Castellina in Chianti, A hidden Gem in the Chianti Region

Typical Tuscany countryside
Typical Tuscany countryside

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

One of the impressive sights is the underground tunnel. The underground tunnel 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 street, there are many shops, artisans and restaurants.

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

Church of San Salvatore

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

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 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 tour Chianti Authentic Wine Tasting Experience offers the best value including wine tasting and exploring Chianti region. You will enjoy the breathtaking landscapes of vineyards and olive groves, visit cellars, taste the famous wines and typical products. For further detail please check the details of the tour Chianti Authentic Wine Tasting Experience.

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.

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.

Castellina in Chianti, Tuscany


  1. Chianti is such a beautiful place, I’ve been here last year in spring. A place that I would not get tired of seeing over and over, love the Tuscany area.
    The tunnel is amazing, the surrounding towns are very interesting. Love the food as well.
    I I will not get tired of going back here even every year.
    Ciao Bella

    1. Hi Bella,

      Thanks for reading!
      We stayed there too short and hopefully to stay there a few nights next time. It deserves more attention indeed.



  2. An underground tunnel that goes around the town? How cool is that! Castellina sounds like a great little village in the Chianti region and I would love to visit the fortress of Castellina, given my love for royal and majestic places. I’d want to rent a car and drive there from Florence, with a fantastic view of the vineyards.

  3. This sounds like heaven – the old world charm, calm lifestyle, delicious food and wine! I could spend a week just enjoying the views and architecture. My husband and I are history buffs so we would love to see the fortress and the Archeological Museum of Chiant.

  4. This sounds like the DREAM! The food, the wine ugh… take me there now! I’ve never been to Chianti but I really love the small, local towns of Italy. There’s something so special and homey about them. The olive wood kitchen tools are beautiful! And those gorgeous pastas? I would totally bring some back with me haha!

  5. That vineyard looks like a dream! How I wish to teleport now to Chianti and explore this beauty. And also the idea of waking everyday with that view at Hotel Palazzo Squarcialupi is absolutely a fabulous dream!

  6. The country-side of Florence is just so pure, green and serene isn’t it!
    Underground tunnel, filled with shops that have outdoor seating arrangements? Wow! That’s super cool.
    As a wine lover, I’d definitely want to go on that wine-tasting experience.
    I’ve seen these kitchen equipment made of olive wood in Greece too. I wanted to buy them, but my flight luggage allowance didn’t allow that! Esp., the honey spoon was something I really wanted to buy!

  7. I visited Castellina in Chianti a couple of years ago and I agree with you, it’s super pretty! Via delle Volte was perhaps my favorite part of the town, such a unique street right? The Hotel Palazzo Squarcialupi looks fantastic, I need to take note of this for the next trip 😉

  8. This looks like the beautiful Italian countryside I remember driving through. Those Chianti region vineyards are some of the most picturesque I’ve ever seen. The underground tunnel is very neat thanks for writing about it. I would also like to visit the fortress and the Palazzo Squarcialupi hotel looks amazing.

  9. One reason why I wish to visit Europe and yes including Tuscany is because I want to experience their wine culture. I love wine, and I am always curious about it’s production.

  10. I love everything included in this post — old architecture, wine-tasting, and pasta. I wonder how it’s like living here? This place is definitely for me — slow and quiet.

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