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Originally an Umbrian city, it was conquered and enlarged by the Etruscans, who called it Curtun. During the 600s BC, it joined the Etruscan League.
Cortona eventually became a Roman colony under the name Corito. The origin-legends and ancient names of Cortona are described by George Dennis. In the final stages of the Gothic War (535–554), Cortona was sacked and destroyed.
Cortona became a Ghibellinian city state in the 13th century, with its own currency. From 1325 to 1409 the Ranieri-Casali family successfully ruled the town. After being conquered by Ladislaus of Naples in 1409, Cortona was sold to the Medici in 1411.
In 1737, the senior branch of the Medici line went extinct and Cortona came under the authority of the House of Lorraine.
Following the Italian Wars of Independence, Tuscany—Cortona included—became part of the Kingdom of Italy.
The foundation of Cortona remains mixed in legends dating to classical times. These were later reworked especially in the late Renaissance period under Cosimo I de’ Medici. The 17th-century Guide of Giacomo Lauro, reworked from writings of Annio da Viterbo, states that 108 years after the Great Flood, Noah entered the Valdichiana via the Tiber and Paglia rivers. He preferred this place better than anywhere else in Italy, because it was so fertile, and dwelt there for thirty years. One of Noah’s descendants was Crano, his son who came to the hilltop and, liking the high position, the fine countryside and the calm air, built the city of Cortona on it in 273 years after the Great Flood.