Obama’s whirlwind trip is a crowning moment in his and Cuban president Raul Castro’s ambitious effort to restore normal relations between their countries.
While deep differences persist, the economic and political relationship has changed rapidly in the 15 months since the leaders vowed a new beginning.
Wielding an umbrella on a rainy Havana afternoon, the president stepped off of Air Force One and was greeted by top Cuban officials, including Cuba’s foreign minister and US ambassador.
He was joined by first lady Michelle Obama and daughters Malia and Sasha.
His first stop was to be the new US Embassy in Havana, which was opened amid great fanfare last year.
After greeting embassy staff, Obama and his family were to tour Old Havana by foot, including Havana Cathedral.
For more than 50 years, Cuba was an unimaginable destination for a US president, as well as most American citizens.
The US severed diplomatic relations with Cuba in 1961 after Fidel Castro’s revolution sparked fears of communism spreading to the Western Hemisphere.
Domestic politics in both countries contributed to the continued estrangement well after the Cold War ended.
The last visit to Cuba by a US president came in 1928, when Calvin Coolidge arrived on the island in a battleship.
Obama’s visit was highly anticipated in Cuba, where workers furiously cleaned up the streets in Old Havana and gave buildings a fresh coat of paint.
American flags were raised alongside the Cuban colours in parts of the capital, an improbable image for those who have lived through a half-century of bitterness between the two countries.
Many Cubans were staying home to avoid extensive closures of main boulevards.
By early afternoon the Cuban government did not appear to be calling out crowds of supporters to welcome Obama, as it has with other visiting dignitaries.
The president’s schedule in Cuba is jam-packed, including official meetings with Raul Castro and an event with US and Cuban entrepreneurs.
At Havana Cathedral, Obama was to be greeted by Cardinal Jaime Ortega, who helped facilitate months of secret talks between US and Cuban officials that led to the normalisation of diplomatic relations in December 2014.
A highlight of Obama’s visit comes tomorrow when he joins Castro and a crowd of baseball-crazed Cubans for a game between the beloved national team and Major League Baseball’s Tampa Bay Rays.
The president also planned a speech at the Grand Theatre of Havana laying out his vision for greater freedoms and more economic opportunity in Cuba.
Raul Castro planned to greet him today at the Palace Of The Revolution.
Two years after taking power in 2008, Castro launched economic and social reforms that appear slow-moving to many Cubans and foreigners, but are lasting and widespread within Cuban society.
The changes have allowed hundreds of thousands of people to work in the private sector and have relaxed limits on cellphones, Internet and Cubans’ comfort with discussing their country’s problems in public, for example.
The Cuban government has been unyielding, however, on making changes to its single-party political system and to the strict limits on media, public speech, assembly and dissent.
Obama will spend some time talking with Cuban dissidents.
President Obama arrives in Cuba, becomes the first sitting U.S. president to visit the country in 88 years https://t.co/PEIYSUlhUb— MSNBC (@MSNBC) March 20, 2016