The daredevil climber nicknamed "Spider-Man" is famous for scaling some of the world's tallest skyscrapers without a safety line.
Now Alain Robert has his sights set on a slightly less imposing edifice that nonetheless offers its own challenges - and plenty of symbolism.
The 50-year-old Frenchman is in Havana on a mission to conquer the 27-story former Hilton Hotel that was taken over after the 1959 Cuban Revolution and redubbed the "Habana Libre", or "Free Havana". Fidel Castro briefly set up his personal offices there after his triumphant march into the capital.
"This hotel has great meaning for me. It's impressive not for its height, which is not great, but because it's a building that symbolises the Cuban Revolution," Robert said. "I consider this hotel to have been a challenge for Castro and I love the idea that now it's my turn to attempt the challenge."
At 413ft, a fall from the Habana Libre would still be deadly. But the building is dwarfed by other giants Robert has climbed unaided - Chicago's Willis (nee Sears) Tower, New York's Empire State Building, Taiwan's Taipei 101 and Malaysia's Petronas Towers - all of which were the tallest in the world at some point. "This is a different type of building with a unique structure, a little deteriorated in some places," Robert said. "That's the challenge for me, because really it's not very tall."
Robert has been sizing up the hotel in recent days and securing permission from island authorities for the climb. He has gained permission and and intends to make the attempt on Monday.
On Friday, clad in green leather trousers and a black leather jacket, he scouted out his rooftop destination and posed for photos with hotel workers.
Robert said he has been drawn to trees and buildings since childhood. Locked out of home one day at the age of eight, the budding "Spider-Boy" climbed seven stories to his parents' apartment rather than wait in the street. "Height fascinates me. I love the purity of the vertical. I'm drawn to this game between life and death. In those moments I feel fulfilled," he said.
The climbing life has had its ups and downs, he acknowledged. At 20, a 49ft fall broke multiple bones and put him in a coma for six days. Since then, Robert says he suffers from bouts of vertigo and French social security officials consider him disabled.
But he defied doctors' predictions that his climbing career was over and has gone on to scale ever-loftier heights. Two years ago he took six hours to summit what currently is the world's tallest building, the 2,717ft Burj Khalifa in Dubai, but used safety equipment. "I am afraid, of course, I am a human being like any other. But it doesn't stop me from doing what I love," Robert said. "I conquer the fear."