In a speech in Miami's Little Havana enclave, Trump said Cuban rulers were profiting from better relations with Washington but that ordinary Cuban citizens continued to be repressed.
Trump said he was “completely canceling” the “terrible and misguided deal” that
"We will not be silent in the face of Communist oppression any longer," Trump said. "Effective immediately, I am canceling the last administration's completely one-sided deal with Cuba."
Cuba's leaders on Friday night criticized Trump's "hostile rhetoric" and said his announcement signaled a return to "the coercive methods of the past."
In a letter signed by Cuba's revolutionary government and published in Granma, the ruling party's official mouthpiece, the leaders said that Trump's actions "contradict the majority support of American public opinion." It suggested Trump was influenced not by overall opinion polls but by the views of a minority of Cuban Americans who opposed Obama's moves to improve relations with Cuba.
Despite their obvious anger at Trump's attacks, the Cuban leaders did not threaten retaliatory measures. They said they would be willing to continue negotiating with the U.S., so long as it was via "respectful dialogue."
The actual order Trump signed, however, was considerably more modest than the president's sweeping rhetoric might suggest. His directive left key elements of Obama's overtures open: He did not close the U.S. embassy in Havana, nor did he completely block commerce.
In addition, the new restrictions will not take place immediately and are not expected to force businesses to unwind existing deals, an administration official, speaking on condition of anonymity, told reporters in a briefing Thursday.
John Kavulich, director of the Cuba Trade Organization, which tracks business with the island, said businesses will have 90 days to make deals before the American government shuts down.
"The starter pistol has been fired," he said.
Despite those limitations, the new restrictions drew objections from the U.S. Chamber of Commerce, which said in a statement that Trump's moves "actually limit the possibility for positive change on the island."
The main goal of the new regulations is to keep keep money out of the hands of Cuba's military and intelligence services and "empower the Cuban people," a White House official said.
The new rules include prohibitions on Americans spending money on businesses controlled by the military, which has a wide reach in the Cuban economy. That change would affect some proposed hotel projects in which Cuban entities controlled by the military would be partners.
In addition, rules on American travel to Cuba will be tightened, limiting casual tourism. But airlines will continue to be able to fly to Havana, and cruise ships will still dock at the island's ports.
Trump's speech, before an audience that included aging veterans of the 1961 Bay of Pigs invasion — an effort by CIA-backed Cuban exiles to overthrow Fidel Castro's government — was heavy with Cold War rhetoric and references to images, such as gunshots in the ocean breeze, that no longer exist in Cuba.
It amounted to an effort to partially return to the status quo from before December 2014, when President Obama and Cuban President Raul Castro announced they were reopening diplomatic ties after a half-century of hostility.
Soon, Americans could travel to Cuba and businesses, including the tourism industry and food-producing farm states, were involved in commercial deals.
But conservative members of Congress, especially those based here in south Florida, objected, saying that it was mostly the Communist government and Cuban military who were benefiting. Until Cuba's human rights situation improved, they argued, deals with Cuba should be limited.
Florida's Republican Sen. Marco Rubio had lobbied Trump intensely to stick with his campaign pledge to roll back the opening to Cuba.
The timing and location of Trump's announcement raised some eyebrows. He came to Miami as his vice president and three Cabinet secretaries were hosting leaders of Mexico and Central America in a two-day conference on immigration and regional prosperity.
All of the visiting Latin Americans were among the hemisphere's leaders who welcomed Obama's decision to recognize Havana. Until then, the United States was the only country in the world that continued to maintain a hostile position toward Cuba, and Obama's decision to reverse that gained enormous good will for the United States throughout the Western Hemisphere.
Trump's announcement is all but certain to anger Latin America and erode U.S. ability in the region, including Washington's efforts to pressure Venezuela's abusive, leftist government.
"The optics are not the best," said a senior international Latin American finance official in Miami for the conference. Like many diplomats, he spoke on condition of anonymity to talk about the Trump administration.
"The entire region welcomed the United States' normalization of relations with Cuba," said Cynthia Arnson, director of the Latin America program at the nonpartisan Wilson Center think tank in Washington. The hardening of policy "can only add to the growing distance between Washington and the region's democracies."
National Security Council spokesman Michael Anton denied that the timing was aimed at Latin American leaders.
"There's nothing intentional about the timing. It's not a slap in the face," he told reporters on Air Force One as Trump flew to Miami.
"We hope we can get support from other Latin American leaders for this policy," Anton said. "This is a policy that favors the Cuban people over and against an oppressive regime."
But even among Cuban Americans here, some were dismayed.
Arsencio Acevedo, a Cuban who has lived in Miami for nearly 30 years, was critical of Trump's gesture.
"We need communication," Acevedo, 48, who works as a waiter, said. "It is communication that helps us all connect. Cut that off, and you cut off everything."
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6:20 p.m.: This story was updated with a statement from the Cuban government.