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This quietly chic peninsula is really an almost-circular island, connected to the Tuscan mainland by causeways.

Nestled amid a cypress-covered hilltop in the crete senesi landscape of eroded clay and limestone bluffs is a 1313 Benedictine monastery. It guards a cloister frescoed with the Life of St Benedict , a masterpiece of High Renaissance narrative painting by Signorelli (the west wall’s eight scenes; 1497–98) and Sodoma (the other 25 scenes; 1505–1508). Sodoma inserted a self-portrait in the third scene, his pet badgers at his feet.

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.

This posh, if overbuilt, thermal spa town is worth staying in to experience one of the 19th-century, Grande Dame hotels. Above the town, medieval Montecatini Alto is a favourite escape for summer breezes and cappuccino on the piazza, while nearby Monsummano Terme has the attraction of natural cave saunas.

Hill town with buildings by major Renaissance architects and Tuscany’s second greatest wine, Vino Nobile (see Vino Nobile di Montepulciano). Via Gracciano nel Corso is lined with Renaissance palazzi by the likes of Vignola and Antonio Sangallo the Elder, but also look out for Palazzo Bucelli (no. 73), its base embedded with Etruscan urns. Piazza Grande is flanked with palaces by Sangallo, the town’s Duomo and the Palazzo Comunale, which is Michelozzo’s tribute to Florence’s Palazzo Vecchio. Inside the Duomo are sculptures by Michelozzo that once formed a single tomb, while the gilded altarpiece is Taddeo di Bartolo’s Sienese Gothic masterpiece of 1401.

Set on a patch of grass below the town walls is Sangallo’s geometrically precise Tempio di San Biagio (1518–34), the best example of the High Renaissance trend towards Greek Cross churches.

The town rises from a Medici city gate to the hilltop Piazza Grande with its crenellated Michelozzo-designed Palazzo Comunale and brick-façaded Duomo. Along the way, the main street passes Renaissance palaces, 19th-century cafés and dozens of wine shops where the samples of grappa and Vino Nobile (see Wine Houses) flow freely. You can also visit the cellars beneath the town.

High Renaissance masterpiece of proportion (see Montepulciano).

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.

Tuscany’s greatest protected parkland. Coastal Monti dell’ Uccellina (“Mountains of the Little Bird”) is a large area of pine forests, teeming with boar, roe deer and porcupines, bird-filled marshland to the north, as well as tracts of pristine beach. A pack of wild horses and roaming long-horned white Maremma cattle are looked after by Butteri cowboys. Buses from Albarese take you to the park’s centre.

Ferdinando I founded this inlaid stone workshop, also Florence’s chief laboratory for art restoration.