Visiting Cuba: tickets, medical insurance, and visas.


As an American, Cuba has always been a fascinating place, a forbidden land of mystery. When the travel ban was lifted, our curiosity got the best of us, so we decided on Cuba for our first international trip as a family.

Prior to our trip, I googled information, read several blogs on tourism in Cuba, and bothered every person who wrote #Cuba on Instagram. I soon found that the information I gathered wasn’t consistent. Confusion loomed over where to purchase a tourist card, what to see, and how much money to bring. My anxiety heightened by the lack of information.

Despite the headaches and the eye twitching that came immediately while checking in our bags, our misadventures became a learning experience and for that, we are grateful. Let me set the record straight so you can leave your headaches in the US and enjoy your Cuban vacation!

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Riley and I strolling through Havana


Booking your flight:

There are 8 major airlines that fly to Havana. We booked our ticket with Frontier since it was about $200 cheaper overall including baggage fees. When we booked our flight, we were asked on the Frontier website what our reason was for visiting Cuba. Americans are banned from visiting for tourism so you must choose a reason that makes the most sense. We chose “Support for the Cuban People” because we were spending our money and helping out the economy. For other airlines, such as Southwest, you are asked your reason at the counter prior to obtaining a visa. Please remember, US visitors are required to keep an itinerary of their activities and it must match your reason for visiting. Apparently, our government can ask for our itinerary years after a visit. So keep track of what you’re doing and make sure it consists of more than just hanging out at the beach and drinking rum.

Medical Insurance:

American citizens are required to have Cuban medical insurance prior to entering Cuba. Check with your airline to see if it is covered with the price of your fare. Since we flew with Frontier, our medical insurance was paid through our tickets, so we didn’t have to worry about purchasing it elsewhere.

Cuban Tourist Visa:

The information on obtaining a visa was the most confusing ordeal of my life. The Frontier website had no information other than a link to a company that sells the visa and sends it to you for $110. I was informed by friends who had visited that visas could be purchased at your connecting airport for $50. After speaking with several people, we decided not to purchase the visa ahead of time and waited until we got to Miami.

Here’s the kicker and the beginning of my headaches/eye twitching; when we checked in our bags at DIA, the woman at the Frontier counter asked if we had our visas. When I told her we would purchase it in Miami, she said there was no guarantee they would have visas for us in Miami then said ” well, your bags will be in Cuba, but you might not be. Good luck.” Can you believe that?! She also mentioned how we risked being detained with a $3000 fine for not buying it ahead of time. Thanks to her, I didn’t sleep on the plane and I was sick to my stomach the entire flight to Miami.

But of course, I shouldn’t have worried and should have trusted what I knew. Once we got off the plane, we heard an announcement asking passengers to Havana to come to the Frontier desk. They had visas! Stacks and stacks of visas. And I cursed the Frontier lady at DIA for worrying me for no reason. So here’s my advice: flying with Southwest? Wait it out and buy your visa at the counter because it’s only $50. For the rest of us, it’s $100 per visa although I don’t understand why there is a price difference. I thought I was going to save money by buying it in person, so if I were to go back, I’d buy it online. And please remember, do not make mistakes on the visa. One mistake will force you to fork over another $100 for a new one.

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For my next post, I’ll outline all the things you need to bring like loads of cash and sunscreen. Did you know Americans can’t use credit cards and debit cards in Cuba? Yes, cash is king. And did you know there is literally no place to buy sunscreen? I’ll outline all of it in my next post on what to bring and how to prepare. Stay tuned and leave any questions below!

27 comments on “Visiting Cuba: tickets, medical insurance, and visas.”

  1. I’ve always wanted to visit Cuba, it does sound like a fascinating place. Fortunately I’m a South Africa and a Cuba visa is one of the easier ones for us to apply for. Glad everything worked out okay for you gyts.


    1. You are so lucky!! We were really jealous of everyone who wasn’t American. A Cuban vacation is so much easier. But overall, I’m glad we went. It was quite the experience. Thanks so much!!

      Liked by 1 person

  2. It is very interesting reading the requirements for travel to Cuba. I love the colors, vintage cars and the architecture. Would love to go someday and this post is super helpful. Thanks for sharing and clarifying!

    Gennifer Rose |


    1. We really loved our time there and I’m so glad we went! But it is definitely a different experience as an American. I think you would enjoy visiting. Thanks for reading! 🙂


  3. Thanks for the info. I didn’t know purchasing a visa ahead of time can be such a rip off (for this situation anyways). I’ve never had to purchase a visa ahead of time for any country I’ve been to, I’ve always just get it while I’m there. But then again, I’m just vacationing, maybe there’s other reasons for needing it ahead of time.


    1. This was definitely new for us too! Usually, Americans can just go wherever, so this was a bit overwhelming especially with all the conflicting information prior to our trip. Thanks for reading! Happy travels 🙂


    1. It’s incredibly complex. And even more confusing that the information is not consistent. As soon as I got back, I knew I needed to write this post! Thanks for reading 🙂


  4. This is such an useful information! My parents are both retired and they are dreaming with a trip to Cuba, I don’t thnk they need a visa though, as they are both Argentine.


    1. It was pretty amazing. Walking through old Havana was so interesting. I actually felt like I was in Europe at certain places! I’m happy to hear you found this helpful 🙂 Thanks for reading!


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