Isla de la Juventud is the second-largest Cuban island and the seventh-largest island in the West Indies (after Cuba itself, Hispaniola, Jamaica, Puerto Rico, Trinidad, and Andros Island). The island was called the Isle of Pines (Isla de Pinos) until it was renamed in 1978. The island has an area and is 50 km south of the island of Cuba, across the Gulf of Batabanó. The island lies almost directly south of Havana and Pinar del Río and is a Special Municipality (2,419 km2), not part of any province. The Isle of Youth is, therefore, administered directly by the central government of Cuba. The island has only one municipality, also named Isla de la Juventud.
The largest of the 350 islands in the Canarreos Archipelago (Archipiélago de los Canarreos), the island has an estimated population of 100,000. The capital and largest city is Nueva Gerona in the north, and the second-largest and oldest city is Santa Fe in the interior. Other communities include Columbia, La Demajagua (formerly Santa Bárbara), Mac Kinley, Cuchilla Alta, Punta del Este, Sierra de Caballos and Sierra de Casas.
Little is known of the pre-Columbian history of the island, though a cave complex near the Punta del Este beach preserves 235 ancient drawings made by the native population. The island first became known to Europeans in 1494 during Christopher Columbus's second voyage to the New World. Columbus named the island 'La Evangelista' and claimed it for Spain; the island would also come to be known as 'Isla de Cotorras' ("Isle of Parrots") and 'Isla de Tesoros' ("Treasure Island") at various points in its history.
Pirate activity in and around the area left its trace in English literature. Both Treasure Island by Robert Louis Stevenson and Peter Pan by J. M. Barrie are rooted in part on accounts of the island and its native and pirate inhabitants, as well as long dugout canoes (which were often used by pirates as well as indigenous peoples) and the American crocodile (Crocodylus acutus) on the island.
Following the victory of the United States in the Spanish-American War, Spain dropped all claims to Cuba under the terms of the 1898 Treaty of Paris. The ownership of Isla de la Juventud was left undetermined by the sixth article of the Platt Amendment, which defined independent Cuba's boundaries, and this led to competing claims to the island by the United States and Cuba. In 1907, the U.S. Supreme Court decided, in Pearcy v. Stranahan, that control of the island was a political decision, not a judicial one. In 1916 the publication of a pamphlet "Isle of Pines: American or What?" called for the annexation or purchase of the island to settle the issue.
The Hay-Quesada Treaty, signed in 1904, which recognized Cuban ownership of the island, was ratified by the U.S. Senate in 1925 over the objections of the small colony of American planters and traders on the island.