Tuscany by car: Pisa, Florence, San Gimignano, Siena and Val d'Orcia

Tuscany by car comes down to five stops running from west to south: Pisa, Florence, San Gimignano, Siena and Val d'Orcia. Each has its own colour — white marble, a red dome, stone towers, reddish brick and finally golden hills — so the route reads as one long, slow shift from marble to clay.

The drive starts in the west, at Pisa, because it is closest to the sea and because it is easiest to leave once you have seen the tower. The Piazza dei Miracoli is a broad, grassy expanse on which the cathedral, baptistery, Camposanto and Leaning Tower stand as if cut from one white marble block. The tower was begun in 1173 and began to lean while it was still rising, so the upper storeys were built with a corrected angle. The square has been on the UNESCO list since 1987. The climb costs €20 and runs on timed entry, while the cathedral beside it is cheaper at €5. Behind the square waits Piazza dei Cavalieri, the square of the knightly order, within walking distance.

1 dayWhat fits into Pisa before the road to Florence:Pisa in 1 day →

From Pisa the road runs east to Florence, which is recognisable from afar by its red dome above the rooftops. Brunelleschi's dome was completed in 1436 and is covered in red tiles, so from a distance it looks like a coal still glowing over the city. The historic centre was inscribed in 1982 and is restricted for cars; the same rules apply in the centres of every city on this route: ZTL zones in city centres, cameras, fines by post. So the car stays in a garage on the edge, and Florence is seen on foot, across the Ponte Vecchio and from the far bank.

The Uffizi costs €25 on the day and is closed on Mondays, which matters when the route is planned by days. For sunset there is Piazzale Michelangelo, a free viewpoint from which the Duomo looks like the best postcard in this part of Tuscany.

Day tripsWhen Florence becomes the base for the rest of Tuscany:Day trips from Florence →

From Florence the road heads south, towards a hill on which a forest of stone towers is visible from far off. Of the towers once raised by rich families in rivalry, fourteen remain. UNESCO inscribed the historic centre in 1990. On Piazza della Cisterna, paved in brick and ringed by stone palaces, the day's high points are the Torre Grossa (€10) and the Collegiata with its fourteenth-century frescoes (€5). With lunch comes Vernaccia, the wine that in 1966 became the first Italian one with DOC status.

1 dayHalf a day among the towers, hour by hour:San Gimignano in 1 day →

From San Gimignano the road goes on to Siena, a city in which everything unfolds around a single square. Piazza del Campo is a sloping, reddish shell of brick, divided into nine sections, and it is the place every street descends towards. Above it stands the Torre del Mangia, built in the fourteenth century, which climbs for €10. The cathedral is all white and dark marble, and in the periods when its marble floor is uncovered (from 27 June to 31 July and from 18 August to 15 November) the OPA pass is worth the money. The historic centre has been on the UNESCO list since 1995, and twice a year, on 2 July and 16 August, the Palio is run on the Campo.

When to goWhen Siena is easiest to visit:The best time to visit Siena →

After four towns, the last stop needs only a driver. The valley has been under UNESCO protection since 2004 as a cultural landscape, and the only real way to cover it is by car; public transport here follows none of the roads people come for. A small car rents for €26–32 a day, and San Quirico d'Orcia is the place to sleep. From there the SP146 runs to Pienza, with stops wherever a verge allows, and the day closes in Montalcino, whose Brunello was among the first wines with DOCG status in 1980, or at the Romanesque abbey of Sant'Antimo, built of travertine and alabaster and free to enter.

Getting aroundHow the valley is driven, stretch by stretch:Getting around Val d'Orcia →