It’s been a while since Cuba, that caiman-shaped Caribbean isle, ceased to be a place on the map. At some point, it came unhinged and floated away, transformed into a gilded reflecting pool, a repository of dreams. Those with hope or memory (true or false) called out: Here lies utopia, whether the socialist fantasy or the golden recollections of its exiles. Cuba is, or was, or could be, an exemplary nation, a veritable beacon, egalitarian and progressive.

For a small country–about 68,000 square miles and a population of just over 11 million, the navel of the Americas–this is an awesome, crushing burden. Because if Cuba inspires, it also provokes despair.

Alma Guillermoprieto’s bittersweet memoir Dancing with Cuba is about falling in love with this mythic place or, more precisely, trying to. It is also about the tense relationship between realism and idealism, a sympathetic yet ultimately unsparing account of a personal odyssey that ends not triumphantly but nonetheless extraordinarily.

Guillermoprieto is no stranger to Cuba or Latin America. A longtime contributor to The New Yorker and The New York Review of Books, she has covered the carnage between the drug cartels and Colombia’s successively impotent governments, civil wars all over Central America, the assault on Grenada by US troops, urban life and poverty in Brazil, political corruption in her native Mexico and revolutionary victory in Nicaragua.

Her report from Cuba during the Pope’s 1998 historic visit unfolded as a wrenching portrait of an ever more isolated Comandante, his military fatigues put away for the week in exchange for a designer suit, trying desperately to keep his dignity as he compromised and compromised in order to survive–and, ultimately, to hold on to power. Through her two essay collections in the last decade, Looking for History and The Heart That Bleeds, she has argued that Latin America’s politics–and indeed its political destiny–are eternally cloaked in illusion, its own identity unequivocally tied to its complex, paradoxical relationship to the United States. (Cuba’s version of this, of course, is total resistance to the United States in spite of enduring cultural and emotional ties.) While Guillermoprieto has never attempted to disguise her affinity for the leftist ambitions of Latin America’s revolutionaries, it is also true that she has never gone out of her way to massage or rationalize their prejudices and failures (and not even those that can be traced back to US actions or policies).

Dancing with Cuba is exquisitely detailed about the physicality of the place, the sensations, the conversations. Yet in the prologue Guillermoprieto is up front about the story’s sources: “I’ve retained only fragmented memories and a few concrete souvenirs that help me prove to myself, when I have my doubts, that I really did go on that journey that so thoroughly unravelled my life.” The book depends instead on documents, news reports and Guillermoprieto’s re-created moments and conversations. Many of the characters are composites, though a number of historic figures flit in and out–most notably the late Manuel Piñeiro, the Cuban spymaster, whom she portrays with a measured sympathy. Still, the book never feels impressionistic; it’s grounded in solid reporting, though the tone throughout is wistful.

Dancing with Cuba covers six months in 1970, including what is for many the pivotal moment of the Cuban Revolution: not the Bay of Pigs, not the missile crisis, but the Harvest of 10 Million Tons, a wildly ambitious campaign to produce about 3 million more tons of sugar than the country ever had, even during the exploitative “Dance of the Millions” in the 1920s or the golden age of greed under Batista. The campaign’s goal was to wipe out Cuba’s considerable debt to the Soviet Union in one fell swoop. (At the time, the island had taken out a loan from the USSR larger than its entire existing liability, essentially turning the island into the Soviet Union’s indentured servant.)

But what was at stake was much more than just long-term economic independence. It was the very heart of all the revolution could be. After all, Cuban Communism, for all its orthodoxy and very un-tropical puritanism, was considerably different from the Soviet variant: much more personal, perhaps much more–let’s just say it–Western. The Cubans wanted to loosen reliance on the Soviets because they wanted to do things their own way.

Guillermoprieto went to Cuba as a 20-year-old to teach modern dance (in a classroom with no mirrors, to avoid counterrevolutionary vanity) but wound up as witness to the historic mass mobilization of the country for the 10 million tons. Months after the campaign’s failure, the island was still feeling the depth of its wound; indeed, at the end of Guillermoprieto’s stay, the harvest of the 10 million was still too painful to talk about except in the most oblique ways.

That was a huge contrast to her arrival, when glassy-eyed, committed Cubans of all stripes talked feverishly about going to cut sugarcane in the countryside, or working double and triple shifts to relieve others so they could go cut cane. For Guillermoprieto, this kind of dedication was unheard of, exotic and alluring.

The island’s media were filled with all sorts of happy-hued stories about the nation’s superhuman effort and the certain success of the enterprise. Granma, the Cuban Communist Party newspaper, pictured a daily graph that measured the yield. The billboards exhorted: Diez Millones! (“Ten million!), A Cumplir! (Let’s do our part!”) and Comandante en Jefe, Ordene! (“Commander in chief, we’re at your command!”).

But then Murphy’s Law went into effect: Nature was unkind; it soon became evident that urban volunteers, no matter how devoted, did more harm than good with their machetes; the sugar mills, many fallow since the revolution, didn’t grind well; machinery arrived late, or not at all, or missing vital parts. The planning had been, to put it mildly, overoptimistic. Money that could have been used toward the revolution’s more essential needs–food, transportation, medicine, education–had instead been diverted to cover the vast, unexpected costs of the disaster. In the end, Cuba was burdened with a much greater, more binding debt to the Soviets than it had ever had before.

Guillermoprieto touched down in Havana on May 1, 1970, just twenty days before Castro first acknowledged the dimensions of the catastrophe in a masterful, hourslong speech before hundreds of thousands at the Plaza de la Revolución. It was then that he first uttered what is perhaps the revolution’s most chilling slogan: Convertir el revés en victoria! (“We must turn defeat into victory!”), a cry for mass rationalization.

The young Guillermoprieto, woefully ignorant not just of Cuba but of geopolitics, was thus thrust into a situation to which she could only respond emotionally. She immediately found herself as enchanted as the cultish masses by Castro’s vigor, his audacity, his rage, his unapologetic apology, his shameless display of shame. “There had never existed a more lucid, heroic man,” writes Guillermoprieto. “His physical beauty itself was the confirmation of his extraordinary spiritual energy.”

She understood too that her rapture was more the result of cadence, heat, the masses, but it didn’t matter, not then: She’d heard the siren call to revolution, trying from then on to find a way to fit the artist she was into the mold of revolutionary life and expectation. What Castro had tapped in her that day–and in so many others in his more than half a century of public life–was the desire for a meaningful life. Like many people of her generation, Guillermoprieto wanted to rebel against the status quo in those tumultuous times but was desperate for order, naïve but anxious for purpose. In the Cuban revolution, she found a paradoxical key to her dilemma: “To become a rebel was to train yourself in the discipline of absolute obedience,” particularly to Castro and, to a lesser extent, Che Guevara.

And even though she was in Cuba at the request of the revolution, doing work that it had specifically requested, she soon began to question the utility of that work, and by extension, of art. What good was any of it if it didn’t feed anyone, if it didn’t clothe anyone? By the memoir’s end, however, her questions had become as blunt as they were shattering.

Looking back over a debate from those days that appeared in the magazine published by Casa de las Américas, probably Cuba’s most important cultural institution, Guillermoprieto interprets the messages between the lines and poses the questions the Cuban intellectuals dared not articulate: “Why do I have such a strong desire to say what I think?… Why can the proletarians say what they think, while I have the revolutionary obligation to shut up?… Why is the fieldworker’s purpose accomplished when he cuts cane, and the mechanic’s purpose accomplished when he repairs the motor, while I, after having written, or painted, or criticized, have to go out and cut cane in order to fulfill my commitment to the Revolution?”

Her half-year in Cuba in 1970 is startling more than anything for the way it serves as a template of Cuban life after the revolution. Yes, there were deprivations, most directly linked to the US economic embargo, just like now. There were outrageous bureaucratic bunglings, clumsy and scandalous abuses of power (at one point, the art school director places a gun on a table to start a self-criticism meeting), condescending acts of puritanism (guards at the hotel where she stays patrol the halls to keep away her suitors, regardless of the fact that everyone is over 21, not unlike hotel security today). Back then, everyday life in Havana crept along at a snail’s pace, with all entertainment venues but the Cuban art of conversation exhausted in a matter of days–exactly like now.

“To me, what seems most bizarre about the Cuba that Fidel will leave behind,” writes Guillermoprieto in her final pages, “is its current status as a curio. The revolution that was supposed to modernize the world is now treasured as a timeless relic by tourists from a world all too horrifyingly modern.”

Time stopped in Cuba, it’s true, but it’s hard to know exactly when. And that creates a constant gush of nostalgia that is no longer the sole province of Cuban exiles. The left has its own dream of what Cuba was or should be, as enduring as the memory of falling in love for the first time. No matter how poorly it ages, you just don’t forget your first revolution.