Sunrise on the shores of La Isla de la Juventud, or the Isle of Youth.CreditFederico Rios Escobar for The New York Times
There’s nothing like a total absence of safety measures to add a little excitement to a historical site. Within an hour of landing on La Isla de la Juventud, the Isle of Youth, I was clamoring through an underground tunnel in the Presidio Modelo, or Model Prison, Cuba’s most dreaded pre-revolutionary prison, using my iPhone as a torch and trying not to slip on wooden planks and rubble. After squeezing up a rusty spiral staircase, I emerged atop a tower at the center of an enormous circular cell building that resembled a tropical Colosseum, where a single guard would once monitor more than 1,000 prisoners at a time.
The scale was bewildering — it was one of four 1931 jail structures in the Model Prison, rising like sinister missile silos, with a mess hall at their center. Just as bewildering: the fact that nobody would stop me climbing five stories without handrails into cells with a 50-foot drop onto concrete. (One can only marvel at Cuban liability laws, or the lack thereof.) The whiff of danger helped bring the disturbing past of the Presidio, which functioned from the late 1920s to 1967, to vivid life. A small museum was filled with startling photos of the prison’s brutal inner life, when it was run by wild convict gangs with weapons crafted from iron spikes and nails. But the most striking sight of all came when I entered the former hospital ward, which in the 1950s was reserved for political prisoners. Posted on a wall was a mug shot of its most notorious inmate, Fidel Castro — without a beard.
Like the few other visitors to the Presidio that day, I had to stop and stare at the clean-shaven, well-fed features of Prisoner 3895, who, instead of his famous Old Testament whiskers, sported a scraggly pencil mustache. It was a sudden step back into a barely remembered Cuba, when Fidel was not yet “Fidel.” Today, the image of the hirsute Castro in military khakis is so ingrained in the popular imagination that he seems to have sprung ready-made onto the world stage when the revolution succeeded in 1959. But almost nobody had heard of him six years earlier, in 1953, when, as a 27-year-old lawyer, he began his rebellious career with an attack on a military barracks in the city of Santiago. Castro had hoped this would spark an uprising around Cuba, but it failed dismally. Many of his 160 or so followers were tortured and executed and most of the rest hunted down. He was given a 15-year sentence and sent with 25 compañeros to La Isla.
It was in this prison, improbably enough, that the Cuban revolution was effectively planned. The dictator Fulgencio Batista made the mistake of placing all the conspirators together in the hospital wing, and they proceeded to treat it as a revolutionary boot camp, congregating for daily lessons on politics and conducting secret communications with supporters around Cuba. “What a fantastic school this prison is!” Castro wrote gleefully in a letter. “From here I’m able to finish forging my vision of the world …” After four months, he was removed to solitary, but even there he kept in touch with his men using messages written in lemon juice that were smuggled in cigars or mashed potatoes. He also secretly wrote a tract called “La Historia Me Absolverá” (“History Will Absolve Me”), a recreation of his trial defense speech that was spirited page by page to Havana and published as a rousing call to arms. By the time popular opinion led to the men’s release in 1955, after serving less than two years of their sentences, the once-disorganized rebel group had become a coherent political cell, with a support network and a clear plan for a guerrilla war.
The Presidio was closed a few years after Castro’s victory in 1959, and is now maintained as a shrine to the revolution’s early struggle, with photos of each prisoner over his bed. It’s a tribute to the resilience of the young rebels who — whatever their later faults once they took power — took on the brutal Batista dictatorship at great personal risk. The aura of idealism becomes particularly poignant today, as Cuba’s revolutionary dream has become as battered as the corrugated iron ceiling of the Presidio itself — its gaping views of the sky letting in the beating sun, the tropical rain and chirping green parrots.
As I discovered over the next three days, almost every corner of Isle of Youth — or simply La Isla, as it is referred to by residents — hides an equally eccentric saga. Located off the south coast of the main island, the largest of the nation’s 4,000-odd offshore cays and islands, it has been specializing in oddity ever since Christopher Columbus weighed anchor here to find provisions on his second voyage in 1494 and was mystified by its monstrous crocodiles and raucous bird life. Soon after, pirates hid in its coves, making it an inspiration for Robert Louis Stevenson’s “Treasure Island.”
The stories become even more outlandish in the 20th century. Following the Spanish-American War, the Isle of Pines (as it was then known) became an American territory in the early 1900s, and settlers with names like Chuck and Martha dug citrus orchards in townships called McKinley, Columbia and San Francisco Heights. It was on its return to Cuba in 1924 that the island entered its Devil’s Island phase, with the Model Prison built as a rare example of the notorious Panopticon — in which myriad inmates could be watched by a single guard — conceived by the 18th-century British philosopher Jeremy Benthem. Then, at the height of the revolution in 1978, Castro returned to the island as Maximum Leader and declared that it would become a unique Communist education center, where high school students from Third World countries could study in a sun-kissed paradise.
Today, La Isla is embarking on yet another reinvention — as an ecotourism destination. A few entrepreneurs are making modest attempts to lure foreign travelers and their hard currency to its pristine beaches and offshore coral reefs, which are among the best preserved in the Caribbean. “What’s important to marine life is scale, and Cuba is so big,” said David E. Guggenheim, an American marine biologist who founded a nonprofit called Ocean Doctor, who I first met in Havana during a conference on marine protection. “Size matters! Reefs need large integrated ecosystems to survive.”
Cuba is unique in the Western Hemisphere for its near-total lack of coastal development, he explained. Since the collapse of the U.S.S.R. in 1991, Cuban farmers have had no access to pesticides or fertilizers, so there is none of the chemical flow-off that can devastate marine life. “Farmers on the Isle of Youth have been forced to practice organic agriculture,” Mr. Guggenheim said. “Most of them don’t even have tractors. It’s amazing that such a thing is possible in the 21st century.”
Still, it’s an uphill battle to attract travelers, since La Isla is today so obscure that even most Cubans know nothing about it. I had only the haziest idea of what I might find there when I turned up at the Havana airport before dawn to catch a propeller plane. A half-hour later, we were banking over the comma-shaped island and landing at its only town, Nueva Gerona. I was relieved to find that La Isla had lost none of its oddity: We were met at the tiny airport by a nurse in white uniform who screened us all for fevers.
While it’s no longer true to say that Havana is “stuck in the 1950s,” an argument can be made for La Isla — perhaps the 1850s. There are no streetlights in Nueva Gerona, no buildings taller than two stories, and almost the only traffic is horse-and-buggy. On its sleepy pedestrian boulevard, the main cultural attraction is a map of Cuba made from rusty horseshoes. At dusk, teenagers make out in the Park of the Heroic Guerrilla, while older couples promenade arm in arm and take romantic carriage rides holding hands. After dark, everyone converges on the boulevard to hear live salsa and dance, the only concession to the 21st century being a decent sound system.
I checked into a casa particular, a private guesthouse, a cozy home decorated with ceramic fish and boasting a sunny billiards room. It was run by a voluble woman named Diami, who whipped up fortifying breakfasts of sweet black coffee, farm eggs and chunks of mango, the most succulent of the tropical fruits that grow like weeds on the fertile island. (“We call these American mangoes because they are plump and red,” she deadpanned). The islanders spoke with cheery resignation about being forgotten by the world. “We suffer from double insularity,” a wiry, chain-smoking poet named Tony Ramírez said excitedly, when I met him at one of the few restaurants, El Galeón (which, as its name suggests, was shaped like a galleon). “We feel very far from the rest of Cuba, which is already cut off from the world.” Tony drew inspiration for his writing from being in un mundo aparte, a world apart, he said, but worried about the island’s vulnerability: “Communications are a problem. One puff of wind, let alone a cyclone, and we’re on our own.”
Clearly, nobody comes to La Isla for the night life: By 9 p.m., Gerona was a ghost town. The next morning, I was ready to sally forth into the countryside, but there were only two jeeps for hire, I learned, and both were broken. Luckily, I found a taxi driver named Ray drowsing by the plaza in his battered blue Lada. Soon we were chugging along empty, palm-fringed roads past limestone protrusions called mogotes — the same sensuous rock formations that has turned the Cuban province of Pinar del Río into a busy tourist destination, but here stand solitary and unseen. Marble is quarried from their flanks in such great quantities that many peasant huts have the polished stone for their floors.
On this island of broken dreams, the ruins of the revolutionary schools of the 1980s litter the landscape like giant Lego blocks. Castro traveled here to personally inaugurate the idealistic education program in 1978 and change the name of the Isle of Pines to Isle of Youth — which has a Communist Utopian ring but also evokes the mad quest of Ponce de León for the Fountain of Youth. (Confusingly, islanders are still called Pineros in Cuba.) Within a decade there were 61 schools on the island serving 35,000 students, mostly from Africa. After the Soviet Union crumbled, funding was cut and the students vanished as if they had never been here. A 2008 hurricane did the rest by gutting the schools.
Although most of the Soviet-style structures are in poetic decay, three still function for locals. We called in at Escuela No. 8, the Clara Zetkin School, named after a German Marxist theorist and now filled with island children. The walls are still decorated with a Cold War mural, the Cuban version of “if you see something, say something”: A giant eye hovers over a map of the island with an illustrated list of dangers that pupils should report, including “enemy aircraft,” “enemy parachutists” and “dead animals.”
But the most unexpected historical site is a peaceful field only a few miles from town. El Cementerio Americano, the American Cemetery, is the last ghostly reminder of the quarter century when the United States ran La Isla as a virtual colony. After the Spanish-American War of 1898, Cuba was put under United States military rule until 1902; in the treaties that followed, ownership of the Isle of Youth was left so vague that American companies bought up most of the arable land and opened it to settlers. To the fury of Cuban patriots, farmers from Iowa and California moved here assuming it would become an official part of the United States. (One pamphlet pushing for full annexation was called: “The Isle of Pines: American or What?”) Tourists traveled from New York to loll by its mineral pools; the poet Hart Crane stayed one summer and was fascinated to experience a hurricane, which inspired the poem “Eternity.”
When Congress reluctantly gave La Isla back to Cuba in 1924, most settlers left in disappointment, but those who stayed are buried in the American Cemetery. I strolled with the bemused taxista Ray through the lonely field in golden light, reading names from overgrown gravestones — one shaped like a tree trunk — and pausing at a gazebo until the mosquitoes drove us out.
It was time to head to the island’s wild south, a jigsaw of protected landscapes informally called the Siguanea Nature Reserve where caves are filled with pre-Colombian carvings, sea turtles lounge by the beaches and reptiles bask in the swamps. My plan was to visit the evocatively named village of Cocodrilo (crocodile) with Dr. Guggenheim, who since 2015 has worked with a local group there called Red Alerta to protect its pristine coral reefs. It is a singular Cuban-American joint venture. His Washington-based N.G.O., Ocean Doctor, provides equipment and trains villagers to work as guides instead of fishing illegally — a standard ecotourism model in other parts of the world, but a radical departure in Cuba, where the economy is still mostly state-run and grass-roots activism is discouraged.
“As fearful as we are of thousands of Americans going down to Cuba and recreating the mass tourism model that destroyed much of the Caribbean,” he told me in Nueva Gerona, “tourism has to be part of the solution.” (Because it is research-based, the Red Alerta program has been unaffected by recent changes to travel for American citizens, but visits have to be arranged through an authorized travel agency or Ocean Doctor.)
But La Isla has not shaken off its Cold War past. The Cuban military monitors the various southern nature reserves, and we soon discovered that the whole area had been declared off-limits — no explanation given. The word on the street in Nueva Gerona was that the military was conducting antidrug sweeps along the coast. True or not, there would be no Cocodrilo for us. Time for Plan B. We decided to head to El Colony, the island’s only real hotel, which had the misfortune to open the week before the revolution in 1959 and somehow managed to survive the following decades on the dribble of tourism to Cuba in following decades, mostly from the Eastern bloc. At the small marina there, we hired a boat to take us to the reserve’s limits.
Soon we were motoring south with a dive master and a cook. Our first mission was to snorkel off a popular beach called Punto Francés, where two years ago Dr. Guggenheim had seen intact expanses of elkhorn coral, a barometer of reef health. Even an amateur like me could tell that all was not well below the waves. “That is a wonderful example of a reef that is 90 percent dead,” Dr. Guggenheim said with a sigh, as we dried off back on board. There had been some bleaching from climate change, he explained, but the main culprit was overfishing, which led to the coral being slowly covered in slimy green algae. “We treat fish like crops to be harvested,” he said, “but they have important jobs to do in the ecosystem. One of them is grazing on algae, which keeps reefs clean.”
Things improved radically when we dove to a remote site named El Reino de la Sahara, the King of the Sahara. Rays of sunlight burst down on reefs that were surging with life like underwater cities, including brilliantly colored sea fans and flamingo tongues. A moray eel patrolled the shallows and there were expanses of thriving elkhorn coral. “That reef was 90 percent healthy, or better,” Dr. Guggenheim rejoiced. “But Cuba is in the balance. It could go either way. The good thing is that it has the legal protection,” he added, noting that 25 percent of Cuba’s waters are protected — a higher percentage than the United States, he said (Castro promoted marine protection after he met Jacques Cousteau in the 1980s and became an avid scuba diver). “But it doesn’t have enforcement.”
As we motored back to El Colony, Dr. Guggenheim stared out at the sea meditatively. Even in this pristine location, we can only imagine what the Caribbean must have been like when the first Europeans saw it, he mused. “Only three percent of sea turtles are left today. But when Columbus arrived on his fourth expedition, his son wrote that they saw turtles in such vast numbers that they covered the sea.’ Man, I would like to have seen that.”
All over La Isla, conversation always returned to Castro, the larger-than-life figure who had been its most notorious (if unwilling) resident, and whose grand plans in the 1970s created its golden age as a tropical youth camp. In one private restaurant, La Casa de Toti, the eponymous owner, known only as Toti, told me how his grandfather was sent to the Model Prison for murder and met Castro there in the 1950s. Along with many other inmates, he was freed a few months after the guerrillas rode into Havana in early 1959. “So my grandfather was always a big fan of Socialism,” he said with a why laugh.
The air of melancholy left by so many vanished dreams was present even when I decided to climb a remote mountain known as La Loma on my final morning, to get a glimpse of the island’s hard-to-visit south. To get there, I went to meet a farmer-turned-guide Arcadio Castro (no relation), who wore a tattered T-shirt and lived in a marble-floor shack roamed by livestock and piled high with home-bottled mango pulp.
A summer heat wave was descending: By 9 a.m., it was already 95 degrees and 100 percent humidity when Arcadio started hacking the overgrown trail with his rusted machete. Yellow butterflies flitted around us as he fondly remembered the day Fidel Castro visited his high school in 1978. The children were all astonished to see the Maximum Leader bounce a basketball up the stairs to their playground and sink it without effort. (He had been a sports champ in his youth.) In the heyday of the revolution in the 1980s, Arcadio had also served in the Cuban army in Angola and he reminisced about the monstrous bugs he found in Africa. As we climbed, there were glimpses between the palms trees of empty green plains leading to distant mogotes.
By the time we reached the summit, sweat was pouring from us in streams and I was half delirious. The view to the southern nature reserves turned out to be entirely overgrown; Arcadio admitted that he hadn’t taken anyone up here in months. I didn’t mind. It was oddly comforting to see these remote heights being reclaimed by the wild. The island’s man-made hopes have been repeatedly dashed, but hopefully nature will prove resilient.
If You Go
There are twice daily flights to the Isle of Youth from Havana on Cubana (cubana.cu), the national airline, but they can book up way in advance. Allow a night in Havana before and after the flight in case of cancellations. New travel restrictions imposed by the Trump administration mean that American citizens traveling as tourists should go through an authorized travel agent to ensure compliance (although travel does not need to be in a group, and 12 other categories of travel, such as educational or professional research, are unaffected). Flights and tours can be booked through an international agency such as Cuba Travel Network (cubatravelnetwork.com) or the United States-based Cuban Educational Travel (cubaeducationaltravel.com). On the ground, the best island agency is Ecotur (53-46-32710; firstname.lastname@example.org). OceanDoctor is expecting to offer educational tours to the wild southern coast in spring (oceandoctor.org/cuba-travel-program/#upcoming; around $5,000 for seven- to 10-day trips.)
Where to Stay
l Colony (rates start at $63 for a single person with half board, hotelelcolony.com/en/) is a good base for divers but quite removed from other attractions — and being state-run, has wretched food. Far more satisfying is to stay in one of the casas particulares, private guesthouses, in the town of Nueva Gerona and make day trips. I stayed in the quaint and comfortable Villa Gerona, run by the feisty Diami, (53-4631-2962, villagerona.com; rooms starting at $23). Others can be found on Cuba Junky (cuba-junky.com).
Where to Eat
The best restaurants on the island are the Buena Vista (Calle 39 #2416A, 53-5503-2666), which has a patio overlooking the Boulevard, and the private paladar Casa de Toti (Calle 3ra #401 near the Presidio Modelo, 53-5277-5565).
Tony Perrottet, the author of “Pagan Holiday,” is working on a book about the Cuban guerrilla war.