Castellina in Chianti is one of the most important ancient towns between Florence and Siena. It is in the heart of Chianti vineyards and between the valleys of the Arbia, Pesa, and Elsa rivers. Therefore, this small town is known as the capital of Chianti.
Castellina in Chianti is actually on the SR222, the so-called Strada Chiantigiana, which is the main tourist route through the Chianti region. You can combine with the visiting of Siena or the hilltop village Monteriggioni as we did. Or, if you want to drive around the Chianti to enjoy the panoramic views, rolling vineyards, olive groves, and sharp curves, you could include a stop at Castellina in Chianti. It is pleasant to explore with a great deal of charm and some interesting sites.
Via Delle Volte, an underground tunnel
One of the impressive sights is the underground tunnel. It goes around the town, enclosing the town center from below. It is a cool and refreshing place to escape from the summer sun. The tunnel is now the street Via Della Volte, with vaults along almost its entire length. Along the tunnel, there are many shops, artisans, and restaurants.
Church of San Salvatore
Walking along the main street, you will also pass the Church of San Salvatore. The church looks pretty new because it was damaged during the Second World War and was rebuilt. Inside the church, there is a 15th-century fresco of the Virgin and Child by Lorenzo Bicci.
Taste a glass of Chianti wine at an enoteca
The village’s main activities are around Via Ferruccio, lined with cafés, shops, restaurants, and wine bar. Being in Chianti, you should make sure to stop at a local enoteca (wine bar) and sample the region’s best wines. Shops sell mainly local products, for example, Pasta and cooking appliances made of solid olive wood such as Wooden Cheese Tray.
There are also organized tours to surrounding vineyards & small towns with a professional tour guide. The Chianti Authentic Wine Tasting Experience tour offers the best value, including wine tasting and exploring the Chianti region. You will enjoy the breathtaking landscapes of vineyards and olive groves, visit cellars, taste the famous wines and typical products.
The fortress of Castellina in Chianti
The main fortification is the Rocca, whose 14th-century tower has a magnificent view over the town and the surrounding hillside. Rocca is a stunning venue for civil wedding ceremonies or events. Now the local government uses it for the office and is also the Archaeology Museum of Chianti Senese.
Museo Archeologico di Chianti Senese
The Archeological Museum of Chianti is inside the fortress. It exhibits significant archeological findings from the surroundings that testify to the ancient origins of the Chianti region. There are also several exhibits of pieces from neighboring digs.
Travel tips for Castellina in Chianti
Where to stay
How to get there
The best way to reach Castellina is by car. If you come from Florence, you should take the main highway Florence-Siena and exit at San Donato in Poggio. Then follow the SP101, which will turn into the SP76, which leads to Castellina in Chianti.
But if you come from Siena, you should take the main highway Siena-Florence and exit at Badesse. Then follow the SP 119 until it turns into the SR222 (Chiantigiana), which leads to Castellina in Chianti.
You can also join an organized tour to explore Castellina in Chianti.