How to Book Trip to Cuba from the U.S.

March 6, 2018

We went to Cuba for two glorious weeks of exploring all corners of the island last year. It was such an exciting trip that I implore everyone with the means to go. During our last week there, President Trump decided to tighten travel sanctions for US citizens to Cuba and it caused such a stir and lot of conversation everywhere we went.

Since President Obama lightened the sanctions against Cuba, there’s been an influx of American tourists visiting the Caribbean island for the first time in decades.¬† JetBlue had a good deal on flights to Havana, Cuba for about $215 so T and I snagged two round trip tickets with the intention of exploring the island for two weeks.

Over the past seven months, I scoured countless online forums, Facebook groups and blogs to learn more about navigating the Cuba and how to enjoy a vacay there without knowing a lick of Spanish, the official language. Several Facebook friends have asked me to elaborate on the trip booking process so here I go…

When you book your flight, you’ll be asked for the reason for your trip. There are 12 different categories for travel. I chose journalism because I plan on blogging about my trip extensively. Most people choose the People-to-People travel, which is not only a legal way for Americans to visit Cuba. JetBlue sent us a form to fill out online and submit to them. You will need a visa to enter and exit Cuba. You can buy the tourist visa for $50 at the airport on the day of your flight.


  1. family visits
  2. official business of the U.S. government, foreign governments, and certain intergovernmental organizations
  3. journalistic activity
  4. professional research and professional meetings
  5. educational activities
  6. religious activities
  7. public performances, clinics, workshops, athletic and other competitions, and exhibitions
  8. support for the Cuban people
  9. humanitarian projects
  10. activities of private foundations or research or educational institutes
  11. exportation, importation, or transmission of information or information materials
  12. certain authorized export transactions

If you fit into one of these categories you qualify for a general license. There is no need to apply for a specific license through the Office of Foreign Assets Control.

Trump doesn’t want American dollars going to the Cuban Military anymore, which he says is guilty of humanitarian violations to the Cuban people. The gist of the new policy is that Americans can still travel to Cuba but can no longer select the “people-to-people” or educational travel classification for the purpose of travel. Instead we have to select a new category called “Support for the Cuban People” and keep an itinerary of your travel just in case you’re ever audited.

But Trump’s announced policy means Americans won’t be able to stay in Cuban hotels, rent cars or take buses at all since the Cuban government owns them. Approved group travel through tour operators will remain legal if you are booked to stay in pre-approved accommodations such as privately owned hotels, bed and breakfasts or a casa de particular (a homestay with a Cuban family) and AirBnBs.

Arrive at least 2 hours before your flight. If traveling on JetBlue, make sure you get dropped off at Terminal 5. Once you enter the airport, you will see signs on your left side for Cuba Check-In. Yes, there’s a special cue just for Cuban tourists. Take the elevator or escalator downstairs and follow the signs around to your right to get to the Cuba Check-In Counter. Make sure to have your passport ready.

The customer service representative will charge you $50 per Cuba Tourist Travel Visa. You will be given a card to fill out. Make sure to fill out both sides, one in English, the other in Spanish. Hand over your luggage if you’re checking any and proceed to the TSA security checkpoint. After screening, head to your gate and wait for your flight.

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