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Tuscany by car: a 5-day road trip through the hill towns

Tuscany is the easiest great road trip in Italy: short distances, roads that wander, and a town with a square and a restaurant every twenty minutes. Five days is enough.

Published 6 October 2026 · facts fetched from Wikipedia on 6 October 2026

Plan this trip

  1. 1 Florence

    Florence
    Photo by Giorgio Galeotti, CC BY 4.0, via Wikimedia Commons.

    Florence is the capital and most populous city of the Italian region of Tuscany, and, as of 2026, with a population of 361,625, the 8th most populous city in the country. Wikipedia

    Start here, but leave the car outside the centre: the ZTL cameras fine every visitor who drives in.

    Written about in 182 languagesStart a trip here

  2. 2 Chianti and the SR222

    Chianti and the SR222
    Photo by Francesco Sgroi, CC BY 2.0, via Wikimedia Commons.

    Chianti is an Italian red wine produced in the Chianti region of central Tuscany, principally from the Sangiovese grape. It was historically associated with a squat bottle enclosed in a straw basket, called a fiasco. Wikipedia

    Day one: the Chiantigiana south through Greve and Castellina, with a winery stop.

    Written about in 35 languagesStart a trip here

  3. 3 Siena

    Siena
    Photo by Zairon, CC BY 4.0, via Wikimedia Commons.

    Siena is a city in the region of Tuscany in central Italy, and the capital of the province of Siena. With a population of 53,180, it is the 12th-largest city in the region. Wikipedia

    Day two: the Campo, the cathedral, and a night in the old town.

    Written about in 110 languagesStart a trip here

  4. 4 San Gimignano

    San Gimignano
    Photo by Chensiyuan, CC BY-SA 4.0, via Wikimedia Commons.

    San Gimignano is a small walled medieval hill town in the province of Siena, Tuscany, north-central Italy. Wikipedia

    Day three: the towers, best before ten in the morning. Then Volterra.

    Written about in 83 languagesStart a trip here

  5. 5 Val d'Orcia

    Val d'Orcia
    Photo by Carlo cattaneo fotografie, CC BY-SA 4.0, via Wikimedia Commons.

    The Val d'Orcia or Valdorcia is a region of Tuscany, Central Italy, which extends from the hills south of Siena to Monte Amiata, between the provinces of Siena and Grosseto. Wikipedia

    Day four: the cypress roads of the postcards, Pienza and Montalcino.

    Written about in 41 languagesStart a trip here

  6. 6 Montepulciano

    Montepulciano
    Photo by Chensiyuan, CC BY-SA 4.0, via Wikimedia Commons.

    Montepulciano is a medieval and Renaissance hill town and comune in the Italian province of Siena in southern Tuscany. Wikipedia

    Day five: the wine town on the hill, and the thermal baths at Bagno Vignoni on the way back.

    Written about in 60 languagesStart a trip here

Riding or driving it

This is a 400 km trip in five days. Give Roadlegs a short day, 100 km and 3 hours, and an hour at each stop, and it leaves room for lunch.

Open the plan in Roadlegs How the planner handles this vehicle.

About the facts and photos

The descriptions in italics are the opening sentences of the Wikipedia article for each place, used under CC BY-SA 4.0, fetched on 6 October 2026. Photos are from Wikimedia Commons under the licence named beside each one. "Written about in N languages" counts the Wikipedia editions that have an article, from Wikidata; it is a measure of how well known a place is, not a rating. Everything else is the author's own opinion. Roads close with the seasons: check before you go.

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