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 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 James Matthew 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 Cuba's boundaries, and this led to competing claims to the island by the United States and the now-independent 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 1925 a political settlement was finally reached. The Hay-Quesada Treaty, which recognized Cuban ownership of the island, had been signed between the two countries in 1904. Twenty-one years later, over the objections of the small colony of American planters traders on the island, it was ratified by the U.S. Senate
