Tuscany hill towns road trip: Siena, San Gimignano and Val d'Orcia

Southern Tuscany is made for a slow drive: medieval squares on hilltops, roads lined with cypress trees, and vineyards rolling away in every direction. The hill towns are close together but poorly served by public transport, so a car gives you the freedom to stop wherever the view opens up. Base yourself in Siena and spend two or three days exploring. Here's how to plan it.

The route at a glance

• Siena: your base. Allow at least a full day on foot.
• San Gimignano: roughly an hour's drive north-west of Siena. Half a day.
• Val d'Orcia: about an hour south of Siena. A full day for the valley, Pienza and Montepulciano together.
• Pienza: in the heart of the Val d'Orcia. Two or three hours.
• Montepulciano: a short drive east of Pienza. Half a day, or an evening.

Driving times are approximate and country roads are slower than they look on a map.

Siena

Start in Siena's Piazza del Campo, the sloping, shell-shaped square where the Palio horse race is run twice each summer, in early July and mid-August. The Torre del Mangia rises from the town hall on one side; its climb is steep but the view over the rooftops is superb.

Then walk up to the cathedral, striped in black and white marble, with an inlaid marble floor, a richly frescoed library and a view from the unfinished façade of the planned larger cathedral. Tickets for the cathedral complex and the tower are sold separately, and slots can fill in summer.

Siena's historic centre is car-free for visitors, so leave the car at your hotel or in one of the car parks outside the walls; several have escalators up into town.

San Gimignano

North-west of Siena, San Gimignano rises above the vineyards with more than a dozen medieval stone towers, survivors of the many built by rival families. Walk between its two main squares, climb the tallest tower for the view, and try the local white wine, Vernaccia di San Gimignano.

It's one of the busiest small towns in Tuscany, so arrive early or late in the day, when the tour buses have gone. On the way, the walled hamlet of Monteriggioni is a short detour just off the main road.

The Val d'Orcia

South of Siena lies the Val d'Orcia, a UNESCO World Heritage landscape of gentle hills, farmhouses and lines of cypress trees, shaped by Renaissance ideas of how an ideal countryside should look. Drive it slowly: the roads between San Quirico d'Orcia, Pienza and Montalcino are the classic stretches, and the famous cypress avenues are along or just off them.

Pull over only where there's a proper lay-by. Many of the best-known viewpoints are on private farm tracks, so photograph from the road rather than driving onto them.

Pienza

Pienza was rebuilt in the 15th century as an ideal Renaissance town by Pope Pius II, who was born here. Its small central square, with the cathedral and the papal palace, was planned as a single composition. Walk along its walls at sunset, when the whole valley glows below, and try the local pecorino cheese, sold in shops all over town.

Montepulciano

Finish in Montepulciano, a long hilltop town famous for its Vino Nobile red wine. Climb its steep main street, the Corso, past palaces and cellar doors to the Piazza Grande at the top. Many wine cellars run tastings; the driver should stick to a sip or skip it, as Italy's drink-driving limit is low. Just below the town, the Renaissance church of San Biagio stands alone in a meadow.

Nearby alternatives

• Montalcino: a fortified hill town known for Brunello wine, on the western edge of the Val d'Orcia.
• Bagno Vignoni: a tiny village whose main square is a pool of thermal water.
• Chianti: the wine hills between Siena and Florence, an easy way to drive between the two cities.

Driving tips

• Traffic zones: most historic centres are limited traffic zones (ZTL), and cameras fine cars that enter without a permit, often months later via the rental company. Park outside the walls and walk in. If your hotel is inside a zone, ask whether it can register your number plate. Check the current rules for each town before you go.
• Parking: use the signed car parks outside the walls, and keep coins or a parking app ready. Blue lines usually mean paid parking and white lines free, but check the signs.
• Licence: drivers from outside the EU may need an International Driving Permit alongside their licence. Check the current requirements.
• Roads: narrow and winding, with the occasional gravel stretch. A smaller car is easier to park.

When to go and practical tips

Spring and autumn bring the best light, fewer crowds and, from around September into October, the grape harvest. Summer is hot and busy, and Siena is extremely crowded on Palio days. Winter is quiet, with some hotels and restaurants closed.

• Where to stay: Siena makes the most practical base, or split your nights between Siena and a farm stay (agriturismo) in the Val d'Orcia.
• Arriving: most visitors fly into Florence or Pisa and pick up a car there. If you're spending time in Florence first, see our guide on where to stay in Florence and collect the car on the day you leave.
• Book ahead for agriturismi and Siena hotels in May, June, September and October.

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Cover photo: kuhnmi, CC BY 2.0, via Wikimedia Commons