La Isla's star-studded history starts with its first settlers, the Siboney, a pre-ceramic civilization who came to the island around 1000 BC via the Lesser Antilles. They named their new homeland Siguanea and created a fascinating set of cave paintings, which still survive in Cueva de Punta del Este.

Columbus arrived in June 1494 and promptly renamed the island Juan el Evangelista, claiming it for the Spanish crown. But the Spanish did little to develop their new possession, which was knotted with mangroves and surrounded by shallow reefs.

Instead La Isla became a hideout for pirates, including Francis Drake and Henry Morgan. They called it Parrot Island, and their exploits are said to have inspired Robert Louis Stevenson's novel Treasure Island.

In December 1830 the Colonia Reina Amalia (now Nueva Gerona) was founded, and throughout the 19th century the island served as a place of imposed exile for independence advocates and rebels, including José Martí. Twentieth-century dictators Gerardo Machado and Fulgencio Batista followed this Spanish example by sending political prisoners – Fidel Castro included – to the island, which had by then been renamed a fourth time as Isla de Pinos (Isle of Pines).

As the infamous 1901 Platt amendment placed Isla de Pinos outside the boundaries of the 'mainland' part of the archipelago, some 300 US colonists also settled here, working the citrus plantations and building the efficient infrastructure that survives today (albeit a tad more dilapidated). By the 1950s La Isla had become a favored vacation spot for rich Americans, who flew in daily from Miami. Fidel Castro abruptly ended the decadent party in 1959.

In the 1960s and 1970s, thousands of young people from across the developing world volunteered to study here at specially built 'secondary schools' (although their presence is almost non-existent today). In 1978 their role in developing the island was officially recognized when the name was changed for the fifth time to Isla de la Juventud (Isle of Youth).