Castellina in Chianti is a fortress town that once guarded a frontier. In the Middle Ages, the hills between Florence and Siena were the front line of a long rivalry, and Castellina was on the Florentine side, with a stout castle built to watch the enemy. The fortress, the Rocca, still stands in the centre of the village, and part of it is now a small museum. Nearby is a covered street, the Via delle Volte, which runs under arches along the old walls and feels like a medieval alley, with cool air and stone vaults overhead. The town was one of the three original members of the Chianti League, a military and political alliance of the fourteenth century that gave the region its name.
The history goes back much further than the Middle Ages. Just outside the town is an Etruscan burial mound, a reminder that people were living on these ridges long before Florence or Siena existed. The museum in the Rocca has finds from the area, and the landscape of vines and olives has been farmed for thousands of years. The wine is the heart of the local economy, with Chianti Classico produced by the estates all around.
For a rider, the ride to Castellina is a classic. The Chiantigiana, the state road between Florence and Siena, runs through the town, with easy bends and long views across the vineyards. The surface is generally good and the gradients are gentle, but the road can be busy with traffic, especially at weekends and in high summer, so weekdays are better. On the side roads, you will find narrow lanes and gravel tracks, with farmhouses and cypress avenues. Spring and autumn are the best seasons, with soft light and green or golden hills.
Castellina has several wine shops, cafes and restaurants, and the food is typical of the region, with Tuscan bread, pasta with boar sauce, and grilled meats. It is a good place for a leisurely lunch, with plenty of choice. For fuel, there is a station on the main road in the area, but it is wise to fill in larger towns such as Poggibonsi, about eleven kilometres away, where you will find more services and supermarkets.
On the way south towards Siena, the road passes some of the most beautiful stretches of the Chianti, with the vines in neat rows and the old stone houses sitting in the folds of the hills. Take it slowly and enjoy it.