Mrs. Obama will meanwhile on Monday meet with female Cuban students, some of whom have studied in the U.S., the White House says, as part of her Let Girls Learn initiative.
That president and first lady will participate in a State dinner hosted by the Cuban government at the Palace of the Revolution.
The following morning the president will give a speech, in which he will 'review the complicated history' between the countries, the White House says, 'but also to look forward to the future, and to lay out his vision for how the United States and Cuban can work together, to how the Cuban people can continue to pursue a better life.'
Afterward he will meet with political dissidents before attending an exhibition game between the Tampa Bay Rays and Cuban National Team.
'Americans and Cubans share a love of baseball, and this is yet another powerful reminder of the kinship between our peoples, as well as the progress we can achieve when we leverage those natural ties,' the White House's chief spokesman, Earnest, said Friday.
Obama's meeting with opponents of the Cuban government has been especially kept under wraps going into the trip.
Earnest was unable to say today who the president will meet with specifically while he's there while promising press a list at a later time and access when it happens.
White House Press Secretary Josh Earnest said today that he had not seen the list but provided assurances that it had not been dictated by the Cuban government.
'The list of people invited to meet with the president in Cuba is non-negotiable,' he told reporters. 'I would not be surprised if there might be people on that list that the Cuban government would prefer that we not meet with...and I don't know whether or not they've raised those concerns or not.
'But I can tell you that the President is going to move forward and host meetings, and have a conversation about human rights with the people that he chooses to meet with,' Earnest said,
As observers have noted, it would be difficult for the president to meet with imprisoned dissidents without working with the Cuban government, though.
Not having reviewed the list, Earnest said he was unable to vouch for the status of the participants, 'but we certainly are expecting the President to have the opportunity to meet with everybody who is invited and chooses to come.'
The Cuban Observatory on Human Rights last month said the number of dissident arrests had went up - not down - since the U.S. and Cuba announced on Dec. 17, 2014 that they would resume high-level diplomatic relations.
In January alone, 1,474 people were 'arbitrarily' detained, the human rights organization told Bloomberg Politics.
This week Cuba released seven dissidents and allowed them one trip abroad on the condition that when they return they will serve the remainder of their sentences out of prison and be banned from additional foreign travel.
'It appears to be some kind of gift they want to present to Obama, but in reality it is nothing concrete because when we come back we will return to legal limbo,' Martha Beatriz Roque, one of the prisoners, told Retuers.
Responding to criticisms of Obama's trip on Friday, his spokesman said, 'I would acknowledge that there are places where we haven't seen nearly as much improvement as we would like, but there have been some places where we have started to see improvement in Cuba, and we certainly are going to go and press on those changes.'
And he said of Obama's meeting with the dissidents, 'I think the symbolism of the President sitting down with them in their home country and showing support for their cause will be a really powerful thing I think both in real terms but symbolically as well.'
Obama is the only U.S. president aside from Calvin Coolidge to visit Cuba while in office. He and Castro had a formal meeting last April at the Summit of the Americas Conference but that was in Panama.
The visit to Cuba by Obama follows an agreement between the countries more than a year ago to begin normalizing relations, and 'it signals a new beginning' between the two countries, acting U.S. Ambassador to Cuba Jeffrey DeLaurentis told reporters Wednesday.
The Cuban government says that cannot happen until a U.S. embargo banning trade and tourism is lifted on the country and the foreign government returns Guantanamo Bay. U.S. officials have steadfastly said it cannot have the land occupied by naval base and prison back.