Val d'Orcia

The Val d'Orcia is a valley south of Siena, and there is one way to get around: rental car (the only practical way). Public transport runs rarely and doesn't reach every town in one day. The base is San Quirico d'Orcia, at the crossroads to the other four, about 1 h 30 by car from Florence.

The base is San Quirico d'Orcia, a village at the crossroads of the SP146 with the shortest average distance to the valley's other four towns — San Quirico–Bagno Vignoni 5 km · San Quirico–Pienza 10 km · Pienza–Montepulciano 14.3 km (14 min) · Pienza–Montalcino 22.8 km (25 min). At its centre is Horti Leonini, a Renaissance garden laid out in geometric patterns, free and open every day. From there the road first leads to Bagno Vignoni, a village with no square: where other small towns would have a market place, this one has had a stone thermal pool since the Middle Ages. Bathing in it has been banned by a municipal order since 2010, but looking is free.

The next stop is Pienza, a village Pope Pius II rebuilt as a Renaissance town from 1459 — his birthplace, and the one he returned to remake. His palace, the Palazzo Piccolomini, with a courtyard facing the valley, costs €7 (€5 reduced) to enter and includes the Diocesan Museum and the Duomo's crypt. The road between Pienza and San Quirico passes two places: the Vitaleta Chapel, reachable only on foot from a car park on the SP146, and a viewpoint on the same road, a hill lined with cypresses that's the valley's postcard image — told in more detail in the story about that view.

From Pienza a short stretch of road leads to Montepulciano, where a network of cellars cut into the rock runs beneath the historic centre. The walk-through is free, and tasting Vino Nobile, the wine the town is known for, is charged separately and depends on the cellar.

Montalcino sits on the other side of the valley, on a fortress with a view in every direction — €4 (ramparts and towers); courtyard free. The same building holds an enoteca that pours Brunello. Below the town, in the valley itself, stands the Romanesque Abbey of Sant'Antimo, built of alabaster that changes colour with the light — entry is free. On the way back to Pienza it's worth the detour to Castiglione d'Orcia, where the Rocca di Tentennano stands on a crag with the same view over the valley as the fortress, without the crowd that gathers at the better-known spots.

The valley is rarely toured on its own: Siena, to the north, runs the same loop as a full-day trip from the city, so the plan folds easily into a stay there. This loop of five towns doesn't fit into one day without a car.