As you follow the scenic via Chiantigiana from Greve in Chianti southwards, the road winds upwards from the Val di Greve towards Panzano from which it more or less follows the ridges until you arrive at the little town of Castellina in Chianti.
The area around Castellina is very popular with visitors staying at agriturismi (farmhouse vacation rentals) because it is within easy reach of Sienna while remaining a very beautiful example of the Chianti countryside. The picturesque villages in the Colline del Chianti to the east are also within easy reach by car – Volpaia, Gaiole in Chianti, Radda in Chianti and Castelnuovo Berardenga, for example.
The main street of Castellina is limited to pedestrians and is well-provided with cafes, restaurants, groceries and fruit and vegetable shops. Castellina also has an incredibly good gelato shop on the corner where the main road heads for Greve.
While definitely a good place for R&R, Castellina has a small but good museum housing some local Etruscan antiquities among other things, a quite unusual covered or vaulted street under the fortifications, and a major Etruscan tomb nearby.
Castellina Chianti Wine Festival
A wine festival takes place in Castellina every Pentecost Sunday and the preceding Friday and Saturday, with wine tasting stalls being set up in the vaulted street under the town wall. As with the wines fairs in Panzano and Greve, you buy a glass from the Secretariat and are then able to taste a certain number of wines for free. The glass cost 10 euros, last time I was there. There are usually around 20-50 exhibitors, each with between 3 and 6 wines. Some of these producers will ship cases of wine, if you find one that you really like.
Castellina in Chianti is easily reached from Sienna by comfortable SITA bus, but there is no connection to Florence by bus, so a car is recommended for visitors staying in this area.
Things to see in Castellina in Chianti.