Cuba Within Reach

Restrictions on travel to Cuba have continued to loosen since President Obama first announced, in December 2014, that the U.S. would be restoring diplomatic relations with the country. In March 2016, it became legal for Americans to travel to Cuba as individuals rather than being required to travel as part of a group.

But don’t pack your bags just yet—you still can’t quickly hop on a flight to Havana. If visiting Cuba fills your travel bucket dreams, here are some ideas on how to start planning.

Authorized Travel Categories

You used to need a specific license from the Treasury Department’s Office of Foreign Assets Control to travel to Cuba, a process that could take months. Now, anyone who falls under one of these 12 categories is eligible to apply for a general license, involving far less wait time and paperwork:

1. Attending a public performance, clinic, workshop, exhibition or athletic competition. Imagine traveling for the Havana Art Biennial at the end of May or the Havana Marathon/Half Marathon in November!

2. Journalism

3. Professional research and meetings

4. Educational activities

5. Religious activities

6. Certain export transactions

7. Humanitarian projects

8. Activities of private foundations or research for educational institutes

9. Exporting or importing information or “information materials.”

10. Travel related to some authorized export transactions

11. Family visits

12. Official government business.


With all these categories, just about everyone could find a justifiable reason to visit Cuba. But there are still other obstacles. Getting a flight requires some research, with direct flights to Cuba being offered through charter companies and not bookable through online sites like Travelocity or Orbitz, though major airlines could start offering direct flights as early as summer 2016.

Maybe you’ve heard the buzz about Airbnb coming to Cuba and are wondering if you could just book your own bed and breakfast? Technically the answer is yes, though travel agents advise the safest and easiest way to visit Cuba is still via a “people-to-people” tour. And you’d still need to be traveling under one of the U.S. government’s 12 approved travel categories to use Airbnb’s service. Spotty internet service on the island can also make booking your own hotel room tough.

The easiest, although more expensive, way to visit Cuba legally is on a “people-to-people” tour. People-to-people trips can only be booked through tour operators that have obtained a license from the Treasury Department’s Office of Foreign Assets Control. As one would expect, people-to-people travel actually requires meeting up with Cuban citizens, say artists or scholars, not just relaxing poolside at your resort. Think of this vacation as more tropical adventure, less tropical paradise.

Reputable People-to-People Tours:


Since 2000, more than 10,000 guests have toured Cuba with New York based InsightCuba. They offer more than 150 departures annually, including plenty of specialty tours, geared towards specific hobbies and interests. “We’re finally coming up for some air,” InsightCuba’s president, Tom Popper, said in the weeks following the 2014 restoration of relations. “Since President Obama’s announcement on December 17, our web traffic remains six times normal, inquiries are up four times, and weekly bookings are tripling last year’s figures.”

National Geographic Expeditions has also offered a Cuba trip for several years. “A few things make it different from the others,” says Norie Quintos, acting editor-in-chief of National Geographic Traveler magazine. “Number one, you’re connecting with real Cubans—musicians, historians, entrepreneurs. Secondly, you’re guided by NG experts such as geographer Juan Valdez, a refugee from Cuba. Finally, you’re going with a group with established relationships to the island, which really means you’re staying in the best accommodations and visiting the most interesting places.”

Here are Quintos’ tips for choosing a good people-to-people tour group to Cuba:

1. There will likely be many new operators to pop up, hoping to cash in on Cuba’s popularity. Go with an operator that has established relationships.

2. Don’t just compare the listed tour price; find out what’s included and what’s extra. For example, some companies won’t cover all meals.

3. The right guide makes all the difference. Who is leading the trip and how much do they know about the island? Ask beforehand.

For now, a call to your local travel agent is a good place to start. They can help you decipher the regulations and restrictions about traveling to Cuba. This list of frequently asked questions from the U.S. Treasury’s Office of Foreign Assets Control might also come in handy. Just keep in mind these travel restrictions could be changing soon or disappearing entirely.

What to Do:

Kendra Thorton, president and owner of Royal Travel and Tours, based in Winnetka, says Cuba is one of her agency’s most sought-after destinations this year. Here are a few of her must-see and -do recommendations in Havana:

  • Visit La Habana Vieja (old Havana), a UNESCO World Heritage Site, particularly the Cathedral Square, Plaza de Armas, and the San Francisco Square.
  • The top two museums in the city, per Thornton, are Palacio de los Capitanes Generales, the former home of the governor of Cuba during colonial times, and the Museum of Fine Arts (note that there are two separate buildings–the one you want to see is the museum dedicated to Cuban art collections, which have never been seen outside of Cuba).

Where to Eat:

  • The Floridita bar and restaurant, located near Finca Vigia, Ernest Hemingway‘s former residence, was one of his popular haunts.
  • Tropicana and Bodeguita are two other popular restaurants that provide colorful entertainment and authentic Cuban culture.

Where to Stay:

  • Hotel Saratoga, which Thornton says has the “best service, best room product, and a wonderful rooftop pool with great views of the city.”
  • Thorton also recommends the Parque Central Hotel in Havana, but cautions against staying at the Hotel Nacional, Havana’s most famous hotel. “The rooms are very tired and in dire need of renovation,” she says.

Ready to say “Hola” to Havana? Buena suerte (good luck!) and start planning now.

Updated on May 2, 2016. 

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