Day trips from Siena

If only half a day is free, Monteriggioni fits into it with no changes and no car. A full day without your own transport only stretches to San Gimignano, on a direct bus; Montepulciano needs a train plus a connecting bus into the centre, and the three Val d'Orcia villages — Pienza, San Quirico and Montalcino — are only seen by car, since no single line links them into one trip.

Monteriggioni is a village Siena built between 1213 and 1219 as a defensive outpost against Florence. Its wall, about 570 metres round, carries fourteen towers at close to their original height — a rare case in Tuscany, where most defensive walls were pulled down or shortened over time. Dante described them in the early fourteenth century in the Inferno, comparing the giants at the bottom of hell to the towers crowning Monteriggioni. Inside the walls is one square and two churches; half a day is enough.

130/131 bus (Autolinee Toscane), Colonna di Monteriggioni stop takes about 20 min and stops at Colonna di Monteriggioni, a few hundred metres from the gate. The return fare is €4.

When to goWhen a drive through these hills is most pleasant:The best time to visit Siena →

San Gimignano is known for the medieval towers wealthy families built against one another as a show of power; there used to be around seventy-two of them, fourteen survive today. The whole historic centre has been on the UNESCO list since 1990. The town is also home to Vernaccia, which in 1966 became the first Italian wine to carry a DOC label and has held DOCG status since 1993.

GuideA full day in San Gimignano, hour by hour:San Gimignano →

130 bus (Autolinee Toscane), direct takes about 1 h 15 each way. The return fare is €16.20, and the towers, museums and a glass of Vernaccia take a full day.

Where to stayThe same bus runs through Terzo di Camollia, where it also stops on the way in from Florence:Where to stay in Siena →

Montepulciano is reached by train on the Siena–Chiusi line, about 1 h 20 (train ~1 h plus the connecting bus), changing to the local "Montepulciano Link" bus up to the hilltop centre; the return fare is €19.40. The town is known for Vino Nobile, Italy's first red wine to carry DOCG status, and for the Tempio di San Biagio, a temple the architect Antonio da Sangallo the Elder began building in 1518, with a Greek-cross plan and a dome, standing alone in a meadow below the walls.

The centre, a tasting and the temple take a full day; the last connection back leaves in the early afternoon, so the day is planned backwards from it.

Pienza, San Quirico and Montalcino don't fit into one trip by public transport — car only, and that's the reason, not a choice. The same white gravel roads that link the villages have carried the Strade Bianche professional cycling race since 2007, which starts and finishes on the Piazza del Campo in Siena every early March — so this valley stays tied to the city even outside the sightseeing season.

GuideThe Val d'Orcia as a trip of its own, with a base in the valley:Val d'Orcia →

All three villages and the driving between them take a full day. The order runs from the nearest out: Montalcino, then San Quirico, then Pienza.

1 dayThe same city, hour by hour, for when a trip doesn't fit the schedule:Siena in 1 day →

Hidden gemsThe university and the city's own stories, for a day without a day trip:Siena beyond the Campo: a saint's head, a fortress and a city full of students →