Castellina in Chianti in Tuscany, A Wine Region in Italy

Castellina in Chianti in Tuscany 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 ArbiaPesa, and Elsa rivers. Therefore, this small town is known as the capital of Chianti.

Castellina in Chianti in Tuscany 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.

Castellina-in-Chianti in Tuscany

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.

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 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.

Narrow streets with shops in Centre in Castellina-in-Chianti in Tuscany, Italay

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 barBeing 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 private Chianti region tour with wine tasting. It offers the best value and the impressive landscape of the Chianti Hills, covered with vineyards and sunflower fields.

Local pasta product, Castellina in Chianti in Tuscany
Centre of Castellina-in-Chianti

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.

Chianti wine route, Tuscany Italay

Travel tips for Castellina in Chianti in Tuscany

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.


  1. Last October I went on the vacation of my dreams. We spent 2.5 weeks in Italy, five were spent in Castellina de Chianti. It was everything I expected of the Tuscan region. The vineyards are beautiful. The wildlife was cool, wild boar and red elk. The town was inviting. We had dinner at the same restaurant 3 times, yes it was that good. Like I said, vacation of a life time. Well, we are starting to plan to go back…

  2. 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.



  3. 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.

  4. 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.

  5. 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!

  6. 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!

  7. 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!

  8. 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 😉

  9. 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.

  10. 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.

  11. 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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