If ever bacchus blessed a landscape , it was the hilly terrain south of Siena. The dry clay soil is ideal for those Mediterranean plants: grape vines and olive trees. Two of Italy’s mightiest red wines hail from these parts – Brunello di Montalcino and Vino Nobile di Montepulciano. And where even the vines can’t take hold, grasslands thrive to provide rich grazing for sheep on the hills around Pienza, their milk producing the finest pecorino cheeses. Medieval hill towns, isolated monasteries, cypress-lined roads, Renaissance palazzi, Sienese School altarpieces and Etruscan tombs complete the picture.
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Morning
A 9am start in Chiusi, at the Museo Archeologico Etrusco. After learning about the Etruscans, head across the piazza to join a Labirinto di Porsenna tour. They leave every half hour, so you might be able to squeeze in a 10-minute tour of the Museo della Cattedrale as well.
Pick up winding SS146 to Montepulciano . Park at the base of town to stroll up Via Gracciano nel Corso (its name changes constantly), sampling wines along the way. Since 1858, Liberty-style Caffè Poliziano (Via Voltaio nel Corso 27-29), has served light lunches with countryside views.
Afternoon
Continuing up the main street, pop inside the Gesù for Andrea Pozzo’s illusionary painted “dome”. Next, it’s Piazza Grande (more winery shops) and then on to the Duomo.
En route to Pienza at Montepulciano’s edge, turn right (signposted) to see the Tempio di San Biagio (but skip the bare inside). Pienza is a quick stop. After admiring the altarpieces in the Duomo (see Churches Outside Florence) and giant cracks from the cliff’s settlement, tour Pius II’s Palazzo Piccolomini. An alley by the palazzo leads to Via Gozzante, a panoramic walkway out of town.
Go on to Montalcino . If you’re visiting in summer, head to the fortress for sunset views from the ramparts. In winter, make your way to the Caffè Fiaschetteria Italiana in the main square.
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Heart-stopping price tags on unique gold jewellery, inspired by ancient museum pieces.
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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.
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Classy, vaguely medieval showroom and free tasting bar for one of the top wine producers in Tuscany.
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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.
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Cast and wrought iron of great beauty in everything from candlesticks to bedsteads and fantastical chandeliers.
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The Mazzetti family’s beautiful hand-hammered copperware.
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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.
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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.
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Best selection of wine (and other food products) in town. Gorgeous setting in the airy remains of the medieval fortress.
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