3 Tips for Traveling to Cuba

How to get there and back without getting fined.


You Still Need a Reason (and some documents)

Traveling to Cuba is not simply a matter of business or pleasure. Although you don’t need expressed permission from the Treasury’s Office of Foreign Assets Control, you do need to have a reason for travelling to Cuba that falls under one of 12 categories permitted by a “general license.” The full list is available here on the Treasury’s website, but you should be aware that one the categories is not “Vacation.”

3 Tips for Traveling to Cuba

Street art in Havana

It’s rare that an American is reprimanded for a trip to Cuba. That said, if the Department of Treasury were to find out that you traveled to Cuba, they are going to want proof that your trip was for an explicit reason. Entry to Cuba is permitted for family visitation, religious ceremony, journalism, humanitarian missions, and even for attending a sporting event. More generally, you can travel there for person-to-person contact and educational or humanitarian reasons (but not for your bachelorette).

3 Tips for Traveling to Cuba

Feeding a street dog (a nursing mother) in Havana. I tried to bring dog food wherever I went.

If you’re interested in volunteering, there are many organizations you can team up with. Check out this program to help the cats and dogs of Havana, and check this listing to see if any other humanitarian missions interest you. This way you’ll not only get to experience a broadening of your mind — but also of your heart.

3 Tips for Traveling to Cuba

Crossing the street, with my dad (in the fedora)

Make sure to check this gov website for current details. All travelers to Cuba, including religious workers, should contact the Cuban Embassy (tel: 202-797-8518) in Washington to determine the appropriate type of travel card/visa required for their purpose of travel. Cuba requires visitors to have non-U.S. medical insurance, and sells a temporary policy to those who do not have it. Questions about this insurance requirement should, again, be directed to the Cuban Embassy. Alternatively, you can travel with one of many “Cuba USA” tour operators, and they will arrange all the necessary documents for you. As always, make sure to check reviews (even the “filtered” ones on Yelp, which are usually valid reviews). Here’s a great FAQ article via CNN, and another via the NY Times, that will answer more of your questions.

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A writer, artist, and designer since she was young enough to put pencil to paper, Hilary taught herself code and created Urbanette when she was a teenager. Currently, she lives in Monte Carlo, but spent the past decade living in NYC, still considers herself a New Yorker, and visits regularly. She's always traveling, looking for hot new topics, destinations, and life hacks to bring to Urbanette readers.

Reader Discussion: 110 Comments

  1. Will definitely visit Cuba sometime this year. Simply because of the old cars. I’m a huge car junky and really love the classics. Such elegance and slick designs. It’s like a shiny bucket of death. We all know the safety standards of old cars right?

  2. Lynn Hayes

    Cuba is definitely on my list of places to get to soon and this is such a thorough guide! Lots of things I didn’t know. Thanks for putting it together! I actually had a Cuban sandwich for lunch today in Cambodia of all palces, and it wasn’t that great 😉 lol

  3. Roberta Bennett

    This is a really extensive guide! Fantastic post with great info! Planning our visit at the moment. Cheers!

  4. Frances Seifert

    This article is so helpful! We are currently trying to figure out how we will plan our trip. We looked into th people-to-people tours, but they seem to be a bit too organized for our taste. The trampoline method could be the best option, but my husband is a bit nervous that something could happen, and we might have trouble getting out of the country if so. Thanks for putting this together… I am going to be bookmarking it to help with our plans!

  5. Amanda Roberts

    What a comprehensive guide to travelling to Cuba. It’s helpful to see the tricks and catches pointed out to help with the planning. Simple things like slowing down and taking extra care with the forms to avoid duplicated costs and non-US based travel insurance are easy things to miss.

  6. Kimberly Thompson

    I just returned from Cuba a few weeks ago, it was so amazing! Def stay with a local family in a casa cheaper and great experience.

  7. Emma Blackwood

    Cuba is such an enticing and exciting destination right now. I wanna get the opportunity to experience it before massive tourism takes over.

  8. Catherine White

    Great tips! I hadn’t realized that Cuba would be such a gorgeous country. I would really love to visit Cuba someday. Their history and culture sound quite interesting.. Great tips for those who would like to travel there for the first time.

  9. Nicky Bryan

    Thank you for these tips! Thanks Hilary. I have friends that recently went to Cuba and they spent a fortune. I want to make it on a budget, at least I’ll try!

  10. Pearl Nguyen

    Thanks for the tips! I did not know it was so expensive to go there. Hopefully, I get to go one day.

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