As of June 2019, US Citizens cannot get deposited onto the island of Cuba by a cruise ship, and they cannot tick the people-to-people box that was popularized in March 2016 during the Obama administration.
Short of entering illegally via non-stop flights from Cancun, Panama City, or Port of Spain, what is a US Citizen to do?

How do you visit Cuba legally?
As per the US Embassy in Cuba, here are the 12 categories of authorized travel:
- Family visits
- Official business of the US government
- Journalistic activity
- Professional research and professional meetings
- Educational activities
- Religious activities
- Public performances, clinics, workshops, athletic and other competitions, and exhibitions
- Support for the Cuban people
- Humanitarian projects
- Activities of private foundations or research or educational institutes
- Exportation, importation, or transmission of informational materials
- Certain authorized export transactions
Keep in mind: you will not need to apply for an OFAC (Office of Foreign Assets Control) license if you meet the criteria for one of the 12 categories. You will, by default, be traveling under a General License because you meet one of the 12 categories. (Do not confuse this with a Specific License, which requires special permission because you are traveling as a US Citizen to Cuba without meeting the criteria for one of the 12 categories.)
How flexible are the categories?
Before you apply your own definitions to the 12 categories, make sure to read the extensive FAQs on the Cuba Sanctions page of the US Department of the Treasury website, for each of the 12 categories is defined.
Once you find a category that may work, keep in mind that you must spend 6-8 hours per day meeting the criteria of that category.
Which category is easiest?
Assuming you do not have family in Cuba, and assuming you are not a full-time journalist, the simplest way to travel under a General License to Cuba is to meet the requirements for one of these three categories:
- Professional research and professional meetings
- Athletic competitions
- Support for the Cuban people
Depending on your profession, there may be conferences in Havana that you can attend (this might tick the “Professional research and professional meetings” category).
If you are keen to bike a century, run a marathon, or enter a golf tournament, you might be able to justify 6-8 hours toward ‘Athletic competitions.’
During my trip to Havana, I only met two US Citizens, both of whom were traveling together under the “Support for the Cuban people” category. When asked how, specifically, they were justifying their 6-8 hours per day of support, they explained how they brought two large suitcases filled with toilet paper, rain ponchos, and bicycle-tire-repair kits. They found tours on GetYourGuide and Airbnb Experiences, which enabled them to meet Cuban people and to offer their support.
How do you get to Cuba?
Once you can confidently prove (in detail) that you are meeting your chosen category’s criteria for each day in Cuba, you should be able to book a flight via United, American, Delta, jetBlue, or Southwest.
Do you need a Cuban Visa?
You will need a Cuban Tourist Card. If you want to purchase yours ahead of time, you can pay $85 through Cuba Visa Services (that’s what I did). However, Cuban Tourist Cards should also be available for purchase at the “gateway departure gate” (that is the departure gate for the flight that goes directly to Havana. In other words, I flew United Airlines from Los Angeles to Houston, and Houston to Havana. In Houston, which was my gateway to Havana, I could have purchased a Cuban Tourist Card for $50 at the departure gate).
Where should you stay in Cuba?
Hotels are fairly easy to book. I simply booked via Hotels.com. (Keep in mind: the US government forbids its citizens from staying at certain hotels. For a list, check out the US Department of State’s List of Restricted Entities.)
What about currency in Cuba?
Money is a bit frustrating in Cuba. US credit cards and ATM cards are not accepted, so you must bring cash. When you arrive at Havana Airport (Jose Marti Int’l Airport, La Habana), you’ll likely see a serpentine line of people (mainly Europeans, Chinese, Japanese, Mexicans, and Canadians) exchanging their currency (euros, wan, yen, pesos, and loonies) for the “cuc” (Cuban Convertible Peso).
If you set up airport transportation prior to your arrival (I did so via my hotel), then you can bypass the currency exchange line and just exchange currency in small bursts at your hotel.
Be warned, though. There are two currencies in Cuba: the “cuc” and the “cup.” The “cuc” is for foreigners and is worth approximately 25 times more than the “cup,” yet the bills look awfully similar. Be vigilant.
Also, if you’re exchanging US dollars, you might avoid $5 bills, as the people I met were not eager to have that denomination.
Do you need a power adapter in Cuba?
Many of the hotels are wired for 220v, so a standard plug adapter won’t be sufficient. Bring a power converter (I brought a Bestek Power Converter to convert 220v to 110v).
Do you need health insurance?
Bring proof of health insurance. (I wasn’t asked to provide proof when I arrived at the airport in Havana, but I expected that airport personnel would not only ask but also require that I purchase health insurance for my stay.) The US Embassy in Cuba offers more insight here.
Once you enter Cuba, what should you do? What will you see?







Is a trip to Cuba worth it?
It’s difficult to speak for other travelers and, specifically, residents of other nations. While in Cuba, I saw travelers from Poland, China, Japan, Mexico, and Canada. I only met two US citizens, and that’s the attraction. Cuba is currently much more forbidden (for US citizens) than it was seven months ago. For me, that makes it more interesting.
As always, if you have any questions, please comment below, or feel free to contact me.
Haven’t seen any posts for a year. Really enjoyed your work and following your travels. Hope everything is ok.
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Thanks Brian! I hope the same for you and your friends and family. I appreciate your kind words. I’ll get back to posting once international travel for Americans can be done with less risk to the other passengers (on the plane) and less risk to the residents of the country that we’re traveling to.
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