Under the new regulations, individual Americans travelers will no longer be able to visit the island on what are known as people-to-people trips, a popular mode of travel introduced as part of Mr. Obama’s historic thaw. People-to-people trips will now be permitted only for groups and must be organized by a licensed tour operator.
Americans will also be barred from transactions with companies run by the Cuban military — a potentially significant restriction, given that many of Cuba’s branded hotels are managed by a military-owned conglomerate.
The Treasury Department went some way to clarify the new rules on Friday, writing in a statement that the changes would not apply to people who had already booked trips or to existing business deals with the military.
But the new restrictions would put new properties like the Gran Hotel Manzana, managed by Kempinski Hotels but owned by Gaviota, a Cuban military-run company, off limits to American travelers. Travel representatives said they would redirect American travelers to hotels run by civilian tour organizations, including Gran Caribe and Cubanacan — both of which own several properties in Havana.
Exactly how far those restrictions go, however, is unclear. Could a tour organizer rent a bus from a military-run company? What about purchases from a military-run retail store?
Prohibitions of that scope would make organizing group trips to Cuba “impossible,” said Michael Sykes, president of Cuba Cultural Travel.
Tour operators and Cuba experts predicted that the Cuban government would find loopholes. John Caulfield, who was chief of the United States diplomatic mission to Havana from 2011 to 2014, said the government could move tourism assets into the control of civilian ministries.
“In an economy like Cuba’s, they can rename things and change things around,” he said.
Still, even if the new rules were workable, travel representatives said, tighter regulation would…