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A mountainous peninsula covered in ilex and olives, and rimmed with isolated beaches. The trendier of its two towns is southerly Porto Ercole, where Caravaggio gasped his last. It retains a fishing village air. Porto Santo Stefano is a slightly larger, more middle-class resort town and main fishing port.

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.

A gorgeously frescoed monastery in the hills, offering single and double rooms with private baths (Easter–Oct), and selling honey, herbs and wines.

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.

A little overbuilt, but still the best place in Italy for grandiose, Liberty-style thermal establishments: drink Terme Tettuccio’s waters for your liver, wallow in Terme Leopoldine’s mud for your skin. Also take the funicular to the medieval hill town of Montecatini Alto.

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.

After a week of medieval pageantry, festivities and feasting, costumed two-man teams from Montepulciano’s eight neighbourhoods prove their racing prowess by rolling hefty barrels up this hill town’s meandering, often steep main street to the piazza at the top.