Chianti road: Florence to San Gimignano and Volterra

Route description

Leave Florence south on the SR222, the Chiantigiana, which winds through vineyards and olive groves all the way to Siena. After about 30 km you reach Greve in Chianti, whose funnel-shaped arcaded square is the market place of the region. Walk or drive the short lane up to Montefioralle, a ring of stone houses above the town, before continuing west on minor roads to the abbey of Badia a Passignano.

Back on the SR222, Panzano and Castellina sit on ridges with wide views over the vines; Radda, a short detour east on the SR429, was the old capital of the Chianti League. Wine tasting is everywhere, but the driver should go easy: Italian police do check. The roads are narrow and twisting, fine for vans but slow for large motorhomes, especially behind tractors at harvest time in September and October.

South of Castellina the landscape opens towards Siena. Leave the SR222 for Monteriggioni, a complete circle of walls and towers on a low hill beside the Florence–Siena highway. From there, secondary roads through Colle di Val d’Elsa bring you to San Gimignano, where 14 medieval towers survive. The centre is closed to traffic; use the numbered car parks outside the gates and come in the evening, after the day coaches leave.

The last leg, about 30 km partly on the SR68, climbs to Volterra, an Etruscan and medieval town on a high ridge above eroded clay slopes. See the Roman theatre from the road along the walls, the Etruscan gate and the alabaster workshops. Spring and autumn are the best seasons; in summer, start early. Allow at least three days to drive this route without rushing, with nights in Greve and San Gimignano.