Travel To Cuba Just Got Easier, As U.S. Lifts Trump-Era Flight Restrictions

It just got easier for Americans to fly to Cuba. On Wednesday, at the request of Secretary of State Antony Blinken, the U.S. Department of Transportation lifted civil aviation restrictions on flights between the U.S. and Cuba established during the Trump administration. Those restrictions had prevented U.S. commercial and chartered flights from flying to Cuban cities other than Havana.

“Scheduled and charter air services between the United States and Cuban airports may resume effective immediately,” wrote Blinken in a letter to Transportation Secretary Pete Buttigieg.

In practice, though, how easy it will be to travel to Cuba for a leisure trip is a question mark. For Americans, the past decade has seen wide swings in U.S. foreign policy that have whiplashed travel rules.

President Obama began relaxing rules for to travel in Cuba in 2011. By the mid 2010s, U.S. leisure travelers could visit the island if their trip fell under specific categories, including organized cultural group “people-to-people” trips. Mind you, it was very hard to find a place to stay, since U.S. travelers were prohibited from patronizing businesses owned by the Cuban government, which owns most of the country’s hotels.

The easiest workaround was to take a cruise. Cuba quickly became a hot stopover on sailings that offered onshore excursions that ostensibly fell into the “people-to-people” category. While the largest cruise lines — Carnival Cruise Line, Royal Caribbean International, Norwegian Cruise Line and MSC Cruises — docked in Havana, a number of smaller, upscale cruise operators created more Cuba-centric itineraries making calls on smaller cities like Cienfuegos, a colonial hub on the southern coast, and Santiago de Cuba, the island’s second largest city. By 2018, more than a dozen cruise lines were bringing roughly 800,000 passengers to Cuba annually.

In 2019, the Trump administration drastically rolled back leisure travel to Cuba by banning commercial and chartered flights from the U.S. to Cuban cities other than Havana. U.S. cruise ships were prohibited from stopping in Cuba and the “people-to-people” travel category was eliminated.

Killing “people-to-people” trips meant that, while Americans could legally fly into Havana, they had to find another category — family visits, professional trips, religious or humanitarian work or, what became the most popular option, a category called “support for the Cuban people.” For the latter, travelers need to demonstrate that their plans include activities like meeting with local business owners, visiting museums or galleries, and eating at locally owned restaurants and markets — not always easy to arrange without a tour operator or guide, never mind the problem of finding accommodation that’s not on the prohibited list.

Now the Biden administration is trying to swing the pendulum back. Two weeks ago, officials announced initial steps to reopen limited leisure travel to Cuba. “We’ll certainly ensure travel is purposeful and in accordance with U.S. law,” said a senior White House official. “We are reinstating group people-to-people educational travel under a general license.”

A year after anti-government protests in Cuba, the Biden administration says making travel easier is a key to building cross-cultural bridges. “We’ll note something that President Biden had said often, which is his belief that Americans are the best ambassadors for democratic values,” said the White House official. “And facilitating group people-to-people travel will allow for greater engagement between the American people and the promotion of their democratic values.”

But moving forward, once-bitten-twice-shy travel companies will need to be more mindful of what qualifies as legitimate “people-to-people” travel as opposed to flat-out tourism.

In March 2022, a federal judge rejected claims by the four largest cruise companies — Carnival, Royal Caribbean, Norwegian and MSC — that they engaged in lawful travel in Cuba. In a 169-page ruling, U.S. District Judge Beth Bloom, an Obama appointee in Southern Florida, concluded that the cruises lines had offered excursions that “constituted tourist activities and not proper people-to-people activities, paying millions of dollars to the Cuban Government to engage in impermissible travel” while docked in Havana, reported Travel Weekly.

It remains to be seen how quickly and enthusiastically cruise lines and tour operators will reinstate Cuba trips this time around, given how the rug was pulled out on them before, and with the 2024 U.S. presidential election looming over the horizon.