One night not long ago, in a new restaurant in Havana called VIPs, the owner, a white-haired Catalan named Jordi, was speculating about what life might be like in Cuba after a reconciliation with the United States. “Come, let me show you,” he said confidingly, leading the way to a large outdoor space between the neighboring building and his own, an eighteenth-century villa built for a Spanish marqués. Gesturing with his hands, Jordi indicated where he was building an open-air bar and eatery, a wine cellar, a “chill-out area.” “It will be a club for friends,” Jordi said. “Friends with money.”

Inside, Hugo Cancio, one of Jordi’s friends in the new transnational élite, sat at a corner table. A Cuban-American businessman, Cancio lives in Miami but shuttles to Havana so often that the VIPs menu has named his favorite dish for him: the Don Hugo Paella. Cancio is fifty-one, tall, with an athlete’s shoulders and a limber gait. He was accompanied by his daughter Christy, who had recently finished college in the U.S. Their table looked out on a square bar, a dozen tables full of smartly dressed people, and a huge screen, with Chaplin’s “Modern Times” on a continuous loop. On his iPhone 6, Cancio showed me a selfie that he and Christy had taken earlier that day with Conan O’Brien, who was in Havana taping his show. O’Brien had invited them to join him at El Aljibe, an open-air restaurant that is popular with diplomats and Cuba’s senior nomenclatura. “What do you think?” Cancio asked me, smiling. “Cuba’s changing, man.”

Last December, after five decades of Cold War enmity and eighteen months of secret talks, the United States and Cuba announced that they had agreed to normalize relations. It was a rapprochement so long in coming that younger generations, without much memory of invasions, embargoes, and the threat of nuclear obliteration, barely knew why the bad feeling was so ingrained in the politics of both countries. Cancio is a casualty, like many others, of all that preceded this tentative settlement. He left Cuba in the Mariel boatlift of 1980, in which as many as a hundred and twenty thousand Cubans made a traumatic exodus to the United States. Thirty-five years later, as the C.E.O. of a holding company called Fuego Enterprises, he moves freely between Cuba and the U.S. After spending years cultivating connections in both countries, he has become an intermediary sought after by the increasing numbers of Americans—investors, politicians, celebrities—who are going to Cuba. He is pleased to tell you about his private meeting with Sting, or with Paris Hilton. When Google visited Havana recently, a delegation came to his office to discuss the local situation. In February, Cancio spoke to a gathering of political conservatives in Washington, D.C., and in April he addressed an audience in New York at a conference about Cuba organized by the Wharton School of Business.

Cancio is recognizably Cuban, but he is also a man of earnest American discipline. He meditates and does a hundred pushups each morning. His bedtime reading lately is Hillary Clinton’s “Hard Choices” and a volume by Deepak Chopra. In 2012, he launched OnCuba, a bimonthly magazine stocked with ads, profiles of artists and musicians, and articles on tourist destinations. In the past year, he has added a quarterly art magazine, aimed at collectors and investors, and a real-estate supplement. Cancio has ambitious plans to expand Fuego Enterprises. In 2010, after Raúl Castro announced sweeping reforms to open up the island’s economy, allowing more Cubans to own their own businesses—known as cuentapropismo—and to buy and sell property, Cancio assembled a team to assess investment possibilities. He and his partners decided to focus on media and entertainment, and then move into real estate, tourism, and telecommunications. “Our goal was to position ourselves quickly, so when the market opened we would be among the first to be established,” he said.

For now, Fuego is distinguished more by its potential than by its assets. “If you look at the financials of the company, it’s a very speculative investment and not a lot to get excited about,” Thomas Herzfeld, who manages the Herzfeld Caribbean Basin Fund, one of Fuego’s largest investors, said. “But if you look at Hugo there’s everything to get excited about. He’s a leading expert on Cuba, he’s well respected there, he cares about Cuba and its people.”

Cancio told me that it will likely take three to five years to see real change in Cuba. In the meantime, the island, like any other country undergoing a radical transformation, is a confounding place to do business. In recent decades, businesses from Europe and Canada have invested in Cuba, with uneven results; many deals dissolve, with investors disappointed by returns or frustrated by the exigencies of working with Castro’s government. In a few cases, foreign businessmen have been abruptly jailed, on vague charges of corruption, and their businesses seized. Cancio’s partner Ariel Machado, also a Cuban, jokes about nightmares in which a shadowy rival reaches out to chop off his hand with a machete.

Cancio puts a sunny face on all this complexity. He claims that he “loves uncertainty,” and has faith in the leadership of both countries: “I admire President Obama. And I’ve always admired Fidel Castro. I use him as an example when I am invaded by discouragement—which doesn’t happen much—because this is a man who had an idea and persuaded eighty other people to face an army of fifty thousand, and to cross an ocean to do it. So when people told me you can’t open a media space in Cuba I say, well, Fidel did his revolution.”

To a visitor, Havana appears much the same as it has for decades––people at loose ends, distressed buildings—but there has been an explosion of small private enterprises and, with them, pockets of encouraging prosperity. For the first time since the sixties, when Castro declared a “revolutionary offensive” to “eliminate all manifestations of private trade,” Cubans are being allowed to take charge of their material lives. People are better dressed; there are more cars on the road; and everywhere there are new restaurants and bars and hostels, where Cubans rent rooms to foreign visitors. In early April, Airbnb announced the launch of Cuban operations; by month’s end, Governor Andrew Cuomo had flown in with a planeload of New York business executives for a trade summit, and an N.B.A. good-will delegation had set up training camps for Cuban athletes. On May 5th, the U.S. Treasury Department lifted restrictions on ferry services from Florida; the same day, Jet Blue said that it planned to begin flying between Havana and New York.

Tourism has surged nearly twenty per cent this year, and hotel lobbies in Havana are noisy with troubadours singing “Guantanamera” and odes to Che Guevara; buses and luridly painted old Chevys trundle sightseers around the city. There are Europeans, Canadians, Brazilians; one morning, I saw a group of elderly Chinese visitors dressed in safari clothing exploring the grounds of La Finca Vigía, Hemingway’s home.

Increasingly, there are also Americans, mostly sixty-somethings on “cultural tours” but also college students and hipsters from New York and Los Angeles. People in Havana joke that the latest accessory for an evening out is an American friend. The city’s harbor is being refurbished to accommodate U.S. cruise ships. Cancio’s new travel arm, OnCuba Travel, offers guided tours to Americans with the slogan “Be the first to witness the rise of free enterprise in Cuba.”