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Havana Nights: Traveling to Cuba

Temper Your Expectations

Travel companies are betting that the United States eventually will have normal relations with Cuba. That would mean traveling to the long-forbidden Caribbean island would be no different than traveling to Jamaica. For now, however, if you want to travel to Cuba, you still have to follow regulations and temper your expectations for resort-like accommodations.

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As soon as President Barack Obama and President Raúl Castro of Cuba announced in December 2014 that they were restoring diplomatic ties between the two countries, Tom Popper saw the effect on his business. “Our phones started ringing off the hook,” says the president of insightCuba, which books tours to the island nation.

Now, Americans are returning to the long-forbidden country that was a hot destination before the communist takeover in 1959. At the August 2015 flag-raising ceremony that marked the reopening of the U.S. embassy in Havana after 54 years, Secretary of State John Kerry noted that visits by Americans increased 35 percent since January 2015.

Once again, Cuba is attracting American travelers, but going to Cuba literally is no day at the beach. “You’re not allowed to do tourism—you have to have a purpose for going there,” says Adolfo Nodal of Cuba Tours and Travel.

That was true before Treasury Department’s Office of Foreign Assets Control (OFAC) loosened travel regulations in January 2015. Now, as then, to visit Cuba legally, you have to travel under one of 12 categories that are outlined by OFAC. (See “Legal Reasons to Visit Cuba.) Additional rule changes in September 2015 broadened the number of categories in which people who visit Cuba may bring family members, too.

What’s different today is that you no longer have to have a specific license from the U.S. government, nor do travel-service providers or airlines.

However, travel providers and charter airlines, which still are the only way to fly direct to Cuba from the United States, as of press time, require travelers to fill out a certificate of travel, which the companies must keep for at least 5 years. The certificate lists the 12 travel categories and includes a check box next to each.

“The way the law is now, it is kind of an honor system,” says Jeff Klee, who is the CEO of CheapAir.com, which began to sell charter flights to Cuba in April 2015. “All you have to do is check a box, but if you check a box untruthfully, you’re breaking the law.”

Legal Reasons to Visit Cuba

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It also is illegal to travel to Cuba on a people-to-people cultural exchange of your own making. In other words, you can’t just fly to Cuba and claim that it’s to meet Cubans and learn about their culture. Even though officials won’t check your itinerary or track your activities, travel agents and tour operators tell us, U.S. regulations still allow for unspecified penalties for breaking the rules. For now, if you want to “vacation” in Cuba legally, you have to go on an organized tour.

Furthermore, visiting Cuba isn’t like visiting other Caribbean destinations that have spent decades building up their infrastructure to cater to Americans, say experts and travelers. The amenities that most Americans expect still are lacking.

BY AIR OR BY SEA. As travel restrictions ease, U.S. airlines are expanding—or plan to expand—charter flights to Cuba. JetBlue in July 2015 added a route to Havana from New York City to its existing routes from Fort Lauderdale and Tampa, Florida. American Airlines is expected to add a route to Havana from Los Angeles in December 2015, which builds on its existing charter flights from Miami and Tampa. American expects to operate 1,200 charter flights to Cuba in 2015, which is a 9 percent increase from 2014, according to the Miami Herald.

As of press time, no U.S. airline runs regular commercial flights to Cuba. The airlines and others in the travel industry hope that this situation will change soon, however. “The general feeling is that by sometime in 2016, there will be regularly scheduled flights to Cuba,” Klee says. “Some of the big airlines will fly there in the same way that they fly everywhere else in the Caribbean. There are still some hurdles that have to be jumped through to make that happen.”

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