“¿Que bola Cuba?” Obama tweeted on landing, using Cuban slang to ask what’s going on.
“Just touched down here, looking forward to meeting and hearing directly from the Cuban people.”
Moments later, a smiling Obama emerged from Air Force One with his wife First Lady Michelle and their two daughters Sasha and Malia, clutching umbrellas to shield themselves from a warm afternoon rain shower.
He was greeted on the tarmac by Cuban Foreign Minister Bruno Rodriguez, before loading into his bulky limousine, nicknamed “the beast.”
Obama is not only the first sitting US president since Fidel Castro’s guerrillas overthrew the US-backed government of Fulgencio Batista in 1959, but the first since President Calvin Coolidge in 1928.
Seeking to leave a historic foreign policy mark in his final year in office, Obama will tour the newly reopened US embassy and old town Havana late Sunday, hold talks with Cuban President Raul Castro on Monday and attend a baseball game before leaving Tuesday.
For Cubans dreaming of escaping isolation and reinvigorating their threadbare economy, the visit has created huge excitement.
“A president of the United States in Cuba arriving in Havana on his Air Force One,” wrote popular Cuban writer Leonardo Padura on the Cafefuerte blog.
“Never in my dreams or nightmares could we have imagined that we’d see such a thing.”
For days, Havana’s old town has been crawling with painters sprucing up the picturesque neighborhood and the Stars and Stripes — long the enemy flag — has appeared over numerous buildings.
Early Sunday, cleaners swept the narrow, cobbled streets where Obama was due to stroll later and police, especially plainclothes, were out in large numbers.
But minutes before Obama took off for Cuba, police in Havana arrested dozens of people from a banned group demanding greater human rights, AFP reporters said.
The protesters were from the Ladies in White, formed by wives of former political prisoners. Police bundled them into vehicles outside a church where they attempt to hold protests almost every Sunday.
Republicans and some human rights activists have criticized Obama for dealing with Castro, given the lack of political, media and economic freedom in a country where the Communist Party retains tight control.
Dissidents called for “radical change” on the eve of the visit, but the Castro government warned that lectures on democracy would be “absolutely off the table.”
White House deputy national security adviser Ben Rhodes insists that the subject will be brought up. Obama will meet members of Cuba’s beleaguered opposition and on Tuesday will give a speech at the National Theater carried live on Cuban television.
The United States spent decades trying to topple Cuba’s communist government.
Washington attempted economic strangulation, the failed 1961 Bay of Pigs invasion, and CIA assassination plots against Fidel Castro — including the legendary, but unproven story of sending him an exploding cigar.
Now, after so many failures, Obama has bet that soft power will achieve what muscle could not. The aim, Rhodes said, is to make “the process of normalization irreversible.”
Although a decades-long US economic embargo remains in place — and can only be removed by the Republican-controlled Congress — large cracks in the sanctions regime are appearing.
Obama hopes that a host of incremental and seemingly technical steps will open Cuba’s economy, transforming the island economically and politically, backers of the policy say.
Lawmakers including House Minority Leader Nancy Pelosi were with Obama, while a delegation of political and business leaders was traveling separately.
“It’s a soft war using visitors as the soldiers, commercial airlines as the air force, and cruise ships as the navy,” said John Kavulich, president of the US-Cuba Trade and Economic Council.
In the latest such move, the US government gave the home rental platform Airbnb a green light to accept bookings in Cuba from non-American customers.
Earlier, US group Starwood Hotels & Resorts Worldwide said it had signed three hotel deals in Cuba, a first for any hospitality company since the revolution of 1959.
Cuba’s regime, which for decades defined itself as the people’s bulwark against the Yankee enemy, has bowed to the fact that Cubans would rather do business than make war.
And as if Obama’s arrival were not enough to illustrate the sea change in Cuba, the Rolling Stones — a symbol of the cultural imperialism that communist leaders raged against — are playing a free concert in Havana on Friday.