Castellina in Chianti, A hidden Gem in the Chianti Region

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 considered 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 just want to drive around the Chianti to enjoy the panoramic views, hilly vineyards, olive groves, and sharp curves, you could include a stop at Castellina in Chianti. It is also very pleasant to explore with a great deal of charm and some interesting monuments.

Typical Tuscany countryside
Typical Tuscany countryside

Via delle Volte

One of the imposing sights is the underground tunnel. The underground tunnel goes around the city, enclosing the city center from below. It is a cool and refreshing place to escape from the summer sun. The tunnel is now called Via della Volte. Via della Volte is a street with vaults along almost its entire length. Along the street there are many shops, artisans and restaurants.

The underground tunnel in Castellina in Chianti
The underground tunnel in Castellina in Chianti

Church of San Salvatore

Walking along the main street you will also pass the Church of San Salvatore. The church actually looks quite 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.

The Church of San Salvatore in Castellina in Chianti
The Church of San Salvatore in Castellina in Chianti

Taste a glass of wine at enoteca

The village’s main activities are around Via Ferruccio which is lined with cafés, shops, restaurants – and enotecaBeing in Chianti you should make sure to stop at a local enoteca (wine bar) and taste the region’s best wines.

Shops sell mainly local products, for example Pasta and cooking utensils 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 tour Chianti Authentic Wine Tasting Experience offers the best values in terms of wine tasting and exploring Chianti region. You will enjoy breathtaking landscapes of vineyards and olive groves, visit cellars, taste the famous wines and typical products. Please check the details here.

Local pasta product, Castellina in Chianti
Local pasta product, Castellina in Chianti

The fortress of Castellina in Chianti

The main fortification is the Rocca Its huge 14th-century tower has a magnificent view over the town and the surrounding hillside. It is a stunning venue for civil wedding ceremonies or events. It is now used by local government and the Archaeology Museum of Chianti Senese.


Museo Archeologico di Chianti Senese

The Archeological Museum of Chianti is inside the fortress. It exhibits important archeological findings from the surroundings that testify the ancient origins of the Chianti region. There are also several exhibits of pieces from neighboring digs.

Kitchen tools made of olive trees
Kitchen tools made of olive wood

Where to stay at Castellina in Chianti

Hotel Palazzo Squarcialupi is a 15th-century building in Castellina in Chianti. It offers a garden with an outdoor swimming pool and a spa. The rooms of Palazzo Squarcialupi feature rustic terracotta floors, exposed wooden beams on the ceilings, and 18th-century furnishings. The bathrooms are in Carrara marble.

In the summertime, you can enjoy the breakfast on the terrace while overlooking the pool and the Chianti Valley. The bus to Siena stops 100m from the hotel which is great if you don’t want to drive there. Please click here to take a look.

Terrace of Hotel Palazzo Squarcialupi, Castellina, Tuscany
Terrace of Hotel Palazzo Squarcialupi, Castellina in Chianti, Tuscany
Rustic sitting corner of Hotel Palazzo Squarcialupi, Castellina, Tuscany
Rustic sitting corner of Hotel Palazzo Squarcialupi, Castellina in Chianti, Tuscany
Breakfast area in Hotel Palazzo Squarcialupi, Castellina, Tuscany
Breakfast area in Hotel Palazzo Squarcialupi, Castellina in Chianti, Tuscany

How to get there

The best way to reach Castellina is by car. Along the Chianti route, there are many beautiful scenes where you can stop to take some memorable photos.

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.

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