Traveling to Trump’s Cuba: What You Need to Know

While you can usually purchase last minute airfare, grab a bag and head to your favorite vacation destination with ease, some locales call for a little more preparation to get there legally and hassle-free. Cuba required LOTS of prep and planning ahead of time. We had been wanting to go since Obama lifted the embargo and Grant’s surprise 30th birthday trip seemed like the ideal time to visit!

See our Cuba recommendations and travel guide here.

art in havana

Traveling to Cuba- What you need to know:


As an American citizen you will need a visa to visit Cuba. There are 12 reasons Americans can qualify for a visa according to the US Embassy website. These reasons vary from journalistic activity and family visits to humanitarian work and educational activities. A sub-category of the educational activities is people-to-people travel which promotes Americans interacting with and learning from the Cuban people. I did my due diligence and prepared us to qualify for the visa.

Planes were booked, visas were purchased, reservations were made… and then came June 16th #thanksTrump. We were scheduled to leave in 2 weeks when our Commander in Chief decided to switch up the Cuba rules once again and announce that he is tightening restrictions so Americans can not plan their own travel to Cuba and that new rules would be strictly enforced for Americans visiting for tourism under the people-to-people visa (the visa we were using and the only one we qualified for) Um..yikes!

We went for it anyways and here’s the lowdown.

What we did to prepare:

  • We stayed at an Airbnb (Casa Particular) so we were guaranteed to interact with the Cuban people. It was such a fabulous airbnb!
  • I booked a tour to Vinales with Havana Journeys and they provided us with a 1 day full itinerary showing we qualified for educational tourism (simply ask and they will send it to you).
  • I printed out the itinerary from Havana Journeys and created a personal itinerary for our group.
  • We called our airline ahead of time to purchase our $50 tourist card (why they call it a tourist card when tourism isn’t allowed, no idea!) You can also do this at the airport but be sure to get to your gate more than an hour in advance.

What happened in reality:

  • Customs was a breeze re-entering the United States. We have Global Entry so it was extra fast and the customs officer only asked where we came from and if we had any alcohol or tobacco products. Obviously we had cigars and he asked how many we had with us. We had 20 which was fine, I’m not sure the exact number allowed but it is a lot! THAT WAS IT!! No getting the third degree about why we were in Havana, no asking to see our visas, no secondary questioning room and incessant interrogation on how we interacted with the Cuban people…it was simple as that. 20 minutes later we were sitting in the living room eating pizza.

Side Note: Our friend who went with us has a Cuban cousin who lives in Havana so he and his wife traveled under the family visit visa and we visited his cousin one afternoon. He has Global Entry and she does not but they both had a hassle-free time in customs as well.

What’s next?

Apparently President Trump’s changes are going into affect quickly. The gate agent at the airport in Atlanta said after September 2017 it will be much more difficult to travel with the people to people visa, and the host at our airbnb in Cuba said he has had several cancellations that were scheduled for the fall. I can only speak from our experience but it didn’t seem like too much was being enforced during our visit during July 2017. I imagine people who still want to travel to Cuba and don’t think they will qualify for one of the other visa purposes will resort to the age-old sketchy method of connecting through Canada or Mexico.


US credit and debit cards do not work in Cuba…at all! Don’t even think about packing your Benjamins either, you will get a horrible exchange rate. You have to first switch to Mexican Pesos or Euros and then exchange those in Cuba for the local currency, CUC or CUP. (Oh ya, there’s 2 local currencies, could it get any more confusing!?) CUC is about 1 to 1 with the USD and is what we used most of the time. CUP is used for less touristy transactions or for cheaper purchases and is about 40 to 1.

We exchanged some money at the airport when we first landed in Havana and more at the bank later in the trip. The rates were very similar so the airport is probably more convenient. Our airbnb also exchanged money for us and accepted Euros and USD! However this is probably rare,  so I wouldn’t count on it. We brought around $1000 for 2 people for 5 days and used almost all of it.


Get ready to post some #latergrams because wifi is limited and by limited I mean basically non-existent. I saw signs for wifi in some cafes and bars but apparently you still had to pay for it and it is spotty. Prepare by downloading maps and info before you leave your wifi comfort zone. Embrace the local culture and unplug for a few days, you’ll survive I promise.

Grant and Rachel in Havana


You need it! Download a dictionary on your phone and think back to your high school Spanish conjugations because most of the locals we encountered did not speak English. They were all gracious with us as we are learning and it was an awesome experience to practice.


We were told to get to the airport 3 hours in advance by nearly everyone we asked. My go to arrival time is 2 hours for international travel so this seemed a little excessive but everyone was pretty adamant about it so we did as suggested. Big mistake! Not only is the airport tiny and security was easy breezy but it doesn’t have air-conditioning! Sitting in a crowded terminal without AC for over 2 hours seemed like a death wish so we payed $25USD to go to the Cuban version of an airline lounge. It was called Cuba VIP or something like that and included wifi (the first we used!), snacks, and drinks. I recommend not getting to the airport as early. Or if you are stressed about it, get there 3 hours in advance and go to the VIP room. They also changed our boarding gate unannounced so be aware of any flight changes.

Beat the Heat

Granted we did visit in July, but OMG it literally felt like we were inside an oven. Be prepared to sweat! Pack lots of sunscreen and bottled water.

Conservative Culture

Cuba seemed fairly conservative so be mindful in certain areas. Grant wasn’t allowed in the bank because his shorts were too short, and our friends got stopped and reprimanded for jogging with their shirts off on the Malecón!

Old Car in Vinales Cuba


I expected there to be more crime or sketchiness but we felt safe the entire time. The Cuban people are lovely. They are so kind and fun and really appreciative of the tourism. So get your “people to people education” on and hang with some locals!

While Cuba appears to be a tropical wonderland filled with salsa, mojitos, and cigars it has its challenges just like anywhere else. Do your research, be prepared, and you will have an amazing time.

For more information on Cuba, grab this Lonely Planet guide book.

Viva Cuba,



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