Trump Is Weaponizing Lengthy-Standing Restrictions on Freedom to Journey to Cuba

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The administration is concentrating on vacationers who criticize US coverage.

A Russian tourist wearing a shirt with the face of Cuban revolutionary Che Guevara prepares to board a return flight at Jose Marti International Airport in Havana, Cuba, on February 16, 2026.
A Russian vacationer carrying a shirt with the face of Cuban revolutionary Che Guevara prepares to board a return flight at José Martí International Airport in Havana, Cuba, on February 16, 2026. (Yamil Lage / AFP through Getty Images)

The Trump administration has begun to weaponize long-standing restrictions on freedom to journey to Cuba, specializing in vacationers who criticize the US coverage of asphyxiating the Cuban economic system and threatening a navy assault.

The Office of Foreign Assets Control (OFAC)—the arm of the Treasury Department that enforces US financial sanctions towards different nations—has despatched a “request for information” to the advocacy group Code Pink about its participation within the worldwide humanitarian convoy that introduced 500 individuals from greater than 30 nations carrying an estimated 35 tons of meals, medication, photo voltaic panels, and different help to Havana in March. As a part of the convoy, Code Pink chartered a aircraft for 170 individuals that additionally carried 6,300 kilos of medical provides value $433,000 organized by Global Health Partners.

Treasury officers are demanding to know “everything you did while you were in Cuba, who went, how did you go, how did you pay for everything, all the receipts, the detailed description of everything you took for donations…what hotel did you stay in,” Medea Benjamin, cofounder of Code Pink, advised The Nation.

Benjamin suspects the May 21 OFAC inquiry goals to quell dissent towards President Donald Trump’s more and more harsh strategy to Cuba, which has triggered the worst humanitarian disaster on the island in reminiscence. An American oil blockade imposed in January set off a sequence response of day by day blackouts, meals shortages, water shortages, medical emergencies, and reported deaths. “I think it’s intimidation, totally, and we don’t want to be intimidated,” Benjamin mentioned. “We’re telling all the people who went with us don’t be intimidated. Just use this as another spark in the fire to challenge this sadistic policy.”

Code Pink has began to compile the data requested by OFAC, Benjamin added. “We think we didn’t do anything wrong.”

Federal scrutiny of the journey has implications past one group’s mission to Havana. It’s one other blow to Cuba’s already devastated hospitality trade—a serious pillar of the economic system—and represents an extra instrument for turning up strain on the Cuban authorities, in keeping with specialists in journey to Cuba. “This will certainly serve to chill travel to Cuba by well-meaning Americans who have every right under the current structures and categories to go to Cuba,” mentioned Peter Kornbluh, co-author of Back Channel to Cuba: The Hidden History of Negotiations between Washington and Havana, who has led excursions to the island. “But it also is a warning to anybody that opposes the cruel and anti-humanitarian nature” of the present strategy to Cuba. “The Trump administration is weaponizing a humanitarian trip to Cuba to persecute, not just to prosecute, those who are speaking out against the cruel and malicious US policy and trying to help the Cuban people.”

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The Treasure Department’s press workplace didn’t reply to e-mails looking for remark for this story. The existence of the inquiry was beforehand reported by Fox News Digital, which additionally mentioned others acquired a “subpoena,” together with left wing influencer Hasan Piker who traveled to Havana on the Code Pink constitution. As of final week, “your boy has yet to receive a subpoena,” Piker advised his viewers on Twitch.

Official inquiries into American vacationers’ actions in Cuba weren’t unusual within the Nineteen Nineties and early 2000s. However, since President Barack Obama sought to thaw relations between the nations and visited Havana himself in 2016, the belongings management workplace has usually left vacationers alone. “Obama basically decided that OFAC should be out of the travel curtailment business,” Kornbluh mentioned.

Even throughout Trump’s first time period, US journey to Cuba continued to soar, reaching a document 638,000 guests in 2018, in keeping with the Cuban authorities, regardless of Trump’s tightening some classes of journey. There had been few, if any, studies of the US authorities demanding the data of vacationers to Cuba throughout Trump’s first time period and President Joe Biden’s time period, mentioned Robert Muse, a Washington, DC, lawyer with lengthy expertise counseling shoppers on OFAC compliance points.

Americans can journey to Cuba for any of 12 authorized reasons, together with “support for the Cuban people,” “humanitarian projects,” and “educational activities.” The Code Pink group traveled underneath the class of assist for the Cuban individuals, Benjamin mentioned. That means having a schedule of actions that yield significant interplay with the Cuban individuals, in keeping with the laws. Some members of the group spent all their time portray a mural with Cuban artists, as reported by The Nation from Havana, whereas others participated in a day by day schedule of actions posted of their lodge, together with visiting neighborhoods to fulfill residents, listening to audio system, and making artwork with youngsters in a playground.

The March humanitarian help convoy got here underneath withering assault in right-wing information accounts and social media, with headlines like “The Flotilla of Shamelessness in Cuba.” The commentators highlighted a gathering of a whole bunch of convoy individuals one afternoon within the Havana conference middle, the place Cuban President Miguel Díaz-Canel addressed the guests: “Your presence on the island constitutes a profound demonstration of friendship, sensibility, and human commitment to the Cuban people.” The current Fox News report on the OFAC inquiry claims it’s a part of a “broader dragnet…of anti-US Marxists, communists and socialists.”

Demands for data just like the one to Code Pink “go through cyclical periods depending on US-Cuba relations generally, and we’re clearly in a downdraft here,” mentioned Muse. The winds began to alter once more in June 2025 when Trump issued a national security memorandum that, partially, instructed the Treasury to make sure that vacationers adjust to laws and hold data of their actions for 5 years. Indeed, individuals within the convoy confronted prolonged questioning once they landed in Miami on their return from Havana in March. At least 18 vacationers had their digital gadgets searched, and a few telephones and laptops had been confiscated for a number of days.

The most civil penalty for, say, partaking in tourism, which is forbidden, somewhat than permitted actions is $111,000, whereas the prison most is $250,000 and as much as 20 years in jail—although attorneys say precise sentences would doubtless be far decrease.

Muse is targeted on whether or not escalating aggressive enforcement towards vacationers seems to be the most recent screw that Trump has discovered to tighten on Cuba, together with the oil embargo, the current indictment of Raúl Castro, threats of navy motion on the island, and the marketing campaign towards Cuban medical doctors serving in different nations. “If they do an across-the-board set of administrative proceedings, maybe go criminal in a case or two, then they’re fitting it into maximum pressure,” mentioned Muse. “Rights of US citizens then become implicated. This then extends the embargo beyond Cuba and brings it home in aggressive examination of broadly First Amendment–protected activity.”

Benjamin vowed that the scrutiny of the journey wouldn’t deter activists advocating for a change in Cuba coverage. Last week, Code Pink has been on Capitol Hill advocating for resolutions within the House and the Senate that might drive votes on requiring the Trump administration to win congressional approval to launch navy motion towards Cuba. The federal inquiry “is taking time and energy and money,” she mentioned, “but it’s not going not take us away from the main issue,” which is “Cuba and what they’re suffering.”

David Montgomery

David Montgomery, previously a longtime employees author for the Washington Post, is a contract journalist in Washington.

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