Cuba has long been on our must-see places. We originally wanted to go in 2017, but uncertainty over rule changes made us postpone the trip. Finally in the summer of 2019 we decided to buy the tickets.It wasn’t without hassle and requires a detail-oriented person, but it was well worth it.
We were going to be in New York for the New Year. We wanted to spend some time with family then fly out on JetBlue to Santa Clara. Our plan was to start in the center of the island and then make our way west toward Havana and leave on Delta there. The tickets were cheaper and places to stay were better priced in Havana further away from the holiday.
Unfortunately, in October 2019, the U.S. banned flights from the U.S. to any Cuban city other than Havana. JetBlue gave us the option to either rebook to their non-stop to Havana at no extra cost or get a refund. We would have come out ahead by a few dollars by sliding over to the Havana flight, but decided to take a refund and rebook a day earlier since the changes meant an extra half-day of ground transportation in Cuba that we weren’t expecting.
United had a better deal than JetBlue and I get two free checked bags on United. It was a no brainer for the two of us, but I needed four tickets with four checked bags. Then I noticed Business Class tickets were just $54 more than a regular ticket and it includes two free bags and a meal. The most frugal option would have been to just upgrade one person because, after accounting for traditional bag fees, we would have come out ahead $6, but we paid to put two family members in the front since it wasn’t much more.
As you book your ticket, the airline website will ask the reason for your travel and you’ll need to select one of 11 OFAC-approved reasons for going to Cuba. We selected “support for the Cuban people.” There is no documentation required when booking your ticket to prove your reasoning. However, you must keep proof that you met the OFAC guidelines for five years after your return.
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United's Cuba desk at Newark |
The check-in experience to Cuba varies by airline. At Newark, United tucks away a “Cuba desk” at the far west corner of baggage claim. It features an inefficient system to get you underway. Here’s how it works:
After you enter the stanchions, a United employee sitting off to the side at an unmarked podium will then pull you out of line to check your passport.
If you don’t have a visa (aka tourist card) from the Cuban government, one person from your group will need to go to the far right end of the desk and purchase one for everyone in your party (side note: United allows Cuba Travel Services to issue the visa, which charges an extra $25 on top of the $50 for the visa. It’s annoying to pay such a high fee when JetBlue, Southwest and Delta just charge $50). Don’t try to be sneaky and use a (cheaper) green tourist card that the rest of the world uses. All passengers on flights from the U.S., regardless of nationality, must use a pink tourist card.
Visa in hand, you can then rejoin the rest of your group who will have been making their way through the line.
An agent will then call you up to check you in. The experience is much like any other check-in desk, except after they tag your bags a man pushing a Smarte Carte, who isn’t prominently wearing a required airport ID and who’s only clothing that identifies him as an employee is a well-worn United hat, will come up and take your suitcase. I’m not sure where he takes it, but the luggage ended up in Havana.
If you’re connecting from another United flight, you will be required to purchase your visa from a CTS representative at the gate.
United usually has Republic fly an E-175 to Havana, but we took a rare mainline flight. It was about half-empty, but was booked completely full on the way back. United doesn’t overnight crews in Cuba, so the same group that brought us down would work the return. They also send an engineer to help with any issues, monitor ground staff and check all fluids that are put into the plane in Havana.
As we flew over North Carolina, a flight attendant came through with three forms: 1) “international debarkation,” 2) health declaration and 3) customs declaration. I also figured it was a good time to fill out my visa.
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A pink Cuba visa from CTS |
I started with the tourist card, which is ironic because the U.S. explicitly forbids tourism, but to the Cuban government...you’re a tourist. Make sure to fill out the form exactly as told because you’ll need to buy a new one if you make a mistake. With my luck, we hit a slight bump as I was writing, so one of my passport numbers looked odd. I tried to fix it and prayed immigration didn’t care. Spoiler: they didn’t.
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Cuba declarations form |
I then moved on to the declaration. It was very straight forward until I got to the question about “equipment and items (electrical appliances).” I read online they are referring to things like refrigerators and toasters not hair dryers otherwise I might have put it down.
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Don't forget the back side! |
The only thing I saw Customs really inspecting was cameras, our hair dryer didn’t even rate a look.
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Cuba health form |
The health form was also very easy. They just asked if you’ve felt ill recently. After clearing customs and passport control, there are people dressed like nurses waiting to collect the forms. I didn’t see them giving anyone a cursory look.
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Cuba debarkation form |
Finally, I moved onto the debarkation form, which was my nemesis. I was so paranoid about making a mistake that I kept making them. I must have gone through at least three. Once I didn’t realize there were boxes for the information, so I wrote everything underneath. On another I made the mistake again with the citizenship question and on a third I wrote the address where we were staying on the wrong line. The flight attendant must have thought I was crazy, but I didn’t want to make a mistake. In the end, customs never even collected it.
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Havana's Terminal 2 |
Once we were in Cuba, we did our best to document any time we spent money. When possible, we got a receipt. Unfortunately, that’s not always an option so sometimes we took pictures of private restaurants or shops. Certainly some of it is on the honor system, but we tried to bring back as much proof as possible and stored it away in a safe place for the next five years.