The province of Arezzo, bounding Tuscany's northeast corner, is a land of castle-dominated hill towns, misty blue mountains, and Apennine forests. Snowy-white cattle graze in the wide Chiana Valley, while light industry toils at the edges of medieval centers. In the reaches of the mountains lie tranquil hermitages such as La Verna, St. Francis's favorite spot to pray, where tradition holds he became the first human to receive the stigmata.

This is the region where the brawny, humanist Renaissance of Florence meets and melds with the intangible, hazy spirituality of Umbria's green hills. This hybrid is perfectly displayed in the works of the region's two most famous artistic sons, Piero della Francesca and Luca Signorelli, both masters of mathematical proportion and of rarefied moods and landscapes in painting. Piero is the focus of his native Sansepolcro, and one of the main draws in Arezzo, a low-key city of amiable citizens and modest art treasures. Art-rich Cortona, Luca Signorelli's hometown, is an ancient Etruscan hill town that doesn't quite fill up its medieval walls; much of the space is occupied by oversize gardens.

Arezzo province has also given us the great poet Petrarch, whose classical studies and humanist philosophy rang in the Renaissance and earned him the moniker "the first modern man," and Giorgio Vasari, architect of the Uffizi, court painter to Cosimo I, and the Western world's first art historian. Vasari brought Petrarch's movement full circle by literally writing the book on the Renaissance. It's no surprise the ultimate Florentine of the Renaissance era, Michelangelo, was born in the forested hills east of Arezzo.

The Valdichiana: The Big Valley

Cortona, Arezzo, and to the west, Montepulciano, nestle on the flanks of the Valdichiana (or Val di Chiana), a wide swath of farmland running north–south for some 100km (62 miles) through central Italy. Etruscans settled the valley 2,500 years ago, leaving behind remnants of their sophisticated civilization in Cortona, Chiusi, and other centers of their 12-city confederation.

These days the valley supplies some of Italy’s most prized beef, bistecca alla fiorentina, from Chianina cattle, along with stunning views from Cortona and the other hill towns that overlook the green and golden landscape. You can shoot through the valley on the A1 autostrada or on fast trains between Rome and Florence, but for a nice close-up look, opt for the scenic 33-km (20-mile) drive between Cortona and Montepulciano.