Driving to Montepulciano: tolls, fuel & road trip guide

Montepulciano is a medieval and Renaissance hill town in southern Tuscany, strung along a 605-metre limestone ridge above the Val di Chiana and the edge of the UNESCO-listed Val d'Orcia. Its palaces and churches by Michelozzo and Antonio da Sangallo the Elder make it one of Tuscany's finest architectural ensembles, and it gives its name to Vino Nobile di Montepulciano, a DOCG red aged in cellars dug deep beneath the town. Autumn is its prime season: the grape harvest colours the vineyards, the summer crowds thin out, and travellers increasingly pick Montepulciano as a quieter alternative to Florence and Siena.

On a road trip Montepulciano slots neatly between Umbria and Siena, about 70 km southeast of Siena, and pairs well with Pienza 13 km to the west and the cypress-lined roads of the Val d'Orcia. Much of the historic centre is car-free, so park in the signed car parks below the walls and walk up the long main street from Porta al Prato to Piazza Grande. The climb is steep, so allow a relaxed half day, plus time for a cellar tasting if someone else is driving.

Top attractions

Piazza Grande

The town's hilltop main square, framed by the Cathedral, the travertine Palazzo Tarugi and the crenellated Palazzo Comunale, Michelozzo's town hall modelled on Florence's Palazzo Vecchio.

Montepulciano Cathedral

Santa Maria Assunta, built between 1594 and 1680 behind a never-finished brick façade, guards Taddeo di Bartolo's huge Assumption of the Virgin triptych, a masterpiece of the Sienese School.

Madonna di San Biagio

Antonio da Sangallo the Elder's 16th-century travertine sanctuary standing alone in a cypress-lined meadow below town on the road to Chianciano, an easy drive-up stop and a classic photo spot.

Vino Nobile wine cellars

Historic cellars tunnelled into the rock beneath the town's palaces, where Vino Nobile di Montepulciano DOCG ages in large barrels; many open their doors for tours and tastings, especially lively around the autumn harvest.

The Corso and Porta al Prato

The long, steep main street that climbs from the Porta al Prato gate to Piazza Grande, lined with Renaissance palaces, shops, enotecas and restaurants, with views over the vineyards between the buildings.