You Can Still Legally Travel to Cuba — Here's How

Colorful buildings in Old Havana.

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Cuba has something for everyone. The island is known for cigars, beaches, and classic cars — but it's also home to a burgeoning culinary scene, excellent mountain climbing and scuba diving, and world-class music and dancing.

Americans began to get a taste of this diversity under President Obama, whose administration relaxed restrictions on travel to Cuba. The island swelled with yankees, and the tourism uptick earned Cuba the title of Travel + Leisure Destination of the Year in 2015. But recent Trump administration policies — like a ban on cruise ships and the elimination of the group people-to-people visa category — have created some confusion about whether it’s okay for Americans to visit. 

Lines at José Martí International Airport in Havana.

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Still, the largest island in the Caribbean remains open for business. You just have to plan your travel strategically. 

Twelve visa categories remain for legal travel to Cuba, ranging from family visits and religious activities to journalistic activity and humanitarian projects. For most travelers, the best fit is the “Support for the Cuban People” category, which requires that travelers engage in a “full-time schedule” of activities that “enhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people's independence from Cuban authorities.”  

While “full-time schedule” is not defined, and specific permitted activities are not indicated, the U.S. Treasury has explicitly stated that “travel to Cuba for tourist activities” is not permitted — and that a “traveler’s schedule of activities must not include free time or recreation in excess.” While this means that an all-inclusive beach resort vacation isn’t in the cards any time soon, it’s probably not going to get in the way of your next trip.

Current U.S. policy prohibits Americans from spending money at establishments — hotels, tour agencies, marinas, stores — owned by the Cuban military. (Find a complete list of prohibited entities here.) Note that, though all hotels in Cuba are at least partially owned by the Cuban government, not all of them are owned by the Cuban military. Unfortunately, some of the nicest properties, such as the Gran Hotel Manzana Kempinski and the Iberostar Grand Packard, are on the no-go list. Airbnb can make it easier to find privately-run homes, but be aware that using the platform for Cuba travel can involve some hiccups.

The best way to adhere to the new restrictions, which are admittedly vague, is staying at privately run guest houses (casas particulares), eating in privately-owned restaurants (paladares), and ensuring that your money goes directly into the hands of local Cubans through activities like walking tours, bike rides, and cooking or dance classes. In recent years, the travel industry has shifted in this direction anyway — so many tour operators, including my own, EscapingNY, are able to continue bringing Americans to Cuba with minimal to no itinerary changes.

A beach in Varadero, in western Cuba.

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Planning your own legal trip to Cuba is possible, but solo travelers should read all U.S. State Department and Treasury documents carefully or hire a professional travel agency to plan their itinerary. Travelers are required to keep a record of their itinerary for five years, during which time the U.S. government reserves the right to audit (and fine) them. Many tour operators keep copies of travel records on behalf of their clients and could provide them in the event of an audit.

I’ve explored every province in Cuba, both before and after these recent restrictions, while leading group tours and doing research for my forthcoming guidebook, Cuba by Bike. Cuba is one of the most beautiful countries in the world, and the Cuban people are kind, generous, and welcoming. This erosion to traveler freedom will surely discourage some Americans from visiting the island — which is not only their loss, but a blow to many in Cuba, where wages in state jobs hover around $25 per month but travel guides and inkeepers can earn several hundred dollars in a single day. Luckily, the "Support for the Cuban People" visa can help you put your money into the hands of those who need it.

One Third of U.S. Workers Haven't Taken a Vacation in More Than 2 Years (Video)

Thirty-six percent of Americans took their last vacation over two years ago, and 51 percent have not vacationed in more than a year, according to the 11th annual Vacation Confidence Index by Allianz Global Assistance.

Many previous studies, from a variety of sources, have shown that Americans, especially younger generations, have a hard time getting out of the office and spending some quality time off. Even though we know vacation is good for our mental and physical health, and some of us even get paid vacation time from our employers, the latest numbers on how many U.S. workers are not taking time off is still, well, depressing.

However, Allianz Global Assistance defines a “vacation” as any trip that is at least a week in a destination that is 100 miles or more from home, so there’s no accounting for trips like “micro-cations,” which are increasingly growing in popularity amongst Millennials and Gen X workers. That said, a previous study identified the ideal vacation length as eight days, and for many people that's not happening.

It doesn’t look like 2019 will be a good year for vacation either. According to Allianz Global Assistance, only 42 percent of respondents said they felt confident they would be able to take a vacation this year — the lowest since 2013.

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You can probably blame all the usual suspects for this vacation deficit as well. Forty-four percent said money was the main reason why they couldn’t take time off, and 19 percent said they wouldn’t want to spend on vacation anyway. Another 12 percent of workers said they didn’t want to take the time off of work. Other reasons include other personal obligations that get in the way of taking time off and the stress of planning a vacation.

But it’s not just employees who are overworking themselves, it’s also the employers. The survey also revealed that 52 percent of U.S. workers say they take about the same amount of vacation time as their bosses do. So, bosses, if you want your employees to use their PTO, you’re going to have to leave the office, too, sometimes. The survey showed Americans are only using 41 percent of their paid time off, while their bosses are using 51 percent.

The survey concludes that American vacations are changing – so much so that week-long vacations could go out of style. Allianz Global Assistance noted that short trips may become even more popular in the future, especially when it comes to making getting away — even for a day or two — more accessible for younger workers.