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Here’s how to travel to Cuba

Traveling to Cuba isn’t hard anymore

It used to be difficult, but now it’s not. In January, President Obama announced a “new course” with Cuba that included an easing of many restrictions banning Americans from traveling to the island.

You still can’t go as a straight-up tourist, but there are now 12 broad categories under which an American can travel to Cuba. And you no longer need to apply for a license and wait to get approval. You now just buy your ticket online and declare which of the 12 categories your trip falls under. All of this happens on an easy-to-use website. There’s no application or waiting period. Be warned, however, that charter flights are still painfully expensive (around $500 from Miami to Havana).

Cuba View

What are these 12 categories, and do I fit into any of them?

The Obama administration outlined the following categories for legal travel to Cuba:

  1. Family visits
  2. Official business of the US government, foreign governments, and certain intergovernmental organizations
  3. Journalistic activity (this requires an extra license)
  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 export transactions that may be considered for authorization under existing regulations and guidelines

Read details about each category.


    If you’re looking to just lie on a beach, you still aren’t allowed to travel to Cuba. But if your idea of good travel is connecting with people and learning about a culture, you could be there next week.

    I sat next to a couple on my flight to Havana who were going to Cuba under the “professional research” category. He is a musician, she an architect. Their itinerary was packed with visits to museums, concerts, and historic buildings in Havana. They saw this as a trip that would provide inspiration and education for their work. The official language for this category makes you affirm that you are a “full-time professional whose travel transactions are directly related to my profession, professional background, or area of expertise.” These two were qualified for the category and had no problem getting a visa.

    Get creative

    “Almost every American should be able to travel to Cuba under one of these categories,” Sen. Jeff Flake, a major sponsor of the new policy, told me last month. One lawyer who specializes in Cuba-US issues told the New York Times that if you can’t think up an itinerary that fits into one of the 12 categories, “you’re not trying.” This doesn’t mean you need to be deceptive or dishonest. Instead, you can build a trip around the broad and inclusive language of the new regulations. Be forthright about the reason of your trip, and be ready to show an itinerary in the unlikely event that an American customs worker asks you for one.

    The categories all contain the qualifier that your time in Cuba will not “include free time or recreation in excess of that consistent with a full-time schedule.”

    The language is meant to discourage lolling on the beach and lazily sipping mojitos at your hotel bar. As long as you have productive plans that fall within your category of choice, you can honestly certify that your travel is legal, even if you take a couple of extra hours to absorb the view while visiting the historic Morro Castle.

    Morro Castle

    You can also pay someone else to do the creative thinking for you: People to People Tours — in which you are bused around the island and guided through some educational exposure to Cuban culture — are becoming popular among Americans. They can be expensive, but are structured and often include lodging and food. Take a look at an example itinerary.

    You have your itinerary — now what?

    It’s simpler than you think. Go to cheapair.com and buy a ticket. While booking, you’ll check a box certifying that you’re traveling under one of the 12 categories. There are numerous flights every day from New York, Tampa, or Miami to Havana through several charter companies.

    Once you book, you will get an email that will require you to submit a few things (a copy of your passport, a few forms, and $30 for the visa). You can either have your visa sent to you or opt to pick it up at the airport. There’s no waiting for approval or anyone scrutinizing your itinerary to make sure it’s acceptable. Your visa is automatically granted upon buying the ticket and submitting your documents.


    The one caveat here is price. There is not yet a robust market of American flights to Cuba, so prices are high. You’ll pay around $500 for the 42-minute flight from Miami to Havana. Painful. But you will make it up on the other side, where you can stay comfortably for $25 per night and eat well for $10 a day.

    A few tips

    Do yourself a favor and don’t stay in a hotel. There is a thriving market of private homestay options. People open their homes to visitors for an average of $25 a night. Airbnb now works on the island and is an efficient way to pin down a reservation for a private home (called a casa particular). If you are staying in Havana, a good place to stay is the Old City (La Habana Vieja), where the alleys are narrow and tall and the colonial residences are absolutely stunning.

    Habana Vieja

    My final tip is more of a lamentation: It turns out the Cuban government owns most street food operations in Havana. And after a day of exploring food options, it will be clear that the government doesn’t have culinary excellence at the top of its central planning agenda. So you’re left with a few dismal options, mainly white bread rolls with lunchmeat or flat bread with a cheese-like substance akin to what you find on top of baseball stadium nachos. They call this latter option “pizza.”

    I was lucky to stumble upon a tiny private restaurant tucked deep into a residential neighborhood in Central Havana. The food was markedly superior to the state-run options, and I ate there every day. But your options while roaming the streets are limited. Good luck.


    Travel to Cuba is easy for Americans who are interested in making it a cultural or educational experience. While the embargo is still in place, the American government is opening the door for easier access to the country. If you’re up for a little extra planning, there’s no reason Cuba can’t be your next travel spot.

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