Right in the heart of Tuscany, the beloved town of Castellina in Chianti lies beneath the rust, to be discovered as a diamond. With the thrill that comes with the rolling hills, world-class wine, and not to mention the picturesque streets, Castellina in Chianti is the superior Tuscan experience.

With a population of 2,800 to 2,860 people, Castellina in Chianti has something to offer everyone, whether you are a foodie or a wine enthusiast. Going through the town’s narrow streets, you will indeed have a feel of the Middle Ages, when Castellina played a perfect role in the Siena and Florence wars. You can see from the ancient buildings, churches, fortresses, and towers that stood the test of time and told of its stories.

The town is situated in the Chianti wine region, which is well-known for its Sangiovese-based red wines. You can tour the several wine stores dotted around the town and sample the various Chianti types. We advise you to also visit the cellars and vineyards in the surrounding region of Castellina for a more genuine and profound experience.

Keep reading to explore the beauty and cultural richness of this Tuscan jewel.

How to Get to Castellina in Chianti

Castellina in Chianti, as earlier stated, is indeed a picturesque hilltop town. It is located in the province of Siena, Tuscany, Italy, with an altitude of 375 meters above sea level. The rolling hills of the Chianti Classico wine region surround it. Tourists are sure to be phased by the breathtaking views from the town center and the vibrant atmosphere of its cobblestone streets.

Siena is not that distant from Castellina as it is just 14km in the distance, and it is easier to reach either by public transport or car. This tourist-centered town is an ideal starting point for day trips as it is also not too far off the renowned cities of Florence and San Gimignano.

Read more: Towns in Tuscany – 15 Jewels of Italy’s Rich Culture

5 Things to Do and See in Castellina in Chianti

When you hear about Castellina in Chianti, you should know it is a small town, given its culture and history. Besides all of its cultures and histories, here are some things that you could do to make you feel among in Castellina in Chianti:

1. The City Center

The historic center of the city of Castellina in Chianti
Castellina in Chianti, City Center – “Castellina in Chianti 10” by René Hourdry is licensed under CC BY-SA 4.0.

The city center of Castellina in Chianti is filled with narrow streets, old buildings, and small shops selling local products; it is a must-visit for any visitor to the town. The feeling you get when walking through the city center is heavenly, like stepping back in time to the Middle Ages.

Be sure to stop at the Piazza del Comune, the main square home to the town hall and the clock tower.

2. The “Rocca” Fortress

The "Rocca" fortress in Castellina in Chianti
The “Rocca” fortress in Castellina in Chianti – LigaDue, CC BY-SA 4.0, attraverso Wikimedia Commons

The small hilltop town of Castellina in Chianti is a remarkable place for sightseers and first-timers to taste history. The amazing “Rocca” fortress has stood the test of time since the 11th century, making it one of the popular tourist attractions today.

It was built to act as a protection against regular threats from nearby Florence. Local stones were used for its construction; surprisingly, it still holds the fort today. Inside, visitors can explore the walls, towers, and ramparts which the Republic of Florence originally built. There are also some archaeological findings, including a large tombstone dating back to the Middle Ages.

3. Museo Archeologico del Chianti Senese

An old one horse carriage at the Sienese Chianti archaeological museum, in Castellina in Chianti
Museo Archeologico del Chianti Senese, Castellina in Chainti – “Castellina in Chianti (Si)” by mirella bruni is licensed under CC BY-NC 2.0.

Visitors to Museo Archeologico del Chianti Senese can explore a treasure trove of local Etruscan finds, including the star attraction, an Etruscan chariot from the Montecalvario tumulus tombs nearby from the 7th century. The museum is located in Castellina in Chianti and displays many archaeological and historical findings coming from the Chianti area. 

Visitors can also climb the tower for a beautiful view of Castellina with the Chianti mountains in the distance. A visit to the museum includes exploring the fortress and enjoying a striking view of the town and surrounding mountains.

Read more: Etruscan Cities in Tuscany – Ancient Roads to Temples & Tombs

4. Church of San Salvatore

The Church of San Salvatore in Castellina in Chianti – Vignaccia76, CC BY-SA 3.0, via Wikimedia Commons

Visitors to the Church of San Salvatore can explore Torre Paleologa, Big Bench, Locanda Cafe, Casa Barco, Santuario Della Madonna Del Pozzo, and other attractions in Abbadia San Salvatore. Entry to the Church of San Salvatore is free and visitors can admire its ornate facade.

The Church of San Salvatore, which dates back to the 10th century is one of the most important religious sites in Castellina in Chianti. It features a beautiful Romanesque facade where you will find frescoes dating back to the 14th century, as well as a wooden crucifix from the 13th century.

5. Medieval Tunnel “Via delle Volte”

The mysterious medieval tunnel of "Via delle Volte", in Castellina in Chianti
The mysterious Via delle Volte, in Castellina in Chianti – Sailko, CC BY-SA 4.0, attraverso Wikimedia Commons

Via delle Volte is a medieval tunnel inside the walls of Castellina in Chianti that houses shops, craft shops, and offers a unique stroll in the countryside. Formerly used for defensive purposes, it is now an ideal location for a romantic lunch. The little openings in the wall provide beautiful views of the surrounding landscape.

Wine Tasting in Castellina and in the Chianti Hills

Tuscany is one of the most famous Italian regions for its wine production. The Chianti region, together with Bolgheri, Montalcino, Scansano, Montepulciano, San Gimignano, is one of those places that cannot be missed on the map of wine lovers. In this sense, Castellina in Chianti and its countryside have a lot to offer.

It might be a dream come true if you are looking to try out the best Tuscan wines. You won’t want to miss the Cantina Antinori at Tignanello, founded in 1480. Cantina Antinori is one of the oldest and most verified wineries in the region. You can get up close and personal with the wines as they offer tours of their vineyards and wineries.

Villa Vignamaggio is another popular spot well known for its outstanding wines. Known to be in business for over 600 years, this can be a perfect spot for tasting some delicious Chianti wines.

Castellina is truly the home to many wine bars and restaurants where you can easily taste some perfectly made local wines. La Cantina di San Giovanni is a favorite among locals and travelers alike as it is located right in the center of town. They have a wide preference for wines by the glass and delicious plates of charcuterie and cheese to go with it.

Best Places to Stay in Castellina in Chianti

A beautiful agriturism to stay in Castellina in Chianti
Agriturism in Castellina in Chianti – “Toscana, Agriturismo Rocca di Cispiano, Castellina in Chianti (Siena)” by Toprural is licensed under CC BY-SA 2.0.

Castellina in Chianti is a charming town located in the heart of Tuscany, offering visitors an authentic Italian experience. To fully immerse yourself in the local culture, choosing the right accommodation is essential. Here are some of the best places to stay in Castellina in Chianti:

Hotel Palazzo Squarcialupi

Inside the private hot tub in Hotel Palazzo Squarcialupi

This elegant hotel is located in a beautifully restored 15th-century palace in the heart of Castellina in Chianti. It offers spacious and luxurious rooms with antique furnishings and modern amenities. Guests can enjoy a delicious breakfast buffet each morning, and the hotel’s on-site restaurant serves traditional Tuscan cuisine.

Location: Via Ferruccio 22, 53011 Castellina in Chianti, Italy

Stars: 4

Features: Outdoor swimming pool, Spa and wellness centre, Tea/coffee maker in all rooms

Reviews: 9.1/10

Villa Casalecchi

Aerial view of the Hotel Villa Casalecchi with outdoor pool
Photo Credit: Booking.com – Hotel Villa Casalecchi

This charming bed and breakfast is located in a renovated farmhouse surrounded by vineyards and olive groves. It offers comfortable rooms with rustic decor and stunning views of the surrounding countryside. Guests can relax in the outdoor pool or the beautiful garden and enjoy a delicious breakfast made with local ingredients.

Location: Casalecchi 18 – Strada del Mandorlo, 53011 Castellina in Chianti, Italy

Stars: 4

Features: Outdoor swimming pool, Good breakfast, Bar

Reviews: 8.4/10

Castello di Fonterutoli

Aesthetic and beautiful room in Castello di Fonterutoli Wine Resort
Photo Credit: Booking.com – Castello di Fonterutoli Wine Resort

This historic castle offers luxurious accommodation in an idyllic setting surrounded by vineyards and olive groves. It features spacious rooms with elegant decor and modern amenities, as well as a gourmet restaurant serving traditional Tuscan cuisine. Guests can enjoy wine tastings and tours of the castle’s wine cellars and relax by the outdoor pool or in the beautiful garden.

Location: Via Puccini 4, 53011 Castellina in Chianti, Italy 

Stars: 4

Features: Free parking, Restaurant, Bar

Reviews: 8.8/10

Explore more: Gaiole in Chianti – The Heart of the Tuscan Wine Region

The Best Restaurants in Castellina in Chianti

A grocery store and restaurant in Castellina
A grocery store in Castellina in Chianti that also offers food service

Castellina in Chianti is renowned for its traditional Tuscan cuisine, made with fresh, locally sourced ingredients. From fine dining restaurants to cozy trattorias, there are plenty of options to satisfy your appetite. Here are some of the best restaurants in Castellina in Chianti.

Trattoria La Torre 

Tagliatelle with Porcini mushrooms cooked by the
Photo Credit: anticatrattorialatorre

The restaurant boasts a magnificent view of the town center and a terrific atmosphere. Trattoria La Torre has a large menu that includes appetizers cooked from their own cold cuts, handmade pasta dishes like Taglierini al tartufo nero, and exquisite gastronomy. The wine suggested has been purposefully chosen from the Chianti Classico region to deepen the connection between wine, food, and local geography.

Official Website: Trattoria La Torre

Location: Via Salicotto, 7, 53100 Siena SI

Reviews: 4.2/5

Insider Tip: Delicious Pici

Osteria Le Cantine 

Le Cantine provides a wonderful setting in which to savor Chianti wine by the glass or bottle. The wine bar offers an amazing range of Chianti wines from leading wineries in the area, as well as light meals like bruschetta and panini.

Osteria Le Cantine is a notable restaurant that specializes in traditional Tuscan food coupled with superb Chianti wines for a more premium dining experience. The wine selection at the restaurant is vast, with a concentration on Chianti Classico wines from the region’s best producers.

Read more: Tuscan Food – A Wealth of Pasta Sauces, Soups, and Sweets!

Ristorante Albergaccio 

Delicious dish with 𝙸𝚕 𝙲𝚊𝚟𝚘𝚕𝚘 𝚗𝚎𝚛𝚘 served by the Ristorante Albergaccio 
Photo Credit: Ristorante Albergaccio 

Restaurant Albergaccio is one of the top restaurants in Castellina owing to its rustic yet fashionable establishment in wood and stone, Tuscan cuisine that tends toward inventive dishes without sacrificing regional tastes, and its rustic but stylish institution in wood and stone. It is built in an antique farm structure and is located in one of Castellina in Chianti’s most picturesque panoramic regions.

The restaurant serves Tuscan food that is inventive without sacrificing regional tastes. The restaurant also has an impressive wine list, featuring some of the best wines from Tuscany and beyond.

Official Website: Ristorante Albergaccio 

Location: Via Fiorentina, 63, 53011 Castellina in Chianti SI

Reviews: 4.5/5

Insider Tip: Exquisite local cuisine

The Best Attractions around Castellina in Chianti Italy

The typical wines of castellina in chianti displayed on a shelf
Chianti wine produced in Castellina

Castellina in Chianti is a nice place for checking out a lot of attractive centers in its surrounding area. Here are six of the best attractions to visit, from charming medieval towns to breathtaking countryside vistas:

San Gimignano

San Gimignano is a UNESCO World Heritage site and it is one of the most scenic towns in Tuscany. It is a Tuscan hill village southwest of Florence surrounded by 13th-century fortifications. Tourists may visit the Archeological Museum, Crystal Glass Museum, Civic and Diocesan Museum, and, if time allows, the market with local items on the first Sunday of each month. San Gimignano is often known as “Medieval Manhattan” in Italy because of the many towers that still survive today.

Greve in Chianti

The Chianti hills countryside, around Castellina
The Chianti hills countryside, around Castellina

Greve in Chianti is located in the heart of the Chianti wine region and, as such, is known for its wine festivals and markets. This charming town is the perfect spot to taste the local wine and food. You can visit to the historic square, Piazza Matteotti, and the Church of Santa Croce. Or just take a stroll through its picturesque streets.

Radda in Chianti

The town’s tumultuous history may be seen on the main plaza. The majestic Palace dei Podestà may be found here, as shown by the array of coats of arms on the exterior. ‘Podestà’ was the main magistrate, local authority, and leader of the Chianti League. Each new podestà would add his family emblem to those who had gone before him.

A short stroll will enable you to view the whole town, which has a classic Medieval layout. The delightful ambiance is created by the walls, the charming squares, and the beautifully renovated ancient residences. Radda is an excellent choice for anyone seeking peace and quiet. There are charming stores and wine bars where you may sample the local Chianti wine.


Certaldo is a medieval town located in the heart of the Valdelsa region. Known for its beautiful architecture and cultural heritage, Certaldo is the birthplace of Giovanni Boccaccio, the author of the Decameron. You can visit his house and museum and explore the town’s historic center, which includes the Palazzo Pretorio and the Church of Saints Tommaso and Prospero.


Elsa river, along the SentierElsa trail
Elsa river, along the SentierElsa trail – Photo by Alessio Pellegrini CC BY-NC-SA 2.0

The SentierElsa is a picturesque trail that winds its way through the beautiful countryside of the Val d’Elsa. Along the way, you can visit the village of Colle di Val d’Elsa and explore the Elsa River.


Monteriggioni can be viewed in one hour or less, but its beauty and enjoyable activities warrant at least a couple of hours of your time.  You’ll want to soak it all in and picture yourself living in the Medieval Ages. It’s a great day excursion from Florence, Siena, or wherever in the Tuscan countryside. 

You can also stay the night in town (or nearby), but I don’t believe you’d need more than one night to see all Monteriggioni has to offer. I recommend exploring the town’s narrow streets and visiting its landmarks, such as the Church of Santa Maria Assunta and the Museum of Monteriggioni.

You might look at the Middle Ages and Renaissance armor and weaponry reproductions. This little museum will appeal to both children and adults. There are comprehensive miniature representations of wars, military history, and castle life in addition to the armor.

FAQ: Where Is the Tourist Office?

A panoramic view of the countryside around Castellina
A panoramic view of the countryside around Castellina

The tourist office in Castellina in Chianti is at Via Ferruccio, 40, Castellina in Chianti.

At the tourist office, you can obtain information about the town and its surroundings, including maps, brochures, and advice on things to do and see. The office is typically open during normal business hours, but it’s always best to email (ufficioturistico [at] comune.castellina.si.it) or check their official website to confirm the opening times.

Also, there are several guided tours available in and around Castellina in Chianti, many of which are provided by private operators. An opportunity to enrich your experience and provide you with valuable information on the history, culture, food, and wines of Chianti.