But beginning in late 2014, President Barack Obama and Cuban President Raul Castro began a process that gradually thawed diplomatic tensions and eased commercial and travel restrictions between the two countries.
Trump was knocked Friday, though, from both sides.
Obama announced in December 2014 that he and Cuban leader Raul Castro were restoring diplomatic ties between their countries, arguing that a new approach was needed because the policy the US had pursued for decades had failed to democratize the island.
Critics said the changes would only hurt everyday Cubans who work in the private sector and depend on American visitors to help provide for their families.
Declaring Obama's pact with Castro a "completely one-sided deal", Trump said he was canceling it.
"They are cosmetic changes that don't mean anything", he said in Spanish. "He's in Tampa, painting houses, and the more open things are between the USA and Cuba, the better".
"Last month, the Cuban government said it would legalise small- and medium-sized private businesses, we don't know exactly what that will entail right now, but that could significantly expand private enterprise and is a decision they probably made in anticipation for Trump". We do not want U.S. dollars to prop up a military monopoly that exploits and abuses the citizens of Cuba.
Among the companies that jumped in to Cuba was San Francisco-based Airbnb, who said a year ago that Cuba was its fastest growing market. Today, the city 30 miles west of Havana is home to the county's main cargo facility, where freighters unload containers of supplies for the country's booming tourism industry.
This should shield US airlines and cruise lines now serving the island.
Although the speech didn't include many details on the specific policy, it was critical of the Obama administration's policy. He says he remains focused on finding ways to "increase trade with Cuba rather than cut off relationships that have the potential to create new jobs, bring in revenue and boost our national economy". Groups can organize "people to people" trips, but the program must be full-time and educational, and activities must enhance "meaningful" contact with the Cuban people, "support civil society in Cuba, or promote the Cuban people's independence from Cuban authorities".
Obama's new policy of engagement unleashed a flood of American visitors, pumping cash into Cuba's nascent private sector, even as the centrally planned economy hit its first recession in almost a quarter century.
GAESA operates dozens of hotels, tour buses, restaurants and other facilities.
Trump's vow to keep the broader decades-old USA economic embargo on Cuba firmly in place drew criticism from some US farmers, especially growers of corn, soybeans and rice.
President Donald Trump's broad overhaul of United States policy toward Cuba will not restrict scheduled airline flights, but will see the U.S. government crackdown on existing travel regulations.
"We do not want USA dollars being used to prop up a military monopoly that exploits and abuses the citizens of Cuba", Trump said.
Yet it also exposed the shortcomings in Obama's approach. Obama and his aides argued that commerce and travel between the countries, which has blossomed since he relaxed the rules, would make his policy irreversible. "Rubio and his wife, who was, by the way, lovely, and we had a very good discussion about Cuba because we have very similar views on Cuba", Trump said, adding that "Cuban people" were "very good" to him in the 2016 election.