Cycling from San Casciano Val di Pesa to Greve in Chianti
The 100-kilometer tour starts in San Casciano Val di Pesa and passes through Barberino Tavarnelle, Castellina in Chianti and Greve in Chianti, allowing you to admire some of the area’s most iconic views of vineyards, villages and castles.
You can ride along it on a road bike and, if you want to enjoy it to the full, we suggest splitting it into 2 stages, with an overnight stay in Panzano, in the municipality of Greve in Chianti.
Setting off from Il Poggione Park in San Casciano Val di Pesa and alongside the medieval walls, you leave the town and tackle the uphill and downhill stretches between the villages of San Pancrazio and Fornacette. You then climb to Lucardo and San Donato in Poggio. The latter is considered one of the Most Beautiful Villages in Italy (I Borghi più belli d'Italia). Then there are the villages of Fiano and Marcialla before arriving in Tavarnelle Val di Pesa.
From here, a more challenging section begins, along the secondary road through vineyards and woods, to the village of Tignano with its castle. When you reach provincial road SP101, you will start to climb along the spectacular road that leads to Castellina in Chianti. You can stop here and enjoy a visit to the historic center with the charming Via delle Volte, an ancient covered walkway designed by Filippo Brunelleschi.
From Castellina in Chianti, regional road SR222 descends through vineyards and dreamy landscapes, to the small village of Panzano, an ideal place to stop along the loop road: you might want to stay for a few hours or spend the night here and leave, feeling rested, the next day. In any case, take the opportunity to taste some typical dishes like the famous "ciccia" (meat), accompanied by a nice glass of Chianti Classico wine.
From Panzano, follow regional road SR22 to Greve in Chianti. Here, you can admire the famous Piazza Mercatale with its statue of the explorer Giovanni da Verrazzano, who was born in the nearby castle of the same name. While cycling up and down hills with views of the vineyards, you will come across the villages of Chiocchio, Strada in Chianti and Santa Cristina.
After crossing the municipality of Impruneta, you will reach Chiesanova, famous for its delicious schiacciata flatbread, and then Cerbaia, where you will begin the last 4 challenging uphill kilometers, taking you back to San Casciano Val di Pesa.