Cortona rises above Tuscany's Val di Chiana, commanding routes between the Tiber valley, Lake Trasimeno, and northern Etruria. Archaeology shows occupation by the late Villanovan period, and by the eighth to seventh centuries BCE the settlement had become a major Etruscan city, known as Curtun. Its elevated position supported political control of fertile land and movement through central Italy. Later writers placed Cortona among the cities of the Etruscan League, though their descriptions blend historical memory with idealized accounts.

During the fourth century BCE, builders enclosed the hilltop with roughly three kilometers of massive stone walls. Large blocks fitted without mortar followed the terrain, and the Porta Bifora preserves an ancient double gateway. Elite families constructed monumental tombs below the city, including the Meloni del Sodo. One tomb's stone stair-altar carries sculpted sphinxes and scenes of combat, revealing wealth and ritual display. The bronze Tabula Cortonensis, discovered in the twentieth century, preserves one of the longest Etruscan inscriptions and illuminates land transactions and language.

Cortona allied with Rome during Roman expansion but eventually became integrated into the republic and empire. Roman roads, gates, cisterns, and villas reshaped the territory; the luxurious villa at Ossaia developed over several centuries. The town's prominence fluctuated, and Gothic warfare in late antiquity brought destruction. Medieval inhabitants reused the Etruscan circuit as foundations for new defenses, a practical continuity that helped preserve ancient masonry. Christian institutions and a bishopric reorganized civic and sacred space within the inherited enclosure.

In the thirteenth century Cortona emerged as a self-governing commune aligned at times with the Ghibelline cause. The Casali family ruled from 1325 until 1409, sponsoring palaces, walls, and churches amid rivalry with Arezzo, Perugia, Florence, and papal forces. Ladislaus of Naples seized the town and sold it to Florence in 1411, bringing Cortona under Medici authority. Renaissance artists including Luca Signorelli worked here, while churches and elite residences added new layers without erasing the steep medieval street pattern.

Under the Medici and later Lorraine grand dukes, Cortona became a provincial center within Tuscany. The Etruscan Academy, founded in 1727, assembled antiquities and fostered scholarly attention to pre-Roman Italy. Its museum, now MAEC, preserves the great bronze Etruscan lamp, the Tabula, tomb finds, and later art. Nineteenth-century archaeology often mixed careful observation with speculative foundation myths, including tales tracing Cortona to Noah. Modern excavation and landscape survey have replaced those stories with evidence-based, still-evolving interpretations.

Today ancient walls, medieval gates, communal palaces, churches, archaeological parks, and inhabited houses form a continuous townscape. Tourism and the popular image of idyllic Tuscany support conservation but can simplify Cortona into scenery. The hill faces seismic risk, traffic constraints, erosion, and pressure on local housing. Its deepest significance lies in reuse: Etruscan defenses still support later walls; artifacts moved into civic collections shape modern identity; and contemporary residents navigate streets determined by ancient topography. Cortona remains a living city built in conversation with its buried predecessors. The archaeological park and civic museum make that continuity accessible without separating celebrated artworks from the landscape, tombs, roads, and social systems that produced them.