Along One of Chianti's Prettiest Roads
The Via Cassia (SR2) between San Casciano and Bargino, passes the ancient Castle of Bibbione, once residence of the Buondelmonte family, who owned much of this territory in the days when they were throwing fat on the Guelph and Ghibelline fires in Florence. Near Bargino, in the same bellicose spirit, is the impressive fortified hamlet of Montefiridolfi, just east of the Via Cassia.
This road, meanwhile, rolls south through lovely hills towards Tavarnelle Val di Pesa, of mostly 19th-century origin, and medieval Barberino Val d’Elsa, with some Etruscan finds in the town hall and a good 10th-century Romanesque church, the Pieve di Sant’Appiano.
From here the Via Cassia continues to Poggibonsi, with a possible detour to La Paneretta, a sturdy 15th-century fort amid the olive groves, with Baroque frescoes inside.