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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.

Morning

Start with the Duomo group, especially if it’s winter, as the museum closes in the afternoon. Explore the Gothic nooks and Baroque crannies of the cathedral itself first, then pop across to Santa Maria della Scala.

Don’t skip the Museo Metropolitana (see Museo Metropolitana: Duccio’s Maestà) with works by Giovanni Pisano, Donatello and Duccio, plus fabulous views from the unfinished façade wall.

Descend the stairs to see the Baptistry before heading back around the other side of the Duomo for lunch at Antica Osteria da Divo .

Skip dessert so that you can pick it up at Bini pastry shop around the corner at Via dei Fusari 9–13 (don’t eat it just yet).

Afternoon

Stroll down Via di Città, where there are plenty of attractive shops on your way to II Campo (see Piazza del Campo). Either eat your pastries from Bini or grab an outdoor table at Bar II Palio, Piazza del Campo 47–9. Order a coffee or glass of wine, and drink in the ambience of one of the loveliest squares in Italy.

Head inside the Palazzo Pubblico for the Museo Civico displaying Siena’s greatest Gothic art. Exit the Campo on the north side to join the locals for a bracing espresso or Campari at famed café Nannini before continuing up Via Banchi di Sopra as part of the lively evening passeggiata .