap, all about how you are going to be hassled. Stuff like-beware of the evil Cuban customs agents-they will undoubtedly stamp you passport and you will be killed when you get back to the States. A bunch of bull, so thanks for putting some truth out into the world.

    I am so excited to visit Cuba, have been dreaming about it for years. I will keep you posted on our experiences once we get to that leg of our trip.

  2. 2 T-roy December 30, 2009 at 8:08 am

    I remember the female custom agents in Havana! They were dressed like hookers with their fish stockings and short skirts… but I will say they did look good in them. But it wasn’t just goven’t employees who wore this attire but a lot of office ladies. I seen so many women all wearing the same thing and I couldn’t help but laugh every time. Cuban fashion is about as desecrate as the revolution! lol

  3. 3 T-roy December 30, 2009 at 9:28 am

    Lauren- I also made a post on http://www.gobackpacking.com about Americans going to Cuba. You can check it out here:


  4. 4 Abbie December 30, 2009 at 4:54 pm

    That’s a great guide, I never considered the double stamp in Mexico!

  5. 5 peregrina feminina December 30, 2009 at 10:31 pm

    Sometimes I think you are reading my mind! Great info and we must discuss this subject more whenever we finally get a chance to meet up!

  6. 6 Elizabeth December 30, 2009 at 10:57 pm

    Very thorough post, I’ll be sure to forward it to US citizens who ask about Cuba.

    I did it in 2002 before passports were mandatory for Mexico. It was straightforward: fly into Mexico using passport, then use drivers license for exit/entry from the country to Cuba. Cuban immigration was considerate of our passports and stamped a piece of paper to put in our passports instead.

    Even w/the hassle of getting to and fro, Cuba remains one of my favorite countries out of the 2 dozen I’ve visited.

  7. 7 Anil December 31, 2009 at 3:39 am

    Excellent and very informative post. I’ve read others on Cuba that weren’t as straightforward. Wondering what happens if US Customs finds out you were in Cuba?

  8. 8 spunkygirlmonologues December 31, 2009 at 11:02 am

    Great post. I knew there would be a way for American’s to get into Cuba. I was there a couple years ago and loved it. Although there was a lot less excitement involved as I’m Canadian.

  9. 9 john December 31, 2009 at 11:19 pm

    A few corrections
    it is very easy to obtain the Tourist Card at say Cancun airport. takes 5 minutes and in fact is where most travellers(not just thise from the land of the unfree) obtain them.
    To imply that you can bribe Mexican immigratins agents as a matter of course not to stamp you passsport is misleading – theer are probably more reports of refusing to accept the bribe as there of acceptance. What is more relevant is that the probability of a problem arising on your return to the USA with the double stamp is miniscule. It is several years since ANYONE has reported on any of the main Cuban travel sites any difficulty let alone a fine.
    Is the link to the Canadian travel agency very old? There is lots of misleading info. not the least being the comment that USD dollars is the currency used everywhere when it has been many years since that was true.

    • 10 laurenquinn January 1, 2010 at 12:59 am

      Thanks for the added info. I should have clarified—I’ve heard of people having difficulty getting a tourist card at the Havana airport, not the Cancun. As to the double entry stamp, I remember it being an issue that came up a lot in the chat rooms and forums during the time of my trip. It’s probably more of a paranoia thing than anything else—I’ve never had my passport inspected upon returning from a trip. But alas my travel companion was a bit more skittish than me about these things, so we went for a bride, and it worked. But it was probably just as risky, if not more, than getting the extra stamp. Thanks for the updated info.

      Dunno about the Canadian travel agency. It had a fairly high page ranking, which would leave me to believe that at least some of the info on the site in current. But I meant to use it more as an example of what not to do. Cuba’s been on the CUCs for hella long, so that’s some seriously outdated info…

  10. 11 Don Flan January 2, 2010 at 12:32 pm

    Thanks for the lowdown. The book “Walking to Guantánamo” should also be of interest to readers.

  11. 12 Julie January 2, 2010 at 6:08 pm

    I’ve made the trip about 8 times and everything you say here is spot on. Very best gateway in my exp. is Cancun.
    I’ve written couple articles about the same subject:



  12. 13 laurenquinn January 3, 2010 at 12:31 am

    Thanks Julie! Loved your posts.

  13. 14 Jay January 11, 2010 at 12:44 pm

    Hi Lauren,

    Thanks so much for your posts. I’m going to Cuba next month w/o official sanction and have had a lot of trouble finding reliable info.

    I do have one question. When you bought your ticket to Havana from Mexicana, what payment method did you use?

    • 15 laurenquinn January 11, 2010 at 12:54 pm

      I just used my credit card. The charge appears as “Mexicana,” and doesn’t list the actual flight info. I suppose someone could search if they really wanted, but does Customs really care that much? My thought is no.

      One word of caution though: a friend just came back from Cuba. She went through Cancun, and a friend of hers decided to join her in Mexico last minute, thinking she could just buy a ticket to Havana in Cancun. It was over $800! For a 40 minute flight! That’s for peak New Year’s/Anniversary of the Revolution season, but still. Yeesh! Gringo tax? Perhaps…

      • 16 Jay January 12, 2010 at 11:12 am

        I’ve heard about this strategy of using your birth certificate and driver’s license to enter Mexico from the US (supposedly this will suffice), and then using your passport to re-enter Mexico from Cuba (which I understand is required). That way you end up with just one Mexican stamp. Although I do wonder how many days you’d need to allow between the Cuba-Mexico flight and the Mexico-US flight. Maybe one day would be enough. “Hey, we just went down to Mexico for one night to party” (or whatever.) Any thoughts?

  14. 17 laurenquinn January 12, 2010 at 2:10 pm

    I’m fairly certain Americans need a passport to enter Mexico these days. There’s some loopholes for minors and people on cruise ships, and in border zones. I’ve always just brought my passport to Mexico, assuming it was easier than figuring out what kinds of alternative id is accepted.

    The method you described might work, but I say don’t overthink it. Just go, be slick and try not to worry too much; the vast majority of people encounter no problems at all.

  15. 18 Jay January 13, 2010 at 12:28 pm

    I probably have been overthinking it. I’m just gonna suck it up and go. BTW, I talked with a lawyer who’s very involved in the Cuba issue, and he said there’s been no enforcement of the travel restrictions since 2006.

  16. 19 Eddy February 8, 2010 at 1:10 pm

    How much would be sizable peso?

    • 20 laurenquinn February 8, 2010 at 1:14 pm

      Honestly, I don’t remember. I imagine it would have been akin to $20. But judging from more recent feedback, I don’t think the double stamp is as much of an issue these days, so it might not be worth risking the whole bribery thing.

  17. 21 Eddy February 8, 2010 at 1:15 pm

    I believe there are flights from Monterrey and Mexico city as well. Would it be better from these cities so not to raise suspicion instead of Cancun? Thank you so much.

    • 22 laurenquinn February 8, 2010 at 1:17 pm

      Maybe. I personally think they’d be much nicer places to stop over in than Cancun. But I really wouldn’t stress on it too hard. Good luck!

  18. 23 Eddy February 8, 2010 at 1:24 pm

    …I was saying that is because I am planning to take the Bus to Monterrey ($40) (8 Hours)and flight from there to cuba. It’d be much cheaper If everything goes ok. What if a person has a dual citizenship? Can one use the other passport and avoid a the double stamp entry? Thank you for all your help.

  19. 24 laurenquinn February 8, 2010 at 1:29 pm

    Sounds like a good plan. Using a different passport would probably be a good idea too.

  20. 25 Eddy February 8, 2010 at 1:38 pm

    I guess I’ll post to let you know how it went.

  21. 26 John McAuliff February 16, 2010 at 9:18 am

    President Obama has the power to make it much easier for educational, cultural, religious and humanitarian travel, and there is a suggestion he might finally be moving in that direction:


    For conventional tourism, Congress must pass the Freedom to Travel bills so please tell your Representative and Senators how you feel about regaining a fundamental human right.

    As noted above conscientious non-cooperation is another option as the Cubans do not stamp US passports and tourist visas are available from inbound airlines. Lawyers say that for at least two years no one has been sanctioned by the US government who traveled through a third country without a license.

    Cancun is especially convenient because of an evening Mexicana/Click flight, but connections can also be made daily from Cayman (book tickets on Cayman Airlines web site), Nassau, Jamaica, Panama and Canada (especially for all-inclusives).

    John McAuliff
    Fund for Reconciliation and Development
    Dobbs Ferry, NY

  22. 27 Jay March 8, 2010 at 3:01 pm

    I’m an American and went to Cuba for nine days recently. I had been concerned about coming back through US customs, but let me tell you — it was a complete non-event. I connected through Cancun and there were hordes of Cancun tourists going through customs with me. I spent all of 15 seconds with the customs agent — he looked quickly at the first page of my passport, scanned it, stamped it, and sent me on my way. The Mexican double-stamp is not really an issue.

  23. 28 Delia Harrington August 25, 2010 at 11:45 am

    don’t worry too much about customs–they may question you/confiscate items, but the “travel ban” is, as you mentioned, an economic issue. i have it from the US Special Interests section (equivalent of American embassy in Cuba) that it is entirely a Treasury issue, and no state dept or border officials will punish you.

    as for the money, you can get a Carribbean Transfer Card which will work like a debit card down there, if you don’t want to travel with all that cash. you took 1300? how long were you there for? i spent a bit less than that and lived in havana for three months.

    also, if you have friends in cuba, especially ones with social cache, have them meet you at the airport. they may be able to come bring you in and speed up the customs process

    good guide, very thorough!

  24. 29 Marcelo January 7, 2011 at 7:17 pm

    Hi. Amazing post. Really got a lot out of it. Thanks. I was wondering if you’ve heard of people making the x-fer to Cuba via Panama City and if there are any issues involved with that?

  25. 30 m ponce March 22, 2011 at 8:36 pm

    What if you travel florida to jamaica to cuba,then return cuba to cancun to florida…..does that get rid of the double entry stamp?

    you can just make it seem that you traveled to jamaica straight to cancun and then back to florida.

    any suggestions from anyone?

    • 31 laurenquinn March 22, 2011 at 8:41 pm

      I think that would work—but be super expensive. One-way flights are costly. Plus you’d have to arrange a lot of it yourself, because a US-based travel agent wouldn’t be able to help you. I say just fly through Mexico. You’ll be fine. 🙂

  26. 32 Malinda August 8, 2011 at 2:55 pm

    Short, sweet, to the point, FREE-exalcty as information should be!

  27. 33 Michael February 29, 2012 at 7:07 am

    Is there any problem with people leaving Cuba? Do people ever get stranded there?…And even though it doesn’t seem like the double stamp is an issue, what happens if they catch that?, I am trying to obtain as much info on traveling to Cuba before I make any plans. Thanks!

    • 34 laurenquinn February 29, 2012 at 7:20 am

      I don’t see how detaining people would benefit the Cuban government or tourism. But I really don’t know… In terms of the double stamp, I’ve heard of some immigration agents just letting it slide, or of people being pulled aside and searched, and once every few years, someone’s made an example of. But the chances seem pretty slim.

      No te preocupes!

  28. 35 Emily April 25, 2012 at 8:45 am

    Hi all! Thanks for the advice! Just came back from 10 days in Cuba and got a little nervous about the re-entry issue. Turns out it was no big deal! We flew from Santo Domingo, Dominican Republic into Havana using the the Cuba Travel Network to purchase the flights and rent a car. Had no issues with their services–everything worked out perfectly! I had four stamps in my passport (2 entries and 2 exits from Santo Domingo) and couldn’t convince the customs people to not put the stamps in. I was a little nervous because it was a new passport so they were the only stamps in there! Flying into Los Angeles, I had 4 different people look at my passport–and no one said a word about my stamps! I of course didn’t volunteer I had been to Cuba, but I just want to reassure all the travelers that are nervous like I was that it’s nothing to worry about! Obviously if they really wanted to enforce the “travel ban”, they would stop us all from being able to purchase flights online. I paid for the flights and car by credit card online and brought 2,000 dollars in the form of Euros. To my surprise, after 10 days of traveling and staying in case particulars exclusively, we came back with about $700 left. We had a blast, met some amazing people and heard incredible music. I would highly recommend the trip and look forward to going back! Cheers!

  29. 36 Vani September 18, 2012 at 3:47 am

    Hi there!
    I have tickets to travel to Cuba this week via Mexico City from LAX…I am so scared I want to cancel the trip! I am traveling by myself and meeting friends from Spain in Cuba. I am a legal resident here and I travel with my passport from Argentina and my greencard. I am nervous about US customs finding out and being deported or fined…
    Anyone here traveled to Cuba with a similar legal status?
    Thanks, this article makes me a little more relax!


  30. 37 markkligman October 31, 2012 at 7:10 am

    Hey, just came across your blog and I’m really digging your Cuba posts. I just got back from an 8 day legal trip. It was amazing, but I definitely need to go back now by myself. I’m writing about it if you’re interested:


  31. 38 Ninha January 7, 2013 at 3:29 am

    I just came back from Cuba yesterday. I’m a green card holder and my Husband and my son are U.S citizen.
    We went to Cuba through Mexico City and came back through there too. When we got to Mexico they stamped our passport again. I freaked out because the guy there stamped mine on the same page it was stamped for the first entrance.
    My husband and I had already planed to say that we went on a cruise from Mexico, but there is no way to say we came back from a cruise to Mexico City. We were very worried, and diced to play dumb if anything happened.
    Luckily, the immigration office who checked us was planning to go to Brazil (my homeland) and all he asked us about was where and when to go to Brazil. Did not pay much attention to our passport.

    I noticed that for green card holders it is pretty easy to just say that you went back to you home country as an explanation to the 2 entry stamps from Mexico (my aunt did that). If you have 2 passports, you just have to make sure you get stamp on the one that is not American, which I should had asked for my son. Problem is, thanks to the U.S, Mexico now require visa to Brazilians, the only exception is if you can prove that you can get to the U.S. legally. We didn’t ask to get our son’s brazilian passport stamped instead of the american so it wouldn’t look weird that me and my husband had 2 and our son had 1 stamp.

    If you are going to Cuba you should bring some stuff to give to them. They really appreciate soap, shampoo, conditioner, tooth past, etc all hygiene products, as our guide said “when you have to choose between buying a chicken or buying soap, its a no brainer”. Bring clothes that you don’t use anymore or that your kids has grown out of.

    We will definitely go back. But this time we will go through one country and out through another, just so we don’t have to worry about stamps..

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Lauren Quinn is a writer and traveler currently living in Hanoi. Lonely Girl Travels was a blog of her sola travels and expat living from 2009 to 2012. She resides elsewhere on the internet now.

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