ANDREWS AIR FORCE BASE

President Barack Obama flew out of the United States on Sunday bound for a historic three-day visit to the communist-ruled island of Cuba, said an AFP photographer traveling with him.

Crowds gathered and snapped pictures as Obama departed Andrews Air Force Base, just outside the capital Washington, shortly after 1730 GMT for a flight time of a little less than three hours, reversing generations of US attempts to cut Cuba from the outside world.

A light drizzle came down as the president and his family, including First Lady Michelle and the couple's two daughters boarded Air Force One, in a closely watched trip that Washington and Havana hope will seal the renewal of ties after a half-century-long Cold War. Obama, seeking to leave a significant foreign policy mark in his final year in office, was due to see old town Havana late Sunday, hold talks with Cuban President Raul Castro on Monday, and attend a baseball game before leaving Tuesday.

It is the first visit to Cuba by a sitting US president since Fidel Castro's guerrillas overthrew the US-backed government of Fulgencio Batista in 1959 and the first since President Calvin Coolidge's trip to the island 88 years ago.

It won't just be the first visit by a 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 came 88 years ago.

Obama, seeking to leave a historic foreign policy mark in his final year in office, was due to see 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. Havana's old town was crawling with painters sprucing up the picturesque neighborhood. The Stars and Stripes - so long the enemy flag - fluttered from numerous buildings. Early Sunday cleaners swept the narrow, cobbled streets where Obama was due to stroll later and police, both uniformed and plainclothes, were out in large numbers.

"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."

On the eve of his visit, Obama cracked jokes with one of the communist country's most loved comedians, Panfilo, in a three and a half minute video sketch released online and later broadcast on Cuban television - fortunately, since most Cubans do not have Internet. But less light-hearted matters will overshadow the visit.

Although Obama has already loosened restrictions on US citizens visiting Cuba, the lifting of the decades-old US economic embargo can only be decided by a Republican-dominated Congress that is far less keen on detente with Raul Castro's Cuba.

Republicans and some human rights activists have also criticized Obama for dealing with Castro when so many freedoms in Cuba, ranging from the media to politics and economic entrepreneurship, remain highly curtailed.

Dissidents called on the eve of the visit for Obama to promote "radical change," notably a "stop to repression and use of physical violence against all political and human rights activists."

One banned group, the Ladies in White, said they would attempt to demonstrate after attending Catholic Mass, just hours before Obama was to touch down.

The Castro government has warned Obama that lectures on democracy will be "absolutely off the table." But White House deputy national security adviser Ben Rhodes insists that the subject will be brought up.

Obama will also 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 tried 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." And 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.

In the latest sign of the new dynamics, US group Starwood Hotels & Resorts Worldwide said Saturday it had signed three hotel deals in Cuba, a first for any hospitality company since the revolution of 1959.

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.