Day Trips from Siena to Hill Towns and Vineyards

October 29, 2026

Where to go for a day from Siena

The countryside around Siena is the draw: walled hill towns, wine villages and an abbey without a roof. How easy each is depends on whether you have wheels. This page groups the options by half-day and full-day, then says plainly what needs a car.

Half-day outings

Monteriggioni is the closest, 15 km north-west by the RA3 road, about 15 minutes in a car. The 13th-century circle of walls, topped by 14 towers, was built by Siena against Florence and appears in Dante’s Inferno. Buses on lines 130 and 131 stop at La Colonna, from where it is a walk of roughly 500 m. A walk along the ramparts costs about EUR 5 on older listings and EUR 4 on a municipal tariff, and winter maintenance closures happen.

San Galgano is 32 km south-west, about 35 minutes by car. The 13th-century Cistercian abbey stands roofless in a field. On the hill above, a round chapel at Montesiepi holds the sword that the knight Galgano drove into the rock in 1180, and entry there is free. There is no usable bus, so you need a car or a taxi. Abbey admission differs between sources, so check on arrival.

Full-day outings by bus

San Gimignano, 40 km north-west, is the one big hill-town day trip that works on public transport. Autolinee Toscane line 130 goes via Poggibonsi. Fares are EUR 8.10 booked ahead or EUR 10 on board, the journey takes 1 hour 15 minutes up to 2 hours, and there is no railway station. Fourteen medieval tower houses remain, as does the frescoed Collegiata, and the Torre Grossa rises 54 m. Vernaccia white wine is the local pour. Check the last bus before settling into dinner.

Full-day outings that need a car

Val d’Orcia: Pienza, San Quirico d’Orcia and Bagno Vignoni, 50 to 55 km south by the Via Cassia. Pienza was laid out as an ideal Renaissance town by Pope Pius II, and its Palazzo Piccolomini looks over the valley. In San Quirico, the geometric Horti Leonini gardens are free. At Bagno Vignoni the old thermal pool in the square is viewed from its edge.
Montalcino: 42 km south, famous for Brunello, and with a 14th-century fortress. Sant’Antimo Abbey is about 10 km beyond.
Montepulciano: 65 km south-east, about an hour. Cellars under the palaces, such as Cantina De’ Ricci, offer tastings, and Vino Nobile is the wine. The church of San Biagio sits below the town.

Buses to the Val d’Orcia exist but are thin: line 112 makes a few journeys a day on weekdays and Saturdays, none listed on Sundays, and Pienza takes about two hours with a change at Buonconvento. Do not plan to see several villages this way.

Florence in a day

The 131R coach takes about 75 minutes at roughly EUR 10.90 one way and stops at Via Tozzi near Piazza Gramsci. Trains are slower, about 1 hour 30 minutes, and strikes are common.

Practical tips

Keep the car out of the walled centre of Siena, where cameras fine unauthorised vehicles. Pick up and drop off at a car park outside the walls instead. Prices in this page come from published fare pages and older listings, so confirm before you travel.

Official information: San Gimignano bus line 130 and Monteriggioni access . Tours to compare: Tuscany day trips on GetYourGuide .