The history of the island begins long before the pirates and the prisons, with its first aboriginal inhabitants. Indigenous peoples —belonging to the cultures that populated Cuba before the arrival of the Europeans— settled on the then Isla de Pinos, living from fishing, gathering and hunting, and using its caves as a refuge and, apparently, as ritual spaces.
The most extraordinary legacy of those first inhabitants is in the Punta del Este Cave, in the southeast of the island. There, on the walls and ceilings of a cave system, numerous rock paintings are preserved: concentric circles, lines and geometric motifs in red and black, attributed to the aborigines and considered among the most important rock art sets in the Caribbean. For their richness, they have been called the 'Sistine Chapel' of Antillean rock art.
Researchers have proposed that some of these motifs could have an astronomical or ceremonial meaning, perhaps related to the calendar or the observation of the sky, although their exact interpretation remains under study. Whatever their meaning, these paintings are a moving testimony to the presence and worldview of Cuba's original peoples, and constitute one of the great heritage treasures of the island, an open window to its most remote past.
After the arrival of the Spanish, the Isla de Pinos —as it was known for centuries— remained long on the margins of colonial development, sparsely populated and covered in pine forests and scrub. That condition of a remote land, surrounded by cays, shallows and channels in the south of Cuba, made it an ideal setting for one of the most legendary pages of its history: that of the pirates and corsairs of the Caribbean.
During the 16th to 18th centuries, when the Spanish fleets crossed the Caribbean laden with silver and gold, pirates, corsairs and buccaneers of various flags prowled these waters in search of booty. The Isla de Pinos and its surroundings offered refuges, anchorages and hideouts for these vessels, and the area filled with tales —some historical, others legendary— of raids, shipwrecks and buried treasures. That pirate atmosphere took such deep hold that it gave rise to a very widespread tradition: that the island inspired Robert Louis Stevenson's famous novel 'Treasure Island' (1883).
There is no documentary confirmation that Stevenson based himself specifically on the Isla de Pinos, and the question belongs more to legend than to proven history. But the mere fact that the tradition exists reveals just how much the island is imbued with the Caribbean pirate imagination. That legacy of adventure and mystery remains, today, part of the charm of a place that for centuries was, literally, an island of pirates in the heart of the Caribbean.
The 20th century brought the island new chapters. After a period in which, due to disputes stemming from Cuba's independence, its sovereignty was in question (finally recognized as Cuban), the Isla de Pinos received waves of immigrants —Americans who set up citrus plantations, as well as Caribbeans from other islands— who left their mark. But the most famous episode of the era was the construction of the Presidio Modelo, an enormous circular prison inspired by the 'panopticon' model, raised in the first half of the century, which came to house thousands of prisoners in very harsh conditions.
The Presidio Modelo entered Cuban history above all for one reason: Fidel Castro was confined there together with the other survivors of the 1953 assault on the Moncada barracks. Fidel spent nearly two years imprisoned on the island, before being amnestied in 1955 and leaving for exile in Mexico, from where he would organize the Granma expedition. That is why the Presidio Modelo, today turned into a museum, is a fundamental memory site of the Cuban Revolution.
After the revolutionary triumph of 1959, the island experienced a notable social transformation. Numerous schools were set up on it that hosted thousands of young students, both Cuban and from other countries, as part of internationalist educational programs. That strong youthful presence led to the island officially changing its name in 1978 from Isla de Pinos to Isla de la Juventud (Isle of Youth), by which it has been known ever since. Thus, a single territory brings together the layers of the aborigines, the pirates, the prisoners and the young people: an island with one of the most singular and varied histories in Cuba.
The island also holds a chapter of the life of José Martí, the Apostle of Cuban independence. In 1870, being barely a teenager, Martí was sentenced to forced labor for his independence ideas and, before his exile to Spain, spent a brief period on the then Isla de Pinos, at the El Abra Farm, today turned into a museum. That passage of the young Martí through the island makes it a memory site of the very origins of the Cuban nation.
The period between the end of Spanish rule (1898) and the first decades of the 20th century was especially singular for the island: its sovereignty was left in suspense. Due to the ambiguous wording of the Treaty of Paris and the subsequent U.S. intervention, for years it was unclear whether the Isla de Pinos belonged to Cuba or to the United States. In that void, numerous American settlers arrived who established citrus plantations and small communities, along with immigrants from the Cayman Islands and other parts of the Caribbean. Only with the Hay-Quesada Treaty, ratified in 1925, did the United States formally recognize Cuban sovereignty over the island.
That multiple heritage —indigenous, Spanish, pirate, American, Caribbean— gave the island a particular cultural mix, which adds to the later layers of the Presidio Modelo and the internationalist students. Today the Isla de la Juventud is a special municipality of Cuba, quiet and sparsely populated in relation to its size, that lives from agriculture, fishing, marble mining and a still incipient tourism of nature, diving and history. Its isolation, far from being just a disadvantage, has preserved an authentic character and an exceptional historical and natural heritage.