Allegory of Cortona; to the bottom, view of Montecarlo

Vasari's Allegory of Cortona with a view of Montecarlo below, a 1557 fresco in the Palazzo Vecchio, brings into Cosimo I's territorial map one of Tuscany's most ancient hilltop cities. Cortona, which claimed Etruscan and even pre-Etruscan foundations, was a town of considerable antiquarian prestige — its walls were among the oldest in Italy — and its inclusion in the Palazzo Vecchio series placed deep historical legitimacy at the service of Medici territorial claims. The view of Montecarlo below paired a celebrated ancient city with a smaller Florentine fortified town, maintaining the programme's structure of linking allegorical personification with documentary topographic prospect. Vasari's Cortona allegory would have reflected the town's antiquarian character through the classical gravitas of its personification, giving it a dignity appropriate to its claimed ancient origins.

The fresco technique enables the confident, rapid execution that Vasari brought to the entire Palazzo Vecchio territorial series. The Cortona allegory's female personification would be handled with the smooth, monumental simplicity appropriate to a figure claiming Etruscan antiquity, while the Montecarlo prospect below renders the actual appearance of the fortified town with the documentary attention that gives these frescoes their secondary value as historical topography.