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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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