The pace and timing of rapprochement has already prompted concerns about a superficial transition.
President Barack Obama has called his trip to Cuba a “historic opportunity” in his first comments after becoming the first serving US leader to visit the state in almost nine decades.
Obama arrived in Havana on Sunday evening with his wife and daughters and is due to meet Cuban President Raul Castro later on Monday.
“It’s been nearly 90 years since a US president set foot in Cuba. It is wonderful to be here…for the first time ever Air Force One has landed in Cuba,” he said during a speech at the US embassy in Havana shortly after his arrival.
“This is a historic visit and it’s a historic opportunity to engage directly with the Cuban people and to forge new agreements, commercial deals, to build new ties between our two peoples.”
Excitement in Havana
Al Jazeera’s Lucia Newman, reporting from Havana, said the visit had excited Cubans, many hopeful of what the newly re-established ties could bring.
“Many Cubans were actually saying they needed to pinch themselves, that they could not really believe that an American president was finally coming to their country,” she said.
“People want to know what the president is going to say…he will be addressing the Cuban people on Tuesday [and] this message will be broadcast live on Cuban television.”
Obama is set to meet Cuban dissidents during his visit, a move our correspondent Newman said would have been considered “intolerable” by the government in the past.
“The Cuban government is clearly not happy about it and to make the point, as the president’s plane was coming here, some 50 dissidents were actually arrested.”
Cold War rivalry
The two countries have moved towards normalising relations after a breakdown following the 1959 communist revolution led by former Cuban President Fidel Castro.
Successive US government have tried to oust the Cuban leadership, most notably during the CIA-backed Bay of Pigs invasion of 1961.
Former US President John F Kennedy imposed a trade embargo on Havana in 1962 and in the same year the movement of nuclear missiles from the Soviet Union to Cuba brought the countries close to nuclear war.
Since the restoration of diplomatic relations, the states have signed telecommunication deals and put into place airline services but obstacles remain, including the continuing embargo.
Obama faces opposition to the rapprochement from the opposition Republican party, which controls both Congress and the Senate.
Republican presidential candidate Ted Cruz, who is of Cuban descent, criticised Obama in an article posted on Politico.
“I have news, Mr President: No progress has taken place. Cuba is going backward,” Cruz wrote.