Plan Your Cuba Trip Now, Here’s How

With President Obama’s recent trip to Cuba — the first for a sitting US president in 88 years — even more Americans are considering making their own trip to Cuba. It can still be a little challenging to visit, but with a little bit of advanced planning, a trip to Cuba is full of rewards. Here’s what you need to know about planning your trip.

Determine why you’re going

Unlike a trip to other countries, the US government currently requires you to have one of 12 government-approved reasons to travel to the island:

  •         Family visits
  •         Official business on behalf of the US government
  •         Journalism
  •         Professional meetings or research
  •         Educational activities
  •         Religious activities
  •         Public performances, workshops, athletic competitions, clinics and exhibitions
  •         Support for the Cuban people
  •         Humanitarian projects
  •         Activities on behalf of educational institutes or private foundations
  •         Exportation, importation or transmission of information materials
  •         Certain transactions exporting goods that are authorized under federal regulations 

Travel for purely touristic reasons is still not allowed, so that means you’ll have to keep some documentation of your time in Cuba. The good news is these new regulations are pretty loosely defined, so you should be able to find a category under which to travel pretty easily. Be prepared: You’ll have to declare your reason for traveling to Cuba when you book your flight.

Make an itinerary

To prove that you’re traveling to Cuba for your stated reason, you should develop your itinerary early, but that’s pretty easy. For example, writer Johnny Harris said that he met a couple on their way to Cuba who were traveling under the professional research category. “He is a musician, she an architect,” wrote Harris. “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 new inclusive and intentionally broad language of the authorized categories of travel to Cuba means you can easily travel to the island without being dishonest or deceptive.

Plan to keep all of your receipts

Sounds like filing your taxes, doesn’t it? Cuban travel expert Brendan Sainsbury told BuzzFeed that travelers should keep the receipts from their Cuban trip for five years as proof that they went to Cuba for their stated reason and not just for partying. “It’s hard to say exactly how the government checks on this,” Sainsbury told BuzzFeed. “But the Department of Treasury and Commerce might catch up with you if you just make something up and off you go.”

Figure out your travel logistics

This January, Cuba and the US decided that US airlines will offer 110 commercial flights to Cuba every day, but we’re still waiting on those. In the meantime, you can book your flights online, but you just have to do it through approved travel services. Some reliable sources to look into are Marazul, Intrepid Travel, Classic Journeys, ABC Charters and Cuba Travel Services. If you want to book your own travel, you have to fly through another country first, such as Mexico. You still have to meet one of the 12 authorized requirements for travel listed above, though.

There’s also a matter of hotel stays

As Classic Journeys CEO Edward Piegza warns, “Tourism is up 75 percent, and there is zero new infrastructure — meaning there’s a lot of demand without the infrastructure to support it.” For instance, José Marti International Airport in Havana has added 20 new flights per day but was already running at full capacity before that. Hotels can be hard to find, too, so definitely nail down your accommodations early. Consider homestay options such as Airbnb, now available in Cuba, to enjoy more bang for your buck.

While all of this may sound daunting, most Americans can find a reason to travel to Cuba under the authorized categories. No one scrutinizes your visa either, so all you have to do is get a little creative with your reason for setting off to the island. Prepare an itinerary ahead of time and be ready to keep up with some paperwork. The reward for a little work and preparation may just be the time of your life. 

—Megan Winkler

Megan Winkler is an author, historian, Neurosculpting® meditation coach, certified nutritional consultant and DIY diva. When she’s not writing or teaching a class, Megan can be found in the water, on a yoga mat, learning a new instrument or singing karaoke. Her passion for a healthy mind-body-spirit relationship motivates her to explore all the natural world has to offer.



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