Italy's Arezzo, Cortona, Sansepolero & the Val di Chiana

Hanging onto a steep hillside first inhabited by the Etruscans, Arezzo is one of the most peaceful Tuscan cities, with a pleasant pedestrianized historical center that is a pleasure to walk around. The Aretines (inhabitants of Arezzo) are a pretty proud lot (the Florentines like to call them "snobby"). Their important commercial and military history has generated a local character so distinct from that of their Tuscan neighbors that the province is often referred to as the "anticamera dell'Umbria" (Umbria's lobby). The city's cultural and artistic heyday came at the end of the 12th century when it was established as an autonomous commune under Bishop Guido Tarlati (under whose rule were built its most beautiful monuments). Adhesion with the Ghibellines saw the start of violent skirmishes with the Florentine Guelphs. The Florentine victory at Campaldino brought Arezzo under the control of Florence and later of the Medici. The Valtiberina (or Upper Tiber Valley) occupies the easternmost edge of Tuscany, on the border with Umbria, Emilia-Romagna and Mare. Much fought over between papal Rome and imperial Florence, this countryside is peppered with castles and monasteries. It is the homeland of Michelangelo (Caprese) and Piero della Francesca (Sansepolcro), plus hilltop medieval villages like Anghiari, Badia Tedalda and Monterchi, river centers like Pieve Santo Stefano, and abbeys, convents and sanctuaries. Cortona boomed as a tourist destination after the publication of Frances Mayes' Under the Tuscan Sun and with a recent film adaptation inspiring a new generation of visitors to the medieval hilltop town, things aren't likely to change for a while. The Etruscans dwelt in the region for centuries, leaving remarkable signs of their presence in the surrounding necropoli. The Romans came next, turning Cortona into a significant trading center until the Goths came along and destroyed the whole lot. It re-grew as a free comune in the 11th century before being sold by the King of Naples to the Florentine Republic but, apart from a few Renaissance palazzi, the town is truly medieval at heart.