How to Travel to Cuba Without a License

Travel Guide to Havana Cuba


Cuba is an amazing country with an amazing history of music, wonderful people, and beautiful beaches and cities. It is unfortunate Americans can’t travel there easily. This is a guide on how to travel there without a visa issued by the United States (which is what I did). Of course there are ways to do it legally but it takes more time, money, and resources to make that happen. We can only hope this administration will open up travel to Cuba but until then it is a great adventure to travel there “illegally.”

A Little Background about Cuba

It is legal to travel to Cuba but it is illegal to spend money there which is due to the trade embargo. The US State Department will allow anyone to travel there legally but you will need to fall into certain categories such as being a journalist or traveling for educational purposes. This means you will need to apply for a license and be pre-approved for travel to Cuba. Most of us wouldn’t qualify for this which is why thousands of people every year travel to Cuba illegally from the US.

More of my Favorite Travel Photos from Cuba

Old Havana

More of my Favorite Travel Photos from Cuba

People-to-people tours are becoming very popular and basically allow you to skirt around the travel laws. They are tour companies that get you into Cuba for an organized tour with an agenda. There are a few set things and they arrange the flights and hotel. This allows anyone to side step the embargo. There are plenty of these companies online and they are not cheap. This guide will teach you how to do it without a visa issued by the US.

How to Travel to Cuba from the US Without a License

1. Fly through another country such as Canada or Mexico. I recommend Mexico since flights from Cancun are cheaper and quick. You could also fly from any other Central American country or somewhere else in the Caribbean. Some people have reported being questioned upon reentry through Canada as an American citizen. Those chances are low and Mexico was a cheaper and more direct option for my travel. Others use Panama City, Panama as the third party entry point but just do whatever works best for your itinerary.

2. Purchase a flight to Havana from the US. Keep in mind sites such as Kayak and Orbitz will NOT have flights to Cuba. Many airlines will fly there such as AeroMexico and Cubana Air. There is no possible way to book a commercial flight to Cuba at this time with online booking agents in the United States. All flights through organized tours are arranged through third party tour operators. Even if you have a legal visa for travel, Kayak will still now show you results for flights to Cuba.

Travel Hacking Tips

I flew the first leg of my trip to Cuba for free using miles. I flew into Cancun before departing to Cuba a few hours later.

However, you can book a flight online with non-US airlines. is a great place to start looking for flights. They booked me on Cubana and the customer service was great even when my flight was rescheduled.

Cubana Air

Cubana Air

Flights range from $275-375 roundtrip from Cancun. Not cheap for a 1 hour flight but it’s worth it, trust me.

3. Before you leave the airport pre-purchase your Cuban visa. This ran me $25 at the Cancun airport and was easy to setup. Give yourself an extra 30 minutes to get this on arrival or between flights. There is a counter at most airports where these can be purchased before you head to Cuba.

4. Prebook your accommodation for Cuba. Some immigration officers in Cuba will ask where you are staying and you will have to fill it out on your customs sheet anyway so book ahead of time. If you want to save some money and have a more authentic stay book with a Casa Particular. They are private rooms in Cuban families homes and will run you $25-35/night.

Old Havana Cuba

Many forums will say Casas are not acceptable housing for visitors but this is not the case. I did not pre-book a hotel and had no issues at immigration. Just be honest with the officer. They want Americans to come and there is no need to hide it. They are going to see your passport anyway :)

See my guide for where to stay and how to book a casa particular.

Note: Some Casas will arrange an airport pickup if you ask. This makes life easier on arrival and will run you $20-25 USD to get downtown Havana.

Transportation in Havana on arrival. He spelled my name wrong but close enough.

Transportation in Havana on arrival. He spelled my name wrong but close enough.

5. Cuban Immigration and customs is pretty straight forward. They may ask where you are staying, how long, and why. They are happy to welcome Americans so no need to lie. They will NOT stamp your passport so don’t worry. They will stamp your visa so don’t lose the other half they give to you for your exit.

They actually did not stamp mine correctly on the way in and when I departed it took about 30 extra minutes for them to sort it out. There were no issues of course and honesty is key here.

Cuba Immigration Forms

Official forms to fill out for customs and immigration in Cuba

6. Bring a lot of cash. Your credit cards will not work anywhere in Cuba. If you run out of money it will not be an enjoyable experience. Plan your expenses well and then bring more on top of that. You want to be prepared. There are two currencies in Cuba, the Cuban convertible peso, for tourists, and the peso, for the Cubans. You will use the convertible (CUC) everywhere in Cuba so no need to exchange money for the Cuban peso unless you want to collect some unique currency (which I did to bring home).

It is very easy to exchange your cash but don’t expect a good rate. Basically the Cuban convertible is about 1:1 with the USD but there are fees to exchange it on top of the exchange fee. A nice hotel in town is an easy place to convert the cash just don’t expect a great rate. Some people recommend exchanging your USD to Euros before you leave to get a better rate. That is up to you but was not a concern for me.

Old Havana

7. Leaving Cuba. Don’t forget the other half of your visa when you return to the airport. Just keep in in the pages of your passport for safe keeping. They will stamp it and take it on the way out of the country.

It is just like any other international flight so no need to worry. Two hours prior to take off is plenty of time. They forced me to check my carry-on but was able to bring my backpack on the plane. Just be sure to take all valuables out of your luggage if you are forced to check your bag.

8. Reentering the US. Remember you are not the first or the last person to travel to Cuba without a license. Thousands of people do it every year. Do NOT list Cuba on the “countries I have visited” part of the immigration form in the US. And when the immigration officer asks just say Mexico or whichever country you just came from.


Now, I do not recommend lying here but when they ask, “where have you been?” you can honestly say Mexico. Do not include Cuba. Some people have reported on forums they mentioned Cuba and had no issues but I do not recommend this. It is possible to still be fined heavily for traveling there and there may be additional questioning if you mention your trip to Cuba.

This was a much more straight forward process than I imagined and 100% worth it. I will return again some day with or without a license from the US.

Other Notes

The Mexican Death Stamp

If you read enough on the forums you may hear about the “Mexican death stamp.” This applies to any third party country but was named for Mexico since it is a common departure country for Cuba. This process can make anyone a bit nervous until you realize you have nothing to worry about.

Here is how it works:

When you fly into Mexico you receive an entry stamp in your passport as you would in most countries. You then proceed to Cuba where you get no stamps at all. You then fly back to Mexico and receive another entry stamp. This means you now have two entry stamps into one country(Mexico) with no exit/entries to any other country. If you were to line up the dates of the stamps in your passport it would be clear you were somewhere for a period of time with no record of it. A curious US immigration officer may notice this or question it but most likely will not care at all. Seems like this could be a problem right?

My Experience:

I read on most of the forums when I was doing research that this was a non-issue but just based on the name of the it I was slightly concerned. Some suggested bribing the Mexican officer with a $20 and politely asking for no stamp but I didn’t take that route.

When I first entered Mexico I asked in Spanish for the officer not to stamp my passport at all and failed. My Spanish is ok but the officer could not have cared less and stamped where he pleased.

Old Havana Cars

I then tried again when I entered the second time. This time he responded in English that he has to stamp it by law. Of course I knew this, but so many border officials around the world will look the other way and have for me in the past. I then asked if he could please stamp a different page from the first stamp to separate the two. The officer nodded (what seemed like a yes) but put the stamp right next to the first one (just doing his job I guess).

My passport was 100% full with new pages sewn in. I was hoping a couple stamps mixed in with all the other stamps would be hard to notice. He found one of my brand new pages I just put in and put them side by side.

At US immigration in Atlanta I didn’t mention Cuba or write it on my form at all. The officer looked at the stamps and said welcome back. There you go. Don’t worry about it. It was like any other return home. Where did you go? How long were you there? Thank you, stamp, move on.

A way around the US checkpoint

The US is rolling out the Trusted Traveler Program to more US cities this year. In Atlanta, had I applied for this, I could’ve bypassed some of this interaction all together. This will cost you $100 to sign-up and you must pass a screening process but if this is something you plan to apply for anyway it is great for return travel from Cuba. Just be sure to make your connection that has Trusted Traveler.

What can you bring home from Cuba?

If you go down as part of a people-to-people tour or any other legal way you are permitted to bring home art, music, and anything along those lines. You cannot bring back Havana Club Rum and Cigars. Chances of getting searched are low when you get back to the US but if you are trying to bury the evidence don’t bring back anything at all. This means currency, paperwork, ticket stubs, maps, guide books, or anything else that proves you went there.

However, I brought a few things with the help from some friends in Mexico. I always bring home currency and since Cuba has two currencies I couldn’t leave it behind. Along with some cigars and some artwork I picked up in town. All small enough to not raise any alarm entering the US but the risk is up to you. I don’t recommend it.

Cuban contraband

Cuban contraband

What to Remember For Your First Trip

Relax. Thousands of people travel to Cuba every year illegally and have no issues at all. There are reports of people being fined up to $10,000 or more or lesser fines of $2,500. This is rare and I wouldn’t worry about a fine. Also, if you don’t speak Spanish make sure your Casa Particular owner speaks English or you may find life difficult in Cuba. All of the major hotels will speak English but be sure to establish communication in English with your Casa before you leave. This way when you arrive you won’t have any communication problems. My casa owner spoke 100% Spanish but that just made it more fun and allowed me to practice my Spanish.

Important Updates for Americans Traveling to Cuba (Updated Dec. 17, 2015)

In a historic announcement, President Obama announced Cuba and the United States are restoring diplomatic relations.

What does this mean for U.S. Travelers to Cuba?

The U.S. is planning to open an embassy in Havana in coming months. This is big news for Americans in Cuba who lose their passport or face an emergency abroad.

Normalizing Banking and Trade

Previously U.S. credit and debit cards did not work on the island. With the changes today American credit and debit cards will work in Cuba. This is big news for travelers because they no longer need to rely on cash for their trip.

I had to rely on cash during my time in Cuba. This can be dangerous for many reasons and you run out of cash in Cuba (while there illegally) it can be a problem. Even for legal travelers this will make life easier.

Will Airlines from the U.S. Fly to Cuba Now?

Not quite. Obama announced his goal is to make travel to Cuba easier and make it easier for Cuban families to connect with relatives. That does not change the current travel restrictions for Americans. The only legal way to travel to Cuba is through People to People tours or by applying through OFAC.

Bringing Back Goods From Cuba

This is one of the biggest changes. Cuban cigars are no longer banned!

Now all licensed American travelers to Cuba will now will be able to bring back $400 in Cuban goods to the U.S. This includes tobacco and alcohol products worth less than $100 combined. The ban on cigars is over and great news for cigar aficionados.

What’s Next for Cuba Travel?

While Delta and American haven’t opened up airfare on Kayak just yet this does give Americans hope. Of course there is always the people to people tour but it would be nice to travel there freely, just as we do to any destination in the Caribbean. The next few months will be exciting to watch as diplomatic relations hopefully continue to improve.


Legal Travel to Cuba

There is a lot more information about this readily available online. Essentially you need a “people-to-people” license issued from the US. You can go with tour companies or in groups depending on what your travel is for. Journalism, educational and religions purposes are just a few of the ways you can gain entry through application. The benefit of this is you can leave on a chartered jet from a few different US airports. These flights are off limits to ordinary people who don’t have a license.

The negative side of these tour groups is they are usually more expensive and a lot more structured.

Go to Cuba before the US invades (with tourists) and have fun! Drink where Hemingway sat, watch a Cuban béisbol game, and smoke cigars on the Malecón! It is a beautiful country and now one of my favorites. It is not to be missed!


  • Ryan

    In regards to max expenses between legal vs illegal travel to Cuba. If you take into account the time value and cost of having to travel to a different country before flying to Cuba / the risks of traveling with only cash/ and the ages of the general demographic that’s looking to travel there… would you say that maybe trade off might be a little more favorable to traveling legally?

    • Clint Johnston

      Thats a great question. In my experience I used miles to get to Cancun (which is generally an affordable flight anyway) and from there flew over for less than $300 RT. I had no time restrictions in Cuba and was able to stay with a Cuban family which is also very cheap. If you were to take the people to people tour, which is gaining popularity, you have a more fixed schedule and limited time in the country. P2P tours usually start at $1000 and go up from there. Personally, I would choose the “illegal” way since you have more freedom and I think could spend less money over a longer period of time with careful planning. However, it all depends on what you are looking to do there and your comfort level.

  • http://none F. Olmo-Pandiella

    I will love to go to Cuba, my grand parents are (ware) from la Havana, I born in Spain, became (mistake number one) US citizen, would love to go, I know a Cuban family (sure could stay with them) would rather do it legally.
    Question: Is religious reason good for the Department of Treasure?
    Can I get a ‘visa’ or ‘permit’ under that category?
    any suggestion are welcome


    • Clint

      There are a lot of great legal options with people-to-people tours. You can google these to find some options. If you want to go without a tour then you will need a license as you mentioned. You can travel there for religious reasons but it is not as simple as just saying that. You will need to apply and it can be difficult for them to accept. Another option is a “general license” but you will still need to prove why you are going for a valid reason. You can apply with OFAC and see if you can get a license the legal way. Go to their site here and it will give you more information on how to apply. Good luck with your trip!

  • http://none F. Olmo-Pandiella

    Thanks Clint

  • Leon

    Great post! I’m considering going to visit Cuba this month and your post really covered all my concerns. Much appreciated! By the way what would you say is a cant miss experience there?

    • Clint

      Thanks, Leon. The highlight of my trip was staying in a casa particular instead of a hotel. I stayed with a wonderful family and they recommended all of their favorite spots in the city. I mentioned some favorites on the Huffington post recently if you want to take a look at it there.

  • Judy Lagoa

    Hello! I just stumbled across your post while researching and wanted to ask you a question… I am not from the US but from Germany and I have to write a paper on the US/Cuba travel restrictions. Weren’t the travel restrictions put in place because of political reasons such as not wanting to support the Cuban regime? Is it not unethical to travel there illegally just to please oneself’s desire for travel, not particularly caring for the Cuban people’s situation in the long run or at all? I am not asking this to offend you but often the information to be found online is very… one-sided and I was hoping you had a different point of view on this and could offer me a new insight! I would really appreciate it if you took the time to reply!

    • Clint

      Hi Judy, great question. Well this ban been in place since Fidel came to power in 1960. And yet 400,000 Americans traveled there last year alone. The US is second behind Canada in visitors to Cuba. Travel has always been permitted to Americans who applied as journalists, academics, those with family members on the island and government officials. And now the people-to-people tours allow all americans to travel there with these programs. Traveling there illegally is no different than traveling there on one of these tours except that you have more freedom and lower costs. You may even help more locals by staying in homestays and not the mega-resorts Canadians and Europeans fly to every year.

      In my opinion is not selfish to travel to a country like Cuba out of curiosity for travel and simply due to an embargo most Americans want lifted. You could make a case for countries all over the world that we could not travel to. Should we also avoid China based on their human rights record, Saudi Arabia on their views towards women? There are problems are found all all over the world. Maybe the best way to make a change is to bring more attention to the problem by exposing ourselves to it.

      Hopefully that helps and feel free to ask me anything else. Thanks

    • L Cavendish

      Curious if the figures count multiple trips by one person as one American or the number of trips. Also…wonder if US residents (Green Card Holders) are considered as Americans when they arrive there.Say a Cuban with a green card? Just curious.
      When a legal charter flight from US arrives…are all people on board counted as Americans since they arrived from America? Not as crazy as it sounds.If so…150 people/flight…73 flights per day…365 days…not impossible.
      Saudi does not have tourist visas, BTW.

    • Clint Johnston

      That’s a great question. I pulled that from an article on the topic and I will try to locate it or find another one. It does seem very high now that you point that out. My best guess it that figure was meant to represent the number of the past x-amount of years.

    • Clint Johnston

      Here is another article with some stats:

      “Just over 98,000 U.S. citizens visited Cuba in 2012″

      “The numbers do not include more than 350,000
      Cuban Americans estimated by travel agents and U.S. diplomats to have visited the island last year. Because Cuba considers them nationals, they are not listed in its tourism statistics.”

      I guess it depends how you categorize the US tourists?

  • Kelly

    Thanks for this helpful article. What would you have said to Immigration if they asked you why you had 2 Mexican departure stamps?

    • Kelly

      I’m sorry – I meant to say two Mexican ARRIVAL stamps. Not departure.

    • Clint

      I would probably have been honest with them. I have read of people who were completely honest and told them they went and had no issues. However, you could be stopped for questioning or even face fines. That said, thousands of Americans travel to Cuba like this every year so the risk is low.

  • Jhorner

    I read this and all is good, however, there is one more thing. I was born in Cuba. I am an American citizen. My passport has Cuba as my place of birth. Is there any danger of Cuba not letting me out? Or any other things I should worry abnout?

    • Clint

      You can legally go to Cuba to visit family. You would qualify for a license and wouldn’t need to travel there illegally. It states, “a person with family in Cuba can visit their family for an unrestricted period of time” and you can read more about that here. Hopefully that helps and good luck.

  • jhorner

    No family, I was born from Americans working overseas.

    • Clint

      Ok, misunderstood sorry. That is a bit more complicated I suppose. I would have to look into this more but since you were born to Americans overseas I don’t think you would have issues. However, it only takes one confused immigration officer to pull you aside in Cuba. I would inquire with a people-to-people tour. Even if you do not intend to use their legal services simply explain your situation and they should be able to help.

  • Ken

    Thanks for the great article, Clint.

    I’m a U.S. citizen now living in Korea. Recently been planning to fly from Seoul to LA to Mexico City to Havana (that’s the fastest way!). I’ve had the same concerns as you all along, whether to travel there with or without a license, and searched all possible options. But quite honestly, the way to get the license is way too complicated, and takes too much time to take risk for.

    A couple of questions on going to Cuba from Mexico City (although I read you went through Cancun, I was wondering if you could shed some light).
    1. Do they have U.S. customs preclearance at MEX airport? Based on my research, most likely there ISN’T one.
    2. Can you buy your travel visa directly from MEX airport?

    Thanks for lifting worries of so many of us.


    • Clint

      Thanks, Ken.

      I agree, acquiring a license is difficult and most of us would not qualify for them anyway meaning we would have to pay for the overpriced people-to-people tour (only other legal option) to get in unless of course you plan to go in from Mexico City as planned.

      I don’t think Mexico City has preclearance based on my research either.

      However, you should be able to buy the visa on arrival to MEX. That shouldn’t be a problem. Just ask your airline at check-in and they can help you out.

      But sounds like a great trip and is is definitely worth it. Let me know if you have any other questions.

  • Arya

    Thanks for all your insightful information. It has been great help planning out a trip to go this summer. I have become comfortable with the situations explained by you and other blogs ive read across the internet. My only issue is I’m not sure how to go about going to Cancun and immediately leaving to Cuba. I will most likely go on one of the daily Cubana flights that leave at around 1:10 PM each day and will surely buy my ticket in advance through one of the sites you mentioned. I would fly straight to Cancun (arriving on a flight somewhere between 10am to 12pm. My question for you is would this be enough time to transfer flights within Cancuns international airport?? I want to spend a few days in Cancun on my way back, but want to immediately go to Cuba on arrival. Would it be a better idea to spend at least a day in Cancun in case of a possible flight delay?? I have read on some places the Cubana flight to Havana is almost always delayed, so if I get in on a flight that arrives in Cancun at 10am i should have ample time to catch my flight, buy a visa from the airline, etc. Another question, would it be smart to only bring a carry on for quick transport from flight to flight?? sorry i am asking so much, any info and knowledge is appreciated!!

    • Clint

      There is always a chance your first flight is delayed and I would recommend at least two hours between flights. You will have to go through customs in Mexico and probably switch terminals so the more time the better. If you arrived at 10am you shouldn’t have any issues catching a 1:10PM flight that same day. Even at 11AM you should be ok but any delays on the first flight could really cut it close. Three hours is probably best between flights if you want to be safe. I think you should be fine with a same day departure to Cuba when you arrive in Cancun. Just be sure to try to get in as early as possible.

      I only brought carry-ons into Mexico which will save a bit of time but not too much. The longest wait is going through immigration and getting to the front of the line. That line has taken me 45 mins in many cases but as little as 15 mins other times. Once you pick up your luggage to go through customs it is pretty fast. However, the Cancun airport has the red light/green light button that you press when you leave. The rare red light simply means they search all of your luggage and it will add another 5-10 mins to your transfer time. Depending what terminal you arrive in it may take about 15 mins to get to the other terminal. I always recommend carrying on your luggage, however Cubana forced me to check a very small carry on and only allowed my backpack on the flight.

      Good luck and feel free to ask any other questions!

    • delia

      I will never forget the time that I missed xmas day with my family in NJ because I was coming back on xmas eve from Cuba. My flight from Havana to Cancun was originating in Santiago and wound up being 8h delayed. I missed my connection in Mexico and wound up not being able to get back until 24h later. :-( Now I make sure to ALWAYS book an extra night in Cancun on my way back home. Cubana flights are notoriously late, so at least make sure you have a huge buffer.

  • Ken

    Hey there Clint.

    Thanks for the reply and additional insight.

    I seem to need your opinion once again:
    What do you think about flying to Havana from somewhere that DOES have US preclearance? Like Nassau (Bahamas) for example. Would they grill you with questions? How would you answer them? Would you avoid going via such place at all?

    Thanks always, and hope you have some meaningful trips this year as well.


    • Clint

      Hey Ken,

      Third party countries really don’t have an interest in where you travel as an American. However, it is always best to eliminate additional encounters with officials. I do not think you would be grilled with questions but I am only speculating. In the research I have done the only immigration officer you should worry about at all is the first one you meet in the US and even then they don’t ask many questions. The questions are always basic no matter where you are returning from and you shouldn’t expect it to be a much different experience returning from Cuba. Hope the helps.

  • Ellen

    Hi Clint,

    Thanks for the great info. I am planning to go to Cuba with a friend for her birthday from May 20 – May 25 (next month). We have reservations to Cancun as well as a place to stay in Havana. I planned my flight around getting to and from Cancun based on the timing of the Cubana flights, leaving a lot of time inbetween. I am still trying to reserve the flight from Cancun to Havana on Cubana Airlines and on their info page, you have to put your passport number. I’m nervous about doing this so I haven’t reserved yet. Do you think it’s a problem to write down our passport numbers? Also, I was just gonna do it on line on their website. Do you know if it will be ok to do it that way and pay with a U.S. credit card? I contacted a travel agency and it’s more expensive (of course) to go through them. Thanks a lot. Any info would be appreciated since I want to get the Mexico – Havana flight secured.

    • Clint

      Hi Ellen,

      I booked my flight directly through Cubana Air on their site as well. I used all of my real info when booking the flight without any issues. I also used a US credit card without any problems. You could work around the US credit card problem by using a prepaid card under another name (a friend or family perhaps) but I don’t think it is necessary.

      I would recommend simply booking with your info and card. If that makes you feel uncomfortable simply use a friends card, who is not traveling, and book with their card. You could always order a prepaid card card and use that but I wouldn’t stress about it too much.

      Feel free to email me with any follow up questions and have a great trip!

  • Coleen

    Great information! I was wondering if you have to worry about any repercussions about traveling to Cuba after you’ve returned to the US without incident. What I mean is that you’re posting an article stating that you, an American citizen, traveled recently to Cuba and have posted pictures proving it. Is it possible to be charged/fined after the fact based on a blog post/ pictures on the internet?

    I’m contemplating going to Cuba in August and while I can leave pictures off the internet, I do like to share travel photos with friends.

    • Clint

      Hi Coleen, I haven’t had any issues with my travel to Cuba. Americans can legally travel to Cuba if they choose to pay for a people-to-people tour. If you were to travel there illegally and then post photos from your trip when you return it would probably be difficult to determine how you traveled there simply by the photos. If you are just sharing them online with family and friends I wouldn’t worry too much about it.

      It is definitely worth the effort and if you don’t feel comfortable going illegally there are legal options you can explore.

  • Alison

    Hi Clint!

    Just stumbled across your site. Thanks for sharing your experiences – I’ll be following you.

    For other readers interested in Cuba travel, I’ve been there several times, including 8 weeks last summer w/ my then 5 and 8 year olds! I usually book the Mexico-Cuba portion of my travel through or with no trouble and pay w/my credit card. i have found the prices to be reasonable, not that much more than I pay if I purchase my ticket cash at the nearest mexican border airport. I do have to scan and send them some documents however since I don’t have a European credit card. I fly through Mexico City which is easier for me than Cancun. I have also found AeroMexico to be cheaper than Cubana. There is a new Mexican company, Interjet, that also flies to Havana. AM still works better for my situation however. I spend the night in Mexico City since I don’t have much of a layover to get the visas, and if the flight is late, I’m screwed anyway! I try to simplify a bit w/the kids.

    I have never had any trouble with my return to the US, but I admit to having a certain level of anxiety, which I might have travelling with kids anyway! I now fly back to a Mexican border city and cross the border to the US since I live very close to Mexico and it’s actually cheaper than the other options. .

    I love Cuba, as do my kids! The logistics of getting there can be stressful, but definitely worth it. It is not always easy, but we have had incredibly moving experiences. Taking off end of June for a four week stay! We can’t wait!

    • Clint

      Hey Alison, Thanks for sharing your positive experience. It sounds like you have this method down and are doing it with kids too! AeroMexico was cheaper I agree with you but last year they cancelled many of their routes to Havana from Cancun. My flight was actually cancelled and I was put on a Cubana. Flight was still reasonably priced in my opinion compared to tour operators.

      A agree that logistics can be stressful but its people like you who put others at ease. Thanks for sharing and hopefully we can encourage more people to go to Cuba. It is a beautiful country!

    • Alison

      I’ll see if I can drop you a line from Havana! They just started faster & cheaper (4.5 CUC) internet access. Looking forward to your newsletter and seeing how I can adapt your strategies for travel w/kids. At least we all accumulate frequent flyer miles! (on AM kids accumulate MORE than adults!)

      By the way, your pictures are beautiful. Thank you!

  • jordan


    Just wondering if there could be any issues getting the visa in Mexico City or in Cancun with an American Passport? Would there be any chance of them denying me?


    • triphackr

      Hey Jordan, there are no issues getting a visa in Mexico with an American passport. It is not a concern of theirs and they won’t deny you one so don’t worry. They actually were pretty helpful in directing me to the right counter to purchase it.

    • jordan

      Thank you!!

  • Jonathan Cummings

    Clint: Thanks for the post, it’s really helpful. Quick question: how did you PAY for your flight. I’m assuming my US based credit card would not be accepted by a Cuban airline. Or.. is there a way to pay for my flight without the electronic trail? I know it probably doesn’t matter, but why risk it if you have a better idea?



    • triphackr

      Hey, Johnathan. I had the same thoughts as you and did not want to leave a trail. However, I used a US credit card to book the flight without issues and there was nothing to worry about. Originally my flight was on Aeromexico until they cancelled my flight and put my on Cubanan where I had to rebook. Again, there were no issues using my card. Cubana actually has many offices and perhaps you could contact the Canadian office and work out the details if it is a concern ( but I would not worry too much about it. I worried about a lot of things that ended up not making a difference in the end but let me know if you have any other questions.

    • Greg

      The flight to Grand Cayman on Cayman was the cheapest route for me from Miami and they book from Grand Cayman to Havana right on their site.

    • Kokopelli203

      Hi Greg, I’m considering going through Grand Cayman. Did the passport stamp cause you any problems? Did you write that you visited Cuba on your forms? Thanks!

    • GJ

      Hi there. The stamp hasn’t caused problems. I also just came back into LAX without problems. The form says “countries visited” not “all countries visited.” Best to use your judgement. Through Miami it’s a machine, not an immigration officer.

    • GJ

      *from China.

    • Kokopelli203

      great thank you!

    • Ryan

      What if someone is an U.S. citizen but also has a foreign passport? Would it be wise when leaving Mexico for Cuba use the foreign passport rather than U.S.? I am assuming you need visa for Mexico when entering back to Mexico from Cuba on your foreign passport.

  • Lucy Schaich

    My tour guide – from Australia – when asked if I could book my own flight from Cancun to Havana (saving $100 in booking fees through their company) said this: “You cannot purchase flights to Cuba directly through the airline as this contravenes the OFAC restrictions on supporting a blocked country – namely Cuba. Cubana airline is Cuban State run and owed airline so you will be billed to them which will immediately alert the US OFAC of this, and you will then be fined.”

    This seems different than your experience. I would rather book them on my own, but of course avoid the fine. Can you request that Cubana Air not list their company on your credit card bill? How did it appear on your statement?

    • triphackr

      Hi Lucy, your guide is correct in terms of OFAC restrictions, however, you don’t need to apply through OFAC to travel to Cuba. That application would get you a legal license to travel there if accepted.

      I booked my flight my flight through and booked a flight through Cubana de Aviacion directly through the site. I have not heard of anyone getting fined through purchasing a flight. People are rarely stopped when traveling to Cuba and thousands of Americans do it annually.

      This alert seems very unlikely to me but I can’t confirm it. However, I booked my flight through that site with a Cuban airline and have yet to be fined. You may be able to contact them to see what shows up on a credit card or perhaps use a pre-loaded card to make the payment under another name.

      Also, you could try to fly a different airline. It looks like AeroMexico is flying from Mexico City and Cancun again and there should not be a problem booking a flight on a Mexican airline. Let me know if you have any other questions.

  • Mike Loekle

    What a helpful article, seriously one of the most comprehensive posts/blogs/articles I’ve seen thus far.

    I was curious, do have any other resources that you could recommend regarding planning off-the-books travel to Cuba. Your article was awesome, but I figure more resources the better.



    • triphackr

      Thanks, Mike. One of my favorite sites I used researching this trip was Cuba-Junky:

      Other than that I just read a lot of travel forums.

      Feel free to email me with any questions.

    • delia

      Lonely planet’s Thorntree forum on Cuba is a fantastic resource for tons of information (though there are a lot of jerks who will make you feel bad for asking questions if they’ve already been asked before. Make sure to use the search function to at least try to find the answer before asking (and then let them know that you’ve done so if you don’t want to be flamed). I can’t think of any question that hasn’t been asked there!

  • L Cavendish

    Bahamas is also a good place to go from…if you really have to…
    Just don’t bring back:rum,cigars,animals,foods,drugs(legal or illegal)

    • Clint Johnston

      I agree. Anywhere in the Caribbean is a good place to fly from. Just depends on airfare and travel schedule. I know a lot of people use Panama City as well. I would agree it is not wise to bring anything back.

  • L Cavendish

    Yellow is a terrible color for this background…hard to see link titles, etc.

    • Clint Johnston

      Not sure what you’re seeing but links are blue and titles are black. Probably because you are using an outdated browser such as IE.

  • Travel Guides

    What a great story! Thanks so much for sharing this! Would love to hear more from you.

    • Clint Johnston

      Thanks for checking it out!

  • Missy Racho

    Clint! Amazing post, thank you! A friend and I are planning a trip in May. Purchasing a ticket from Cancun to Havana online, and thus using my card (even with a non U.S. airline, and particularly with a Cuban airline), makes me nervous. What do you think about paying cash for one once we arrive in Cancun? thanks :-)

    • Clint Johnston

      Hey Missy, that crossed my mind as well and I couldn’t find a lot of information about it. I went ahead and booked the flight with my card online. You may be able to purchase a ticket in cash in Cancun but you also run the risk of the flight being sold out on arrival. My flight from Cancun to Havana was very full. Knowing thousands of people make the flight every year as well doing the same method gave me the confidence to purchase the flight. You could, however, pickup a temporary VISA to make the purchase or just use a friends card who is not making the trip. Based on my research you shouldn’t have anything to worry about using your card to buy the flight online but I had the same questions as you before making the trip. Let me know if you have any other questions and have a great trip!

    • Missy Racho

      I purchased the tickets! yay :-) I purchased international travel insurance (health insurance) for the dates of the entire trip through Frontier (the airline I’m taking to and from Cancun). Will this suffice for the “mandatory” insurance!? thanks

    • Clint Johnston

      Nice work! They do claim to require insurance and may ask for proof but I chose not to buy it. It was a risk but next time I go I will purchase insurance to be safe. That should work for their insurance requirements. They may not ask for it but I think it was a wise decision to buy it.

    • Missy Racho

      Perfecto, gracias!

    • delia

      Aloha, Missy. I’m not sure, but I think what they want you to buy is THEIR health insurance, but from my experience, it seems that if you push it and insist that yours will cover you, they have to accept it in the end. You might want to check with Frontier’s insurance company that they actually WOULD cover you in Cuba.

  • Missy Racho

    Perfect, thank you Clint! Two more things…. first, will it be fine to purchase the tickets in advance but the tourist visa once we’re at the Cancun airport!? And second… wanna come with!? We’ll need a good tour guide :-)

    • Clint Johnston

      No problem. Yes, you can purchase the flight in advance. I picked up my visa on arrival at the Cancun airport. It was a very simply process and you can simply ask where the visa on arrival desk is when you are checking in for your flight to Cuba.

      And I would love to tag along! However, I am not sure I can swing it until later in the year. I am considering a November trip since the first half of 2014 is filling up fast. I am sure you will have an amazing time!

    • Missy Racho

      Great, thank you – I really appreciate the blog and your help! Cheers!

  • MiamiNice57

    Too Bad I’m Cuban… it is costing me $230 (2/08/2014) just for the Cuban Visa. No air fare or Hotel. To make matters worse the Cuban interest office in Washington closed down on 2/14/2014 because of the B&T bank issue although the bank said it would honor transactions through 3/2014. Guess I’m screwed!

    • Clint Johnston

      Wow. That is expensive for a visa. I know they aren’t cheap but have you considered the legal people-to-people tour option?

    • MiamiNice57

      Thank you for responding, not sure what “people to people tour” is about (but I will find out). My situation is that I was born in Cuba and we expats are considered worms “gusanos” my mother and I left in 61. My father whom died in 1976 left in 1959. We have huge restrictions from the Cuban government. Trust me if it weren’t necessary I would use any means possible to see my uncle before he passes on. He’s been in and out of the “hospital” since December of 2013, so far he’s spent the entire month of February in the hospital. We Cuban born and US born of Cuban parents are considered Cubans and stripped of our US Citizenship as soon as we reach Cuban jurisdiction (Air, Land or Sea). We had a really though time leaving the island because of the regime, now that we want to return to see my uncle we are experiencing the same difficulties.

    • Clint Johnston

      Wow this is something I know very little about thanks for sharing. I completely can understand why you would want to return but it seems very difficult with the way things are now. I hope you have the chance to see your Uncle again and perhaps there is a legal way for you to return with a particular application or license. I don’t know much about this situation but I will see if I can find any forums dedicated to the subject and send them to you. Good luck and hope all is well with your Uncle.

  • Otaibi

    If I fly from US to Cancun spend few days and then to Havana for couple of days and then to Nassau for also a couple of days before returning to US from Nassau would be a problem? I am trying to avoid the double stamps and this sound a bliss is disguised to visit 3 countries.

  • Stan

    Hey Clint i have a question recently i found out that the Cuban interest office in Washington closed down on 2/14/2014 so im still deciding whether what to do since my father ( born in cuba,is now an american citizen, his required visa is PE-11 which unfortunately isn’t available) im thinking of going through Canada and wanted to know what you would reccomend to do since I’m from New York .

  • stan

    Hey Clint i have a question recently i found out that the Cuban interest office in Washington closed down on 2/14/2014 so im still deciding whether what to do since my father ( born in cuba,is now an american citizen, his required visa is PE-11 which unfortunately isn’t available) im thinking of going through Canada and wanted to know what you would reccomend to do since I’m from New York .

  • Guest

  • BucketlistBackpacker

    Thanks for the great post Clint! I have read that if you want to visit Cuba that you need to have health insurance and that US health insurance will not work. Did you have a problem with that or did you need to buy Cuba government health insurance? Thanks!

    • Clint Johnston

      Thanks and great question. I read the same thing before I went but decided to ignore it. They did not ask for proof or insurance or proof of a hotel (another forum post I read) so perhaps I got lucky but I don’t think it is a top priority at immigration. Companies like World Nomads won’t cover you either so I decided to just go with none and it worked out just fine.

  • delia

    Aloha, Clint! You seem really nice and so I’m wondering if you or any of your readers might be able to help me with this one. I have been taking small groups of friends to Cuba for years for the most awesome life-changing dance workshops with my friends down there who are all professional dancers. The groups have always been under 10 people and really, it’s just about a group of friends traveling together and I happen to be the one who knows la Habana and the language (I even speak “Cuban” by now ;-)) In a couple of months I am planning another group, and by chance it turns out that a lot of friends of friends want to go (ie. people I don’t know so well). I’m a little nervous about liability, but I can’t imagine any American company insuring a “tour guide” who is taking people to Cuba illegally. What are your thoughts on this? If anything WERE to happen to anyone down there, would THEY even have a recourse to sue me since they have traveled there illegally?

  • Amandae Baey

    Hi, is it true i can buy tickets to Havana at the Cancun airport itself? My friend and i are flying via Cancun…CubJet is quoting ridiculous prices and routes like Cancun-Panama- Havana.Is there a reliable tour operator i can speak with?