By Karl Vick
March 26, 2015

The wait in the customs line at José Martí International Airport is mostly like the wait at any airport: tedium cut by an irrational but persistent worry that you’ve done something wrong and are about to be found out. It’s a normal apprehension that acquires a special edge in a country it was all but illegal for a U.S. citizen to enter for the past half-century.

But Cuba has suddenly cracked open, and so has the face of the man at the passport counter. He wears a uniform, rubber gloves and a smile–a wicked one, directed not at you but at the co-worker standing behind him, a woman who has placed her own gloved hand on his shoulder in a flagrant act of workplace flirtation. They are laughing. “Welcome,” the man says.

What this means is not clear until I pass through security, which air travelers to Havana encounter upon arrival. “Es necesario,” says the young woman beside the magnetometer, but her words say less than her look. For the duty of guarding the revolution, the uniform worn by the women milling about the arrivals area turns out to be a fitted khaki blouse, a snug skirt and patterned black stockings. What awaits the visitor to Cuba now that President Barack Obama has begun to remove the barriers to the island for Americans? In two words, fishnets and epaulets–the telling juxtaposition of a warm and convivial population clad in the trappings of a conflict almost no one takes seriously anymore.

It was 1989 when the Cold War ended, leaving Cuba to make its own way in the world without the financial support of the communist bloc it had served as proudly defiant bowsprit. A quarter-century later, Washington and Havana finally agreed to acknowledge that things may have changed. Among the visitors on the January day I arrived was a delegation from the U.S. State Department, the most senior in 35 years, on hand to negotiate the reopening of a U.S. embassy in Havana and a Cuban one in Washington. The talks went well, riding the surge of giddy good feeling that greeted the Dec. 17 joint statements by Obama and Cuban President Raúl Castro, who took over seven years ago for his revolutionary brother. Something about the announcement, so out of the blue, made a lot of people in both countries happy. Despite bumps and strains in the months since, Obama and Castro prepare to meet at a hemispheric summit on April 10, with Americans inclined toward Cuba a little like residents of Germany East and West: as once intimate cousins freed to renew acquaintance after a long forced separation.

“I believe in humanity. We think everything can be better, to benefit both countries,” says Caridad Alfonso, sipping a beer after work near the Malecón, the iconic seawall that protects downtown Havana from waves that gain force across 90 miles (145 km) of the Florida Straits. A doctor, Alfonso has met Americans at conventions in the Bahamas; she’d like to know more.

“I don’t have American friends,” says her companion, Leonel Díaz.

“Not yet,” says Alfonso, with a smile. “He will find them.”

Reunited

And what will Americans find? The answer depends partly on what they expect. The vision of Cuba that dominated U.S. foreign policy since 1961 would strike fear into any visitor. “That imprisoned island” is how John F. Kennedy referred to it, after sending lightly armed Cuban exiles to the Bay of Pigs in hopes of deposing the new government led by Fidel Castro. The exiles were routed but came to dominate the U.S. view of Cuba for the next half-century, defining Castro’s regime as totalitarian and the Cuban people as victims.

There was no shortage of facts supporting that view. Castro’s government imprisoned tens of thousands in the name of protecting the revolution that in 1959 ousted the U.S.-backed dictator Fulgencio Batista. Castro’s subsequent embrace of the Soviet Union promptly led to the Cuban missile crisis, the world’s closest brush with nuclear war, triggered by the discovery of Russian missiles west of Havana. But in retrospect, the Cold War only framed what was at heart a neighborhood grudge match. For two more decades, Washington plotted against Castro–most famously in a range of assassination plans that included exploding cigars.

“The revolution is a very complex social phenomenon,” a senior Cuban official tells me one afternoon, speaking fluent English but blanching at the suggestion of being named in print. “The United States acted very badly from the beginning. They pushed us into the arms of the Soviet Union. This was not our plan. But you’re put in the position where you have to survive, and you have to survive.”

In some ways, Cuba more than survived. Perhaps no country so poor–monthly salaries in Cuba average $20, with free rent and food-ration cards–has so much to lose. Some of its assets are in plain sight, set off nicely in the slanting afternoon light that floods Havana’s avenues. The shaded streets, like the vintage American sedans that putter along them, are old but immaculately kept. The literacy rate is 99.8%, and the health system is among the world’s best. Cuba has a lower infant mortality rate than America.

Other achievements involve stark trade-offs. Ordinary Cubans need permission to move and to go into business. If they had access to the Internet–one of Obama’s stated goals–they would expect to be monitored the way they are on the phone, or even chatting on the street. Every block has its Committee for the Defense of the Revolution to inform on the neighbors.

But it’s not only the state that feels secure. In a region plagued by a drug trade and the violence that accompanies it, Cuba is all but free of both. Police here carry neither the guns nor the swagger that remain queasy hallmarks of neighboring societies. The murder rate is one-tenth of Jamaica’s and one-seventh of the Bahamas’; in the western hemisphere, only Canada and Chile rank lower. The magnetometers at the airport begin to make sense. “The good thing about my country is no drugs at all,” says Julio Pérez, 49, a fishing guide. “No guns on the street, because no drugs, no guns. And,” he adds, “really strong culture.”

Which is the other thing people expect from Cuba and will be looking for once cruise ships and airliners from the U.S. begin arriving, perhaps later this year. “I think the long-term appeal will be the culture,” says Carolyn Spencer Brown of CruiseCritic.com. The vision of Cuba that arrived on U.S. shores with The Buena Vista Social Club, the 1997 album Ry Cooder recorded in Havana, frightened no one. Music is a way of life here, the rumba a national institution. Artists do double duty as ambassadors. Cuba has a way of producing pleasures even cold warriors had a hard time letting go. Before signing the order imposing a permanent embargo on Cuba in 1962, Kennedy instructed an aide to buy as many cigars as he could lay his hands on (1,200, it turned out). This is the Cuba that grew only more attractive as the Studebakers lost their compression and the walls of the Old City crumbled in the salt breeze.

“It’s set in its time, at the moment,” says Wendy Hicks, a British tourist visiting the island. “And it’d just be a shame to miss what it is. Because it is unique.” She sat with a friend in a hotel lobby in the heart of Habana Vieja, two tables from a Canadian family playing cards. Canadians–not bound by the embargo–account for more than a third of Cuba’s tourists and have been arriving in even larger numbers lately, in anticipation of an American influx they fear will drive up prices or, worse, simply ruin the place. For Cubans, the U.S. rapprochement clearly raises hope in a very material sense. “Let them bring stuff so we can have stuff” is how Díaz puts it, drinking his beer. But the same opening makes visitors nostalgic in advance, launching into paeans to Old Havana that sound like eulogies. (“We wanted to see it before McDonald’s arrives,” one says.) Such is the delicacy of Cuba’s appeal, or the flatness of so much of international travel.

“For people who’ve been everywhere, it’s the one place you couldn’t go, so I think there’s going to be a lot of curiosity,” says George Hobica, president of AirFareWatchdog.com, which follows U.S. airlines. But the invasion, when it comes, may initially be no more successful than that of Kennedy’s doomed exiles. Cuba has only 60,000 hotel rooms, an inventory wiped out by an international education conference the week after the U.S. delegation departed. There are also thousands of rooms licensed for rental to foreigners in private homes, designated by official signs–but it’s not only the rooms that are spartan. There’s almost no Internet outside major hotels, and a creaking cell network won’t support smartphones. In the Instagram age, such deprivations may qualify as adventure travel. At least for a while. “There’s this tremendous interest. It’s still this idea that Cuba is the forbidden fruit. That’s what is making it exciting,” says Lucy Davies, a Brit who runs a Havana company specializing in bicycle tours. “But it would be a disaster from the Cuban side to open the floodgates. I also don’t think the average American is ready to put up with the discomforts of traveling in Cuba.”

Great Expectations

Change sometimes equals loss. To me, Havana seems much as it did when I visited in 1997, entering through the loophole U.S. law left for journalists. Except on Varadero, the generic resort zone two hours east of Havana, tourists were relatively scarce. We had to hire a government guide, but he left us alone to walk through the old city as life spilled out of the apartments onto the street. At a dominoes table, a cackling old man in shorts marked his victory with hip thrusts toward the ear of the old man he had vanquished. The nearby Plaza de Catedral was an open-air gallery, and artists would come to your hotel with more work. Only three or four restaurants took dollars, a currency so coveted that at one, we discovered that our waiter was in fact a heart surgeon trying to make real money. A local man invited us to his home for a dinner of cut-up hot dogs in rice–a feast in a country where people can go a long time without eating meat; he waited until after the meal to try to sell us black-market cigars.

“It was still very much a living city 17 years ago,” says Davies, who fears for Cuba not the advance of Starbucks but a creeping inauthenticity, already glimpsed in the handful of for-hire vintage (imported before the embargo) cars painted in gaudy citrus hues. The formerly stately El Floridita, birthplace of the daiquiri, has become a tourist trap, complete with a bronze statue of Ernest Hemingway in his preferred corner. And though the hole-in-the-wall bar La Bodeguita del Medio, where Papa drank mojitos, remains true to itself, the art market has been moved to a former train shed. It’s now dominated by mass-produced paintings that reduce Havana to a cartoon–a ’55 Plymouth parked outside La Bodeguita.

It would take an act of Congress to bring in the American fast-food chains the connoisseurs fear; Obama’s changes nibble at the edges of the embargo, which remains the law of the land. But he freed U.S. citizens to book their own travel, as long as they say it’s for cultural enrichment rather than tourism–a watery distinction, especially in Old Havana. There, in a gift shop off the Plaza de Armas, an interview with the owner abruptly stops when a band starts playing in the street, suddenly alive with a parade led by men on stilts. It’s an artificial Day-Glo show meant to please tourists. But at the sound of maracas, what explodes out of the shop is the real thing, an old woman clutching a housedress and a cigarette, rolling her shoulders and winking as she rumbas toward the music. A boy and a dachshund follow, the dog lying down on the sunny cobblestone, where a young tourist bends at the waist to take its picture. “We don’t pay her a salary,” a clerk says, meaning the dog. But a small stipend might be in order. This, after all, is what people come for.

The Pragmatist

Raúl is not fidel. The younger Castro knew Che Guevara, hid in the Sierra Maestra just like his brother and is now 83. But he disdains the limelight, almost never gives interviews and, in Politburo affairs, seeks consensus. President since 2008, he appears content to leave Fidel’s fading slogans–Socialismo o muerte (socialism or death)–embroidering public spaces, except, apparently, where something new is going on. In Mariel, the port city a half-hour west of Havana, bulldozers are creating a massive, free port zone, built with Brazilian money for operation by Singapore. The idea–for foreign companies to set up free of the regulations that normally hamper investment here–is not a terribly socialist one, which is why the towering billboard at the entrance to town reads, “Every step that we take should be accompanied by establishing a climate of order, discipline and excellence. –Raúl.”

“Look, Raúl is a pragmatic fellow,” says Carmelo Mesa-Lago, a University of Pittsburgh economist who has followed Cuba for decades. But pragmatism in the Cuban context goes only so far. Three days after his joint announcement with Obama, Raúl appeared before the National Assembly, pushing back any assumption that rapprochement with Washington amounted to a repudiation of “our ideas.”

Still, something has got to give. The plain fact is, for all its accomplishments (and Cuban doctors were among the first in West Africa when Ebola broke out), the country has always been an economic basket case. Fidel’s famously impulsive economic experiments–a superproducing cow! Coffee plantations ringing Havana!–have been condemned to the sandbox of history, alongside Che’s utopian vision of a “new man” who would work devoid of self-interest. A hero to many for defying the U.S.–especially in Latin America, where the U.S. historically regarded its neighbors’ sovereignty as optional–Cuba has never managed to stand on its own, always maintaining an unhealthy dependence on an outside patron. First there was colonial Spain, then capitalist America (which in the 1950s had a stake in virtually every sector of the economy), then the Soviet Union and, recently, U.S.-bashing Venezuela. The late Venezuelan President Hugo Chávez loved to tweak the U.S. by propping up its regional rival through generous subsidies of oil and cash, but his successor Nicolás Maduro may be forced to slash that aid as depressed crude prices send his country’s economy into free fall–a fact not lost on Raúl. “[Cuba is] in very dire economic straits,” says Mesa. “They need the United States. Venezuela’s economy could collapse, and then what are they going to do?”

What indeed. “We have realized some things,” says the senior Cuban official. “We, before, didn’t all the time appreciate the role of the market. Now we realize we need some market in some places.” But, he adds, “If we decided to turn to capitalism, it will not be U.S. capitalism. We want to be Cubans and try to find our own way to do things, according to our history, according to our culture and so on. We have to find ways to make the life of our people better. The world is not the way you want it to be. The world is the world, and you have to find a way to be in harmony with it.”

It’s not as if a communist country has never transitioned to the global marketplace. But the record is so uneven that Raúl sees it as reason to proceed with utmost caution, even though he has vowed to cede power in 2018. “No shock therapy,” he says.

The result is reform at dead slow. Farmers, for instance, can cultivate some land privately, as in China and Vietnam. But unlike those countries, Cuba requires its farmers to sell much of their harvest to the government, at below-market prices. Even tourism poses threats. The island’s famous social equality can be subtly undermined by glossy private restaurants pitched to foreigners that also draw a few Cubans wealthy enough to dine in style.

Then there are the hard-liners, the Cuban officials who are as opposed to rapprochement with Washington as the Cuban-American exiles still stewing in Miami. “I don’t want to mention names, but some inside the top levels in government still have the siege mentality,” says Carlos Alzugary, a former Cuban diplomat who lectures on relations with the U.S. The old guard makes common cause with Caracas, which Raúl hastened to voice support for after Obama imposed sanctions on seven Venezuelan security officials in March. The flap threatened to delay the embassy reopenings, which the Administration hoped to announce before the April 10 start of the Summit of the Americas in Panama City.

But time, which in Cuba often seems to stand still, does its work. Just as the senescence of the exile community emboldened Obama, a new generation has emerged inside Cuba’s one-party establishment, showcased by the delegation negotiating with the U.S. More than half of the 2 million Cuban Americans in the U.S. were born there. And as regulations have relaxed in recent years, the island’s 11 million residents have come to see the U.S. less as an ideological threat than as a source of money transfers from relatives; Obama’s new rules might allow in $2 billion more, as much as Cuba spends importing food. “For a long time, leaving Cuba for the USA was becoming a CIA agent,” says Alzugary. “No more.”

Will engaging Cuba change how it’s governed? That’s far less certain. The example of China, another country that remains communist in name, demonstrates that economic reform doesn’t automatically mean political freedom. The most prominent dissidents inside Cuba now say they welcome the opening, and the State Department cautiously notes that political detentions there dropped to 178 in January, from a monthly average last year of 741. But any new tolerance is as untested as the fragile spirit of cooperation between Havana and Washington. The nominal enemies are clearly pulling together to create a political environment hopeful enough that members of Congress feel they can vote to roll back the embargo. But the exiles’ historic strength on Capitol Hill makes any such move unlikely in the near term.

For now, the most vivid sign of a new era was a seemingly mundane one: the arrival in Havana of the news conference. For longtime Cuba watchers, the spectacle of reporters questioning government officials after each session with the U.S. delegation amounted to news in itself; for decades, the government spoke only by communiqué. What’s more, while the Americans looked guarded and stiff–doubtless feeling the eyes of Miami–the Cubans appeared at ease, saying straight out what the Americans danced around. “Why not?” another senior Cuban official says, smiling. “What have we got to lose?”

–WITH REPORTING BY DOLLY MASCAREÑAS/HAVANAN

Contact us at editors@time.com.

This appears in the April 06, 2015 issue of TIME.

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