Legal Travel to Cuba from the U.S., 2018

For over three years, there have been many changes to the regulations regarding travel to Cuba. In December 2014, President Obama announced the first wave of amendments that would make it easier for those under U.S. jurisdiction* to travel to Cuba.

Post-Trump Cuba Travel Summary:

What the Trump Changes Really Mean & My Thoughts

How to legally travel to Cuba in 5 easy steps, after Trump’s changes

I. Legal Resources for Cuba Travel

The first and most important thing you should do is to familiarize yourself directly with the language in the regulations. The most important information resource straight from the U.S. Treasury page are:

Download these PDFs onto your phone. They can be useful if you’re pulled over by immigration like I was.

II. Quick Summary of the Restrictions for Legal Cuba Travel from the very beginning:

Contrary to popular misconception for the past 5+ decades, and still as of today, February 2018, going to Cuba for “tourism” is still ILLEGAL because the U.S. embargo against Cuba is still in place.  Not even under President Obama was tourism legal, not the embargo ever lifted. Only Congress can lift the embargo. This means you still can’t go to Cuba to relax, for pleasure, or for recreational activities (tourism). BUT! The Obama administration relieved the stringency of these regulations. As of 2018, you can still go IF you have a purpose.

Related: Ten Reasons to End the U.S. Embargo 

  • You still must have a purpose, other than tourism, to go. There are twelve self-licensed categories for you to choose from (see section III below).
  • The best part of the recent regulatory changes is that now you can self-license yourself. If you believe you qualify for a category, you go under it by self-proclaiming it to yourself. That simple. You no longer need to submit application paperwork to OFAC for a license (awesome!).
  • You should read thoroughly through the full definitions of the twelve categories in the laws and FAQ (section I provided above) to figure out which category applies the best to you.
  • Whatever purpose you choose to go under, cannot support tourism.
  • This means you cannot go under “journalism” and write an article promoting tourism. But you could write about Cuban coffee, the culture, politics, etc.
  • It is believed that these amendments are intentionally vague to allow more leeway for people to figure out a way to go
  • If you wish to engage in any travel that does not meet the requirements of a general self-license, that’s when you would need to apply for a specific license from OFAC (paperwork and application).
  • But remember! The U.S. has the right to audit you within 5 years of your trip, so keep all your receipts and an itinerary.

III. These are the twelve (12) categories:

  1. Educational activities including People-to-People  [Pick this one only if you booked part of your trip before November 8, 2018/Trump changes. It’s the easiest one – See next section below]
  2. Professional research and professional meetings
  3. Public performances, clinics, workshops, athletic and other competitions, and exhibitions
  4. Religious activities
  5. Humanitarian projects
  6. Journalistic activities
  7. Family visits to close relatives
  8. Support for the Cuban people (includes non-formal educational training) [Pick this one if you booked your trip before November 8, 2018/ Trump changes]
  9. Exportation and re-exportation of certain Internet-based services
  10. Certain authorized export transactions including agricultural and medical products, and tools, equipment, and construction supplies for private use
  11. Activities of private foundations or research or educational institutes
  12. Official business of the U.S. government, foreign governments, and certain intergovernmental organizations

Again: if your travel falls within one of these categories you are authorized to self-license yourself to visit Cuba legally without having to submit any application paperwork to OFAC.

As Robert Muse, a Washington-based lawyer who specializes in U.S.-Cuba related law told the New York Times:

“If somebody wishes to travel to Cuba and they can’t think up a way to fit into those categories, they are not trying.”

Just remember! You must have a jam-packed itinerary before you leave. Quoted directly from the CACR, your itinerary must not…

“include free time or recreation in excess of that consistent with a full-time schedule”

IV. Choosing the Educational Category (People-to-People) to Travel to Cuba

If you booked some or all of your trip BEFORE November 8, 2018, the easiest way to still go is through your own educational (“People-to-People”) tour created by you. I met people on these licensed tours who were on guided hike tours to waterfalls and beaches. These are arguably all tourist activities, but because they were with a Cuban the entire time and/or simultaneously involved in educational activities about Cuba and Cubans, they were still technically engaged in an educational cultural exchange that satisfied educational category license (#1).

But this doesn’t mean you can go to Cuba, talk to a Cuban and then head to the beach. Here is one example that does not qualify according to the CACR:

“An individual plans to travel to Cuba to participate in discussions with Cuban farmers and produce sellers about cooperative farming and agricultural practices and have extended dialogue with religious leaders about the influence of African traditions and religion on society and culture. The individual also plans to spend a few days engaging in brief exchanges with Cuban food vendors while spending time at the beach. Only some of these activities are educational exchange activities that will result in meaningful interaction between the traveler and individuals in Cuba, and the traveler therefore does not have a full-time schedule of such activities on each day of the trip. The trip does not qualify for the general license.”

Directly from the Federal Register/CACR/Treasury website:

“Travelers utilizing this general license must ensure they maintain a full-time schedule of educational exchange activities intended to enhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people’s independence from Cuban authorities, and that will result in meaningful interaction between the traveler and individuals in Cuba. The predominant portion of the activities must not be with a prohibited official of the Government of Cuba, or a prohibited member of the Cuban Communist Party.”

The moral of the above stories (taken directly word-for-word from the U.S. regulations) is that your itinerary must consist of a FULL schedule of educational activities to satisfy this category license.

RelatedMy seven-day solo trip through Cuba

However, assuming you’re not strolling back into the country with a beach hat, visible bikini straps, and sand in your shoes, holding photos of you tanning on the beach, it is hard for a U.S. regulator to prove that you did or did not fully comply. They weren’t in Cuba with you watching your every move.

But regardless, have a packed itinerary ready to show immigration (just in case).

V. Creating a Legal Itinerary

You can make your own tailored to the purpose. If you need assistance, I sell comprehensive templates or custom-tailored legal itineraries for your trip. Click here for prices and info.

VI. Flying to and from Cuba/United States

There are several legal ways to get there.

USA Commercial FlightsSince June 2016 , you can book your own flights online to a ton of Cuban cities on American Airlines, JetBlue, Silver Airways, and more… Legally and directly from the USA! No need to go through Canada or Mexico anymore. And the prices are VERY good.

Third Country: Depending on your preferences/departure city, it could be easier to take a flight to Mexico or Canada and then transfer to another flight to Cuba. This is also legal, but not necessary.

  • Websites/companies I recommend to search for your flights out of a third country (there are many more):

Chartered Direct from various US cities: These guys are quickly going out of business since commercial flights became legal again. But just in case… this is another (very old school) way of flying from various U.S. cities to Cuba. I don’t recommend them since they’re pricier, but just in case:

VII. Cuba Visas/Travel Cards

The airline that is taking you to Cuba, will be the one to sell you a travel visa. This is very easy. This does NOT have to do with your category. Categories/purposes are for and required by American authorities. A travel visa is for the Cuban authorities. Just like the US requires foreigners to have a travel visa, too. The irony about this all is that Cuba will label your visa as travel tourism (see above), regardless of what you’re telling the U.S. Remember they are two different countries with different laws. Cuba does not support or uphold the embargo, the U.S. does. So to the U.S. the label will be one of the categories/purposes listed above. To Cuba it’s going to be this visa above.

  • Cubana Airlines – $20 (via Canada)
  • Interjet – $25 (via Mexico)
  • JetBlue – $50 (USA)
  • Delta – $50 (USA)
  • American Airlines  – $85-100! (USA)

Some airlines will ask you to sign an affidavit promising that you are going for a purpose other than tourism (relaxation/fun). Then you’re off! That’s it. No application. More info on handing in the Cuban visa below.

VIII. My Personal Experiences Leaving to Cuba

(a) From Cancun, Oct 2015

Mexico did not care that I was going to Cuba. They did not ask me any questions or make me fill out any paperwork pertaining to Cuba.

 (b)  From Toronto, Dec 2015

Just like Mexico, Canada did not care that I was going to Cuba.

 (c)  From NYC, Oct 2016

I got my visa for $85 ahead of time through Cuba Travel Services and flew American Airlines to Miami. At the Miami counter, there was a travel company by my gate that looked at all of my documents to make sure I had the travel card/visa. They stamped my boarding pass and that it was it. No questions asked.

(d)  From NYC, Feb 2017

I paid $50 for my visa at the JetBlue counter. They have a special Cuba section at the JFK airport. Then I was off. It was so casual that they forgot to ask me to sign an affidavit. I saw the pile of affidavit forms on the counter, but I didn’t bother reminding them.

VII. Getting Through Cuban Immigration

Do not lose your Cuban tourist/travel visa card. You will hand over one-half of it upon arrival to Cuban immigration, and the other half when you exit Cuba. Like I said above, be sure to be mindful of Cuban laws too, not just U.S. laws.

For example:

  • Cuba requires specific visas for journalism, studying, and doing business in Cuba
  • Bringing items to either sell or give away in Cuba can be subject to customs regulations and/or taxes. But you can always bring items for your own personal use and decide later during your trip that you don’t want them anymore… 😉
    • Careful with laptops if you bring more than one per traveler, they might think you’re trying to sell it in Cuba.

I asked the immigration officers not to stamp my passport (for peace of mind), every time they kindly obliged.

October 2015 & December 2015

I wasn’t asked why I was visiting, where I was staying, who I was seeing, or what I was doing. Nothing. I can’t recall any real questions both times I went. I wasn’t asked for medical insurance to enter Cuba. It’s now covered by the American airline if you’re flying from the US. I wasn’t given any security interrogation (unlike two other solo tourists I met). The only question I was asked was if I could stop smiling as they tried to take my picture.

October 2016

When I got to the Camaguey airport, I was taken aside from the immigration booth for questioning. They asked me:

  • What was my age? (four times)
  • Why was I in Cuba?
  • Who was I traveling with?
  • Was with a tour group or alone?
  • Was I doing people-to-people?
  • Had I been to Cuba before?
  • Some other random questions I can’t remember

I was nervous, but I answered confidently until diffusing situation the Latino-Caribbean way: with humor. By the end of the conversation, we were all laughing and I was back to the immigration queue. I got stamped and went off.

February 2017

The same process from October and December 2015.

VII. Immigration: Getting back into the U.S.

This is the scariest part because it’s not Cuba who has a problem with people traveling there. It’s the U.S. and its still standing embargo against Cuba. Arriving in Mexico or Canada from Cuba was completely normal without any problems at all, these countries don’t really care. It’s not their anti-Cuban government laws or embargo.

(a) Havana to Cancun to Newark, Oct 2015

Because I have Global Entry ($100, waived if you have certain credit cards), at Newark Airport, I didn’t even have to speak to an immigration officer. I went to a Global Entry kiosk/computer that asked me, “Did you just come from Cancun? Do you have any of the following [ridiculous] items?” I answered honestly — Yes I just got back from Cancun. No, I’m not bringing back cows or explosives. I handed the receipt to an officer and just like that, without a word, I was strolling back into the country as if crossing a state border.

As far as the U.S. government knows, I didn’t even go to Cuba that time.

(b) Havana to Montreal to Newark, Jan 2016

My flight from Cuba to Montreal was delayed. So, I missed my Air Canada flight back to Newark from Montreal because my Air China flight out of Havana was delayed by several hours. Neither Air Canada (the flight I missed), United (the platform I used to purchase the ticket) nor Air China (the delayed connector) wanted to give me a new free flight. They said they had no obligation to do so, because I booked the trips separately. Thankfully, after lots of begging, United spared me a free flight to Newark …for the next day.

(c) Trouble at the U.S. Immigration Booth in Montreal

** This is important ** Montreal (YUL) and Toronto (YYZ) have international agreements with the U.S. These airports have U.S. immigration booths. That means you pass U.S. immigration in Canada, not the U.S.

My experience here was completely different here. In Canada’s U.S. immigration booth, I still had to speak to an immigration officer even though I went through a Global Access kiosk.

The immigration officer asked me why I’d been in Montreal for only a day and I honestly said: “Because I went to Cuba.” She responded, “Were you authorized for that travel?” and I affirmed. She asked if I brought anything back from Cuba, and again I answered honestly, “Yes, rum and chocolate.” She pursed her lips and let out a sigh. She hit the red “X” on her computer screen and told me to follow her. I sat in the immigration office waiting to be called. She whispered to an immigration officer, who looked underwhelmed by her concerns. He shrugged and whispered, “There are a lot of them coming and going to Cuba now..” before turning his back to me to continue whispering.

Finally, when I was called up, a young officer asked me why I went to Cuba. He seemed to not be fully aware of the regulatory changes, so I explained which license I went under. The officer then asked if I had applied for the license, to which I explained I didn’t have to as per the recent amendments, which I pulled up on my phone to show him along with my itinerary. He asked where I got the PDFs from, and I explained they are the OFAC amendments to the CACR on the U.S. Treasury website.

He then asked what I thought of Cuba. I answered with the most pro-capitalism, pro-America response I could muster up.He seemed satisfied and agreed that the new regulations are pretty vague. Before welcoming me back into the country, he kindly informed me that to bring back Cuban rum I have to bring it directly to the U.S. with no international layovers. But he seemed to not want any issues and said he’d make an exception and allow me to bring back the rum. Ecstatically, I thanked him and raced to my plane back to New York City.

Before officially welcoming me back into the country, he kindly informed me that to bring back Cuban rum I have to bring it directly to the U.S. with no international layovers. But he seemed to not want any issues and said he’d make an exception and allow me to bring back the rum. Ecstatically, I thanked him and raced to my plane back to New York City.

(d) Flying into Miami, U.S.A from Varadero, Cuba

I landed in Miami. Swiped my global access card and went to the counter to hand over my receipt. I noticed then and there: everyone at the airport was Cuban. The customs officers, the immigration officers, border patrol, the janitors, the security guards. The immigration officer said “where’d you just come from?” and I said “Cuba.” He began to ask “Wh—” but I cut him off in wonder “But I gotta say, it feels like I’m still in Cuba!” I pointed and began speaking in Spanish, “Everyone here is Cuba. You are Cuban, he is Cuban, everyone is Cuban“. I explained I was a Dominican New Yorker, we exchanged jokes and laughter, and I strolled back into the country with zero questioning.

“Los Dominicanos y los Cubanos comparten los mismo chistes” – Cuban man in Camaguey

My friends without global access said they had zero questioning in Miami and were simply told: “Welcome back home”.

(e) Flying into NYC, U.S.A from Havana, Cuba

I signed into the Global Access computer. I handed the immigration officer my receipt. He nodded. I kept it moving.


*Please note, you do not have to be a U.S. citizen to be subject to U.S. jurisdiction. Click the link to see if you qualify.

**This is not legal advice. Please keep in mind that these laws are continuously changing. I try my best to update them as soon as I hear anything. Click here for my recap of Trump’s announcements and here for the five easy steps to travel to Cuba legally, after Trump.


Got any questions? Anything I missed? Confusion? Post a comment question below! 🙂

30 thoughts on “Legal Travel to Cuba from the U.S., 2018

  1. Pingback: Practical Tips for Traveling to Cuba – International Insights and Travel

  2. Kevin says:

    Thank you so much for all of this info! My question is: what info do I need to provide to prove that I’ve done what’s on my itinerary if they ask?

  3. Pingback: Practical Tips for Traveling to Cuba - DESTINATIONS | TRAVEL HACKS | POLITICS |

  4. Shevy says:

    This was so informative. I was planning on going through cancun just like you. Do I still need to pick a category and have an itinerary if I am going through another country and purchasing a tourist card?

    • G. Isabelle says:

      To go legally, yes. And it’s very easy to do the educational one. To go illegally, no you don’t need an category/itinerary. Tourist card/visa that Cuba gives you is separate from the 12 categories that the us mandates. I know it can sound confusing, I think both countries define tourista differently is why. 🙂

  5. Amy says:

    Thanks so much for this! I cant wait to hear you report back on your direct flight experience in October since I am planning on doing that myself soon! Thanks again and safe travels!

  6. Ignacio says:

    Hi, thanks for the post! i am from Argentina but i´ll be visiting Cuba from US, so i was a bit scared on all this matter of the 12 categories. May i ask if you can send me the example of your itinerary? i´d also like to ask if when you are leaving US, customs ask you something more than the itinerary?

    Thanks. Regards

    • Isabelle says:

      My itinerary was special to my personal circumstances. But you can find OFAC approved itineraries on the links above. And the easiest, most fool-proof, legal way to go is Educational category, under individual people-to-people group tour. I offer hourly consultation services for Cuba travel, if you would like for me to help you set up an itinerary and pack together all the necessary documentation for you in case you are questioned by Cuba or the US if you want to me 300% safe? But most likely, no one will ask for these things and you will have a seamless trip 🙂

  7. Kenza Aloui says:

    Dear G. Isabelle,

    I’m glad that I found your blog, after so much research !
    I’m a free-lance journalist, foreign, flying from the US to Cuba, on a direct flight from an American company. I emailed OFAC to know if they had a list of justifying documents to show at the border (to proove my journalist status) they say they did not.
    So I’m planning to fly with a schedule, a pitch for the paper I will write, maybe a letter from my editor and print some pieces I wrote in the past.

    Were they annoying to you at the border (the Americans) ? What about the Cubans ?
    I’m planning a Paris-New-York-Havana-NewYork-back to Paris, France.

    Thank you so much

    • Isabelle says:


      At the US border in Canada–yes, they asked me questions. I showed them the US gov’t PDF links above on my phone (saved as iBooks) and explained why it was legal for me to go. They asked what I was doing, why I was there, if I went with a group, what I thought about Cuba, etc. A lot of the immigration officers aren’t fully aware of the regulatory changes themselves. Bringing the itinerary doesn’t hurt (I was 200% prepared), and it’s better to be safe than sorry. But it’s likely that your trip will all be totally seamless.

      The Cubans on my third trip did question me a lot. I’m not sure why. I got out of the questioning sooner than later via honest answers and finally the latino way… humor and jokes. I have a few theories for why they pulled me aside and questioned me, but I’ll never be 100%.

      Enjoy Cuba! It’s a special place 🙂

  8. James says:

    I am planning to travel there this week from Canada, I was wondering how did the officer know you were in Montreal just for 1 day if you flow to and from Cuba from Montreal? Was your passport stamped?

    • Isabelle says:

      Hey James, the officer asked me “how long you been in Montreal for?” And I said “one day”. I don’t know if she would have known otherwise. My passport wasn’t stamped the first time. Then I got lazy and stopped asking for it to not be stamped. I’ve heard that recently some people ask to not get it stamped and they now don’t oblige w the progression in US-Cuba policy…

      • James says:

        Thanks for the answer. I have a Global Access as well, just wondering when you went through Montreal did you check that you been to other places other than Canada?

        • Isabelle says:

          Global access is nearly useless in Montreal because you still have to make a line and see the immigration officer behind the booth. The machine at global access just asked “did you just arrive from Cancun?” No mention of Cuba. I don’t remember what the Montreal asked me, but I know it had no mention of Cuba either.

  9. Laura S says:

    Hi Isabelle! Thanks for all the useful information.
    Me and my husband are planning to flight into Havana through Mexico City. We are US residents and feel like traveling directly from NYC would be risky (even under the 12 categories). Do you have any advice you would recommend? Is better to booked different airlines? Does your passport get stamped twice when flighting from the US and then coming back from Havana? How risky would it be to have those 2 stamps of entry in your passport??

    Thanks in advance!!

    • Isabelle says:

      Hi Laura, if you want to be super safe you can bring a legal itinerary under the requirements of OFAC. How many days are you going for? I make itineraries for people if you’re interested want to be extra super safe.

      Personally, I recommend using one airline and flying directly from NYC to avoid potentially missing a flight like I did in Montreal.

      And yes, my passport did get stamped twice. Not risky at all. Are you both American nationals?

      Either way… Go for it! Experiencing Cuba can be life changing 🙂

  10. Emelyn says:

    Hi Isabelle,

    Thank you so much for the detailed info. It was great help! I read that U.S citizens and residents both fall under the jurisdiction. I just wanted to confirm because my dad is going in August and he has a green card (US resident) and Dominican passport. He will be fine going in and out of the IS right? I bought direct flights through Jet Blue.

    Thank you!

  11. Pingback: Travel to Cuba After Trump: What The Legal Changes Mean & My Thoughts - Dominican Abroad

  12. Nat says:

    Hi! To begin with, thank you for all the work you’ve done and keep doing! I am not a U.S. citizen, but I am currently in the U.S. and have a question regarding my trip to Cuba this coming spring. I would be delighted if you could answer my question privately, especially since you say you can assist with itineraries. Is there any other way I can contact you?

  13. LIsbet H. says:

    Hi Isabelle,
    Im planning a trip to Cuba this spring,I would be flying out from NYC. I am not an U.S citizen but I have a green card (US resident) and Dominican passport. My question is: do I need any additional visas or documents and will I be fine going in and out of the country?

    • Isabelle says:

      Hi Lisbet, you will get your visa with the airline. No one will likely ask for this but you are legally suppose to have an itinerary and records/receipts for up to 5 years in case of an audit.

  14. Dorie says:

    Hello. We would like to fly from Dominican Republic to Cuba for a couple days. We are Americans and we’re going from the US to DR for vacation and want to go to Cuba from DR and then from Cuba back to the US. How can we make this happen? This Trump law has me so confused. We work in Kuwait and when we vacation we like to go to many different places. Thank you for your help in advance.

  15. Diana says:

    Hey Isabelle! When you say “booked your travel” before Nov 8, 2018, do you mean you made a transaction (ie, booked a flight) before that date or do you mean you are travelling before that date? I am looking to book a trip next Jan/Feb. If I need to buy a flight really quickly I will.

    Thanks for your informative article!

  16. Coleah Mattern says:

    Hi! So much great info here- thank you! I am wondering about the stipulation on the “people to people” option that we should have booked part of our trip prior to November 8th, 2018. I can’t find anywhere else that lists that particular date as important. What am I missing? Making sure I don’t need to go buy a flight today!


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