When Obama walks off Air Force One onto the red carpet at Jose Marti airport in Havana Sunday, he'll be taking another big step towards normal relations with the island, and kicking another hole in the wall of isolation that the U.S. spent decades trying to build around Cuba.
"The Cold War has been over for a long time," Obama said, before his historic handshake with Cuban President Raul Castro in Panama last year. "I'm not interested in having battles that, frankly, started before I was born."
Obama will be the first American president to visit Cuba since Calvin Coolidge arrived on a battleship in 1928. (Harry Truman dropped by during a Caribbean cruise 20 years later, but didn't go beyond the U.S. naval base at Guantanamo Bay.)
The president hopes to cement the new U.S. policy of engagement with Cuba that he first announced 15 months ago.
"We very much want to make the process of normalization irreversible," said Deputy National Security Advisor Ben Rhodes, who played a key role in secret talks that led up to the opening.
During his two-day trip to Cuba, the president will meet with Castro as well as Cuban dissidents. He'll deliver a televised address to the Cuban people. And he'll take in an exhibition baseball game between the Cuban national team and the Tampa Bay Rays. First Lady Michelle Obama is joining her husband on the trip, along with their daughters, Sasha and Malia.
"Let's not forget that the Castro regime has been guilty of countless human rights abuses," House Speaker Paul Ryan said Thursday. "Unfortunately, it is doubtful that the president will bring up the need for reform during his visit."
The White House says Obama will raise the issue of human rights when he meets with Castro on Monday. He'll also hold a separate meeting Tuesday with human rights activists and others who are critical of the Castro government.
"We know that change won't come to Cuba overnight," National Security Advisor Susan Rice said. "But the old approach — trying to isolate Cuba for more than 50 years — clearly didn't work. We believe that engagement — including greater trade, travel, and ties between Americans and Cubans — is the best way to help create opportunity and spur progress for the Cuban people."
Several dozen members of Congress — both Democrats and Republicans — are expected to join the president's delegation. Business people will also be tagging along in hopes of uncovering new economic opportunities.
While the U.S. embargo against Cuba remains in effect, the administration has been chipping away it over the last 15 months. The Commerce and Treasury Departments have steadily eased restrictions on travel and trade with Cuba. On Tuesday, the administration opened the door for individual Americans to travel to Cuba for "people-to-people" purposes, without having to sign up for an expensive group tour. Direct mail service between the U.S. and Cuba resumed this past week. And U.S. airlines are expected to launch scheduled service to the island later this year, with up to 110 flights a day.
The diplomatic thaw has prompted a surge in U.S. visits to Cuba, located just 90 miles off the southern tip of Florida.
So far, the U.S. overtures have prompted only a limited response from the Cuban government, both economically and politically. American companies, given a green light by Washington to do business in Cuba, still encounter red tape in Havana. And Cuban dissidents still face repression from the authoritarian Castro regime.
Outside experts say while Cuba has made some positive moves, they've been small, and it's not clear when — or even if — more progress will be achieved.
"The great problem, as we know, is a journey of a thousand miles starts with a few steps," said Peter Hakim of the Inter-American Dialogue think tank. "But so does a journey of a only few steps."
Some critics argue Obama should have waited to visit Cuba until the country moves further down the path of reform. But Rhodes disagrees.
"Given the choice between going in December when, frankly, it would just kind of be a vacation down to Cuba, or going now and trying to get some business done, we believe that the time is right," Rhodes said.
The president's outreach to Cuba has also been welcomed by other leaders in the hemisphere, with whom the previous policy of trying to isolate Cuba had been a liability.