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An Etruscan city, then ancient Roman pottery centre, Arezzo was later home to Guido Monaco, who invented modern musical notation in the 11th century, the poet Petrarch (1304–74) and Giorgio Vasari (1512–74), architect and author of the first art history text, Lives of the Artists .

The town’s centre is the broad, sloping Piazza Grande. The bell-tower, façade and medieval Calendar reliefs of the 12th-century Santa Maria della Pieve are Lombard-Romanesque style, but the altarpiece (1320) is pure Sienese Gothic courtesy of Pietro Loren-zetti. The Duomo has excellent stained-glass windows by French master Guillaume de Marcillat, and a fresco by Piero della Francesca. The 14th-century San Francesco is graced with Piero’s recently restored Legend of the True Cross (1448–66).

San Romulado established this Benedictine community in 1012, though the monastery is 15th century and the Vasari-decorated church 16th. One mile (1.5km) up a forest path lies the secluded hermitage (only men admitted), a tiny village of monkish cottages alongside a Baroque church.

Off Piazza del Municipio, Sant’Agostino has a trove of paintings, starring the 13th-century St Francis by Margheritone d’Arezzo, Gaddi’s Madonna and Child and Bartolomeo della Gatta’s St Francis Receiving the Stigmata .

Cortona is the quintessential Tuscan hill town with its Etruscan tombs, medieval alleys, Renaissance art and excellent restaurants.

St Francis himself founded this clifftop monastery, and a Baroque frescoed corridor passes the now-enclosed cave where he slept. At the end of the corridor is the Cappella delle Stimmate, which was built over the site where the saint received his stigmata in 1224. For a sense of the saint’s La Verna unencumbered by buildings, follow the path to Sasso Spico, another rocky outcrop where the holy man prayed.

Tiny, elliptical town, whose single street spirals to the 16th-century Collegiata church. Behind the church, the Palazzo Comunale houses a museum with late Gothic Sienese paintings and a 2m (6ft) high gold reliquary dubbed Tree of Lucignano (1350–1471).

This ceramics town has a small pottery museum and Santa Chiara church, which contains early works in terracotta by native sculptor Andrea Sansovino (1460–1529). He also carved marble (a sarcophagus in the Pieve), designed the loggias and cloisters of Sant’Agostino and collaborated with Antonio da Sangallo the Elder on the Loggia dei Mercanti, opposite Sangallo’s lovely Palazzo di Monte.

Piero della Francesca’s masterwork takes the unusual subject of a heavily pregnant Virgin Mary, her tired face and drooping eyes revealed by angels pulling back the curtains. It was painted in a nearby chapel, where it became a pilgrimage focus for pregnant women until it was removed to this small museum.

The sweetest Casentino hill town, dominated by the Castello dei Conti Guidi (1274–1300), built by Lapo and Arnolfo di Cambio, the latter architect of Florence’s Palazzo Vecchio. Inside is a chapel, frescoed by Taddeo Gaddi.

Medieval town with a reputation built around Buitoni pasta and home-grown genius Piero della Francesca. The Museo Civico houses (alongside works by Signorelli and natives Santi di Tito and Raffaellino del Colle) Piero’s Madonna della Misericordia (1445–62), San Giuliano fresco fragment (1455–8), and the compelling Resurrection .