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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.

In the 15th century, Pope Pius II hired Rossellino to revamp his home village with an assemblage of buildings on the main square, including a retro-Gothic town hall, a palace for the bishop (housing the Museo Diocesano of paintings by Pietro Lorenzetti, Vecchietta and Bartolo di Fredi), a papal palace (great hanging gardens) and a Duomo (see Pienza’s Duomo). High Street Corso Rossellino is packed with wine and cheese shops.

The hometown of Tuscany’s mightiest wine, Brunello (see Brunello di Montalcino), is a small but proud burg, with an excellent wine shop in the ruined 14th-century Fortezza, a split-level main square and a lanky 1292 tower. The Museo Civico e Diocesano houses paintings by Simone Martini, Sano di Pietro and Vecchietta, and polychrome wood statues by Francesco di Valdambrino.

French-style Romanesque abbey church in a beautiful countryside setting.

The fine Museo Archeologico Nationale Etrusco in Chiusi contains bucchero (black Etruscan earthenware), bronzes, anthropomorphic canopic jars and even a few 2nd-century BC painted funerary urns. Apply here to visit the best decorated tombs in the valley.

The 12th-century Duomo is swathed in trompe-l’oeil frescoes (1887–94) that look like medieval mosaics. Next door, the Museo della Cattedrale preserves 15th-century illuminated scores from Monte Oliveto Maggiore. Meet here for guided visits to the Etruscan-carved “Labirinto di Porsenna” tunnels.

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.

Friendly little farming town with amazing Romanesque carvings on the Collegiata’s trio of 12th-century portals: fantastical creatures, stacked arches, tiny telamons and thin columns “knotted” in the centre and resting on toothless lions. Inside is a sumptuous Sano di Pietro altarpiece.

Within its 14th-century walls, next to the travertine Romanesque Collegiata, Asciano’s Museo d’Arte Sacra contains Sienese works by Ambrogio Lorenzetti, Segna di Buonaventura and Francesco di Valdambrino. The minuscule Museo Etrusco’s 3rd- to 5th-century BC painted vases are installed in a deconsecrated church.

Little more than a square of houses around a vast, Medici-built portico and basin steaming with naturally carbonated, volcanically heated waters. St Catharine bathed here for her scrofula (lymphatic tuberculosis), Lorenzo the Magnificent for his troublesome arthritis, but sadly the pool is no longer suitable for swimming.

The tiny historic centre shelters a good Museo d’Arte Sacra, with Sienese School works by Duccio, Sano di Pietro and Matteo di Giovanni, who also left a Madonna and Child in the 14th-century Santi Piero e Paolo church.