The billionaire businessman, who was pictured in front of torn-down buildings and uprooted trees, said he knew the people of the British Virgin Islands would "bounce back stronger than ever".
Hurricane Irma was one for the record books in Cuba.
As of Sunday, officials said 27 people died from Irma-related incidents in the Caribbean region, including three deaths reported in the USA islands of St. Thomas and St. John.
Rain and seawater flooded towns and cities, including the colonial center of Havana, the country's capital and a key tourist magnet.
"This story is about the tens of thousands of people who have lost their homes and their livelihoods".
By Sunday morning, the U.S. National Guard evacuated by aircraft some 500 of the more than 5,000 American citizens who were on St. Martin when the storm struck.
By Saturday evening, the sea had penetrated two blocks over parts of the city's historic seafront boulevard, and the waters were expected to advance farther as the surge grew. Flooding continued Sunday afternoon along the malecón, spreading into adjacent streets with waist-level water in some areas. Elsewhere in the Caribbean, 24 deaths have been attributed to Irma.
British visitor Josephine Breslin, 49, spent the night on an inflatable bed in a hotel bathroom when Irma's 120 miles per hour (195 km) winds walloped Cuba's top beach destination, but after helping sweep up on Sunday morning, she felt ready to start relaxing. It was Cuba's worst hurricane death toll since 16 died in Hurricane Dennis in 2005.
As Cubans tried to dry out from the effects of Hurricane Irma, the government said restoring the electric grid, dealing with water shortages and resuming the school year were its main priorities.
State television reported severe damage to hotels on the northern cays off Ciego de Avila and Camaguey provinces.
Hurricane Irma freed as many as 100 prisoners in the British Virgin Islands, who are now believed to be running through the territory, a top United Kingdom official said Tuesday.
Laura Cockford, whose mother had been visiting St. John at the time of the storm, put the matter plainly on Friday: "The island is destroyed". Many residents there have been evacuated ahead of Jose.
Dutch King Willem-Alexander flew to St. Maarten, which shares the island with the French dependency of St. Martin, to see the devastation wreaked by Irma and express gratitude to relief workers.
Meanwhile, the State Department continues to coordinate evacuation efforts for US citizens who remain on St. Martin, through social media, radio and in reaching out to hotels and Airbnb locations, a spokesperson Heather Nauert said in a statement.
French President Emmanuel Macron was scheduled to arrive in St. Martin on Tuesday to bring aid and fend off criticism that he didn't do enough to respond to the storm.
"I will try my best, but I have nowhere to spend the night", she said, adding that the homes of her family and friends are already full. "That's the problem, everyone has their own problems at the moment", Cluff said.