Client demand for travel to Cuba has nearly stopped entirely for many travel advisors, a drop they largely attribute to the public's confusion following multiple changes by the Trump administration to the regulations governing travel to the island.

"My business has dropped off significantly since the new administration, because Trump has changed the rules," said Janice Chieffo, a Protravel International advisor based in Laguna Beach, Calif.

A criminal prosecutor until her 2015 retirement, Chieffo first visited Cuba for a law seminar before the Obama administration loosened regulations on travel to the country. Her earlier trips to Cuba sparked a love of the country, and she began organizing trips there in 2015.

Three or four years ago, her phone was "ringing off the hook" for Cuba trips, Chieffo said. Now, client demand is sporadic at best. 

She attributed that drop to the changes the administration has made to travel, including eliminating the people-to-people category of permissible reasons to visit, restricting cruise lines from calling in Cuba, restricting flights between the U.S. and Cuba to Havana only and preventing U.S. citizens from doing business with any entity with ties to the Cuban military.

"My business has virtually stopped," said Chieffo, who has shifted into selling luxury travel to other destinations.

Stephen Scott, a Protravel advisor based in Chicago, has also seen a drop-off in interest from clients. He still gets the occasional request, but interest is much lower than it was a few years ago.

"From my perspective, it all boils down to confusion," he said. "People don't know if they can or cannot go. [If they do decide to go], they don’t know if they will get in trouble later, after new sanctions are put in place."

Mathy Wasserman, manager of Los Angeles-based Flying Giraffe Travel, said the cruise ban “really destroyed most of the business for us,” even though Flying Giraffe mostly booked land tours. The cruise ban colored the public’s perception about whether they could visit Cuba, which affected sales. Now, the latest ban on airlines flying to anywhere in Cuba except Havana is likely to have a similar affect.

"With less accessibility," Wasserman said, "it becomes -- although it is a legally doable thing -- a less interesting thing to do, and I think people feel concerned."

For advisors whose clients have expressed interest in Cuba, navigating the murky restrictions can prove challenging. 

David Lee, owner of luxury tour operator Cultural Cuba, said advisors should be sending clients through a reputable destination management company.

"There are several reasons for this," Lee said, "including the fact that the legalities of going to Cuba are constantly changing and there are requirements that do need to be taken seriously. This is not a book-a-hotel and book-a-transfer destination."

Following a ban on the people-to-people category this past June, the support-for-the-Cuban-people category emerged as the most common option for tour companies. But what that category entails and how it differs from the people-to-people category remain fuzzy.

"People to people was supposed to be a cultural exchange, which is still applicable under support for the Cuban people," Lee said. "The quickest way to explain support for the Cuban people is [to say] the vast majority of the money spent should be going to the people, not the government."

In addition to keeping money out of the Cuban government's coffers, American travelers also need to ensure that they engage "in a full-time schedule of activities" and that their itinerary "does not include free time or recreation in excess of that consistent with a full-time schedule."

According to Lee, the latter stipulation doesn't mean tourists can't enjoy any downtime. Instead, itinerary planning simply needs to be somewhat strategic.

"We don't do a day of nothing planned, but we spread out the free time," Lee said. "A whole day of nothing would be hard to explain. But even if you want to do nothing, you're still going to be doing something. You still have to have lunch, so why not book a cooking-class lunch? That doesn't mean you can't also have time to relax at a rooftop pool."

As was true during the Obama administration, Americans traveling to Cuba are still required to retain documentation from their trip, including receipts and itinerary information, for five years. These records are often kept on behalf of clients by tour operators, a benefit that is proving increasingly useful as the current administration ramps up enforcement efforts.

"Every week, we now get calls from clients who are going for a Global Entry interview, and when they have a Cuba stamp in their passport, they’re asked about their sponsor letter, if they can show an itinerary and what they did there," Lee said. "That has just started happening within the last year and a half."

Despite the hurdles, Lee insists that the support-for-the-Cuban-people category isn't a bad requirement in and of itself. In fact, Cultural Cuba has long used that category for its trips, even before the latest rule changes.

"We don't look at support for the Cuban people as a restriction," Lee said. "If they got rid of the restrictions altogether, we likely wouldn't change anything about our itineraries. If we were to change anything, the only thing we could do differently is send you to a beach for a few days to kick back. But the concept of making sure the majority of funds spent get to the people who so desperately need it, there's nothing wrong with that."

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