Sipping and Sightseeing: Castellina in Chianti, Tuscany

Castellina in Chianti in Tuscany is a significant historic town bridging Florence and Siena. Surrounded by Chianti vineyards and embraced by the Arbia, Pesa, and Elsa rivers, it’s rightly hailed as the Chianti capital.

Positioned along the SR222, or Strada Chiantigiana, Castellina is a vital stop on the Chianti region’s tourist trail. Consider combining your visit with a trip to Siena or Monteriggioni, as we did. Alternatively, take a scenic drive through Chianti’s breathtaking landscapes, with Castellina offering a charming pause amidst vineyards, olive groves, and winding roads.

Castellina-in-Chianti in Tuscany
The underground tunnel in Castellina in Chianti

Via Delle Volte, an underground tunnel

One of the most striking sights is the underground tunnel, encircling the town from below like a hidden labyrinth. It offers a refreshing retreat from the summer heat. The tunnel is now transformed into Via Della Volte, lined with charming shops, artisans, and eateries.

Church of San Salvatore

As we walked down the main street, we came across the Church of San Salvatore. Despite its new appearance, it was actually reconstructed after damage during World War II. Stepped inside to admire the 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 centred around Via Ferruccio, lining with charming cafés, shops, restaurants, and a wine bar. We stopped in the local enoteca and sampled the region’s finest wines. Shops predominantly feature local products, including pasta and cooking utensils crafted from solid olive wood, such as the Wooden Cheese Tray.

Additionally, organised tours to surrounding vineyards and small towns are available, led by professional guides. Consider the private Chianti region tour with wine tasting for the best value, offering breathtaking views of the Chianti Hills adorned with vineyards and sunflower fields.

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

The fortress of Castellina in Chianti

The main fortification, the Rocca, has a 14th-century tower offering breathtaking views of the town and surrounding hillsides. It served as a picturesque venue for civil wedding ceremonies and events. Presently, it’s utilised by the local government as an office and houses the Archaeology Museum of Chianti Senese.

Museo Archeologico di Chianti Senese

The Archeological Museum of Chianti is inside the fortress. It showcases significant archeological findings from the surroundings that testify to the ancient origins of the Chianti region. Numerous exhibits displayed artefacts from nearby excavations, providing insights into the region’s history.

Centre of Castellina-in-Chianti
Chianti wine route, Tuscany Italay

Travel tips for Castellina in Chianti in Tuscany

Where to stay

Hotel Palazzo Squarcialupi, in the heart of the town, offers a unique blend of convenience and luxury. Guests can easily explore the charming surroundings. Moreover, the hotel features a spa function, providing guests with a retreat after a day of sightseeing.

How to get there

The best way to reach Castellina is by car. If you’re coming from Florence, take the main Florence-Siena highway and exit at San Donato in Poggio. Follow the SP101, which becomes the SP76, leading directly to Castellina in Chianti.

Alternatively, if you’re coming from Siena, take the main Siena-Florence highway and exit at Badesse. Then follow the SP 119 until it becomes the SR222 (Chiantigiana), which also leads to Castellina in Chianti.

You can also join an an organized tour to explore Castellina in Chianti.

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  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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