U.S. Tour Operators Proceed Carefully on Cuba Trips With Eye on 2024 Elections

Skift Take

U.S. tour operators may not have long to take advantage of the eased travel restrictions to Cuba. So they’re not wasting time during their preparations because legally taking travelers to the island is very complicated.

Rashaad Jorden

The Biden administration’s decision earlier this month to ease some travel restrictions to Cuba enacted under former President Donald Trump has U.S.-based tour operators making plans to run more trips for Americans on the island — or in some cases, return to the popular Caribbean destination.

But tour operators are also treading cautiously during their preparations, with such companies aware that travel to Cuba could again be significantly curtailed after the results of the 2024 U.S. presidential election.

“This is sort of a volatile destination in terms of it remaining open for travel,” said Jeff Roy, the executive vice president of Collette, about the possibility of running trips again in Cuba.

The Rhode Island-based tour operator took, on average, between 500 to 1,000 U.S. travelers to the country annually between 2012 and 2018. Former President Barack Obama relaxed travel restrictions to Cuba in 2011, which enabled companies like Collette to run trips for Americans on the island.

“We’re at a point now where we’re moving a lot of volume and there’s still a lot of work with all of the U.S.-(enacted) Covid travel restrictions. To distract ourselves from that right now to move right over to Cuba with the risk that it would be gone in two years (is) something we have to contemplate — risk and reward for that product.”

The company shelved its Cuba tours after the Trump administration ended authorization in 2019 for group educational trips, which have been referred to as “people-to-people” travel due to the U.S. government’s stated goal of having American travelers engage in cultural and educational interactions with Cuba’s citizens. But the Biden administration is permitting those trips to resume, enabling licensed tour operators and travel companies approved by the U.S. government to conduct organized group tours to Cuba. Educational trips fall under the 12 categories for authorized travel from the U.S. to the island.

“The (new) policy will hopefully be permanent,” Roy said. “We ended up having to cancel (after the Trump administration’s decision) a lot of departures and trips that (customers) had been planning for a long time. And we’d hate to have to do that again to our customers.”

Challenges in Taking Guests to Cuba

Roy acknowledged major hurdles Collette faces in resuming trips to Cuba. “There are usually a bevy of reporting requirements to the U.S. government that have to be followed,” Roy said, stating that entire itineraries must be approved even before his company can offer tours to Cuba.

He admitted the earliest Collette would likely run tours to Cuba is 2024 as the company is in the early stages of designing its trips for May of that year to April 2025, a month by which U.S. policy could have changed.

“We really haven’t decided how we’ll move forward with Cuba yet. But clearly there are some challenges here,” Roy said, adding Collette hasn’t established a clear timeframe for a final decision but would examine this summer, among other things, the likelihood of stability regarding Cuba’s opening.

Peggy Goldman, the president of Pennsylvania-based tour operator Friendly Planet Travel, also admitted time is of the essence regarding Cuba. The company has a license to run people-to-people trips, but it’s waiting on approval to use it from the Office of Foreign Assets Control, the U.S. Treasury Department agency that grants licenses for travel to Cuba. Friendly Planet has taken U.S. citizens to the country under the Support for the Cuban People Program, another category for legal travel.

But Goldman argues that people-to-people trips are easier to put together for travelers in contrast to those under the Support for the Cuban People Program, which bans Americans from spending money owned by the Cuban government. She said she hopes the U.S. government will allow its citizens to stay in hotels in Cuba again, which are either fully owned by the government or are operated as a joint venture with a foreign company.

Guests on trips Friendly Planet run under the Support for the Cuban People Program stay in casa particulares, privately-owned residences as regulations enacted by the Trump administration made it more difficult for U.S. travelers to stay at Cuban hotels.

“We can’t use hotels because you can’t stay in a place that’s going to supply revenue to the government or the military. There are no hotels that I know of that we could use,” Goldman said, highlighting Gaviota, a major Cuban hotel company run by the military.

“We have to use the bed-and-breakfasts, which is a big problem. If you want to bring a group to Cuba of 12 to 14 people outside of Havana, you have to stay in multiple houses. And it’s just unwieldy.”

A Major Reason For Optimism

However, Goldman is buoyed by the Biden administration’s move to allow U.S. airlines to fly to Cuban cities outside of Havana, which she believes will enable Friendly Planet to conduct more tours in a country with very few highways.

“The return of these flights to multiple cities in Cuba is big. Having those flights back will open up additional sights for us,” Goldman said, adding that her company plans to take travelers to more locations in eastern Cuba. Friendly Planet could run trips to new destinations in Cuba by the end of 2022, depending on when it receives information from U.S. airlines about flights to cities outside of Havana.

“It’ll make a huge difference for us to be able to put back those tours for people who have the time and resources to explore the whole island, as opposed just to a little piece of it.”

While Roy expressed uncertainty regarding U.S. carriers making significant investments in flights to Cuba, which he said would be a factor in Collette’s decision about the country, he is enormously confident there’s a pent-up demand for travel to the island.

“There’s plenty of people who want to go to Cuba if allowed. It’s no different from people who have wanted to go to Australia and New Zealand for the last couple of years,” Roy said.