Administration officials who briefed the press on the details of the trip said they view it as an opportunity to make the normalization of diplomatic relations with the communist nation "irreversible" in the face of criticism from Republicans, who have pressed to keep an economic embargo against Cuba on the books.
The three-day trip to Cuba, which will be followed by a trip to Argentina, will include a bilateral meeting between Obama and Cuban President Raul Castro.
Deputy National Security Adviser Ben Rhodes, who has been deeply involved in the administration's Cuba policy shift, said Obama is looking forward to a frank discussion with Castro about ways the two nations can work together, but also about what differences remain after decades of isolation.
Rhodes said the president will be "very candid about areas of disagreement, including the human rights practices that have concerned us in Cuba and our support for universal values in Cuba and around the world."
The entire first family, including first lady Michelle Obama, daughters Sasha and Malia, and the president's mother-in-law, Marian Robinson, will accompany the president on the trip, along with a large delegation of Cuban-Americans, some of whom have expressed skepticism about re-establishing ties with the communist dictatorship.
Rhodes said Obama will also deliver a speech "to the Cuban people" that will be broadcast on state-run television Monday. Prior to delivering the speech, Obama will meet with members of Cuba's civil society -- a meeting that will include prominent political dissidents and human rights activists, some of whom have been jailed by the Castro regime in the past for speaking out.
Monday night, the Obamas will be the guests of honor at a state dinner hosted by Castro at the Presidential Palace in Havana.
And before departing on Tuesday, Obama will share in one of the closest cultural ties between Cubans and Americans -- a baseball game. Major League Baseball's Tampa Bay Rays will play an exhibition game against the Cuban National Team in Havana, which the president and his family will attend.
Baseball is, of course, known as America's "national pastime" but in Cuba it is a national obsession. Rhodes pointed out baseball is a prime example of ways normalizing relations can improve cultural understanding, while also promoting commercial ties.
Where Cubans once resented American baseball because so many of the nation's best players defected to play here, now, Major League Baseball is hoping to establish official ties with Cuban development teams and new rules proposed by the administration would allow Cuban ballplayers to sign contracts without renouncing their Cuban citizenship. Presently, the American rules state a player has to defect to the United States before he can sign a contract and be paid by a U.S. team.
"Baseball is obviously something that the United States and the Cuban people share a common love of and it's a part of both of our heritages, and frankly, also part of the type of exchanges that we are pursuing in business, in culture, in the arts, in sports that can bring the American and Cuban people closer together," Rhodes said.