Castellina in Chianti

Set on the scenic Chiantigiana, amidst the captivating landscapes of the Chianti, Castellina stands as a quintessential hilltop village adorned with a rich tapestry of history and natural splendour. Renowned for its exquisite wineries, Castellina in Chianti invites visitors to explore its scenic vineyards and woodland treasures. 

From its origins as a strategic Florentine stronghold to its pivotal role in the Chianti League of the 13th century, Castellina exudes a timeless charm steeped in history. Today, amidst its ancient fortifications, Castellina looks much as it did in the 15th century. Visitors can discover La Rocca, now transformed into the town hall and housing a captivating archaeological museum with tempting wine shops nearby. Wander through the labyrinthine streets, where glimpses of the Chianti hills await at every turn.  

If you are looking to base yourself in the heart of the Chianti, with easy access to a plethora of restaurants, attractions and famous towns and cities, explore our collection of villas near Castellina.

Whether you're drawn to the town's historic allure, the promise of culinary delights, or simply to immerse yourself in the beauty of its landscapes, Castellina offers an unforgettable journey through time. Our travel guide brings you all the best things to see and do all in one place.

When visiting Castellina in Chianti, a walk-through Via delle Volte, a covered walkway taking visitors on a walk back in time, is not to be missed. The walkway's construction was part of the fortification of Castellina by Filippo Brunelleschi to resist gunpowder explosions. Today, taverns line Via delle Volte providing scents of culinary tradition whilst the slits in the wall open onto panoramic views of the Chianti.

Web: https://www.visitchianti.net/via-delle-volte-una-splendida-via-di-difesa/

Castellina's historic centre is home to the ancient Rocca di Castellina, a large tower with a keep which offers visitors breathtaking panoramic views across the town. The castle has stood in Castellina since the 15th century, built to improve Florence's southern State borders. Inside, visitors can find the Archaeological Museum of Sienese Chianti. Established in 2006, the museum displays a collection of archaeological finds illustrating the history of the Chianti area.


Address: Piazza del Comune, 19, 53011 Castellina in Chianti SI, Italy


Tel: 0577-742090
Web: http://www.museoarcheologicochianti.it/en/

The Church of San Salvatore is of 15th-century origin. After being destroyed in the Second World War, the Church was later rebuilt in neo-Romanesque style by the Sienese architect Menotti Lucattell. Inside the Church, visitors can find a fresco of the Madonna and Child by Maestro di Signa; also noteworthy is a wooden statue of Saint Barnabas by a Florentine sculptor.


Address: Via Ferruccio, Castellina in Chianti 53011 SI, Italia

This Gelateria is a favourite for all visitors and locals to Castellina. In 1997, founders Simone and Chiara opened the store, since moving to its current location guests can enjoy their ice cream in the garden. Plus, there is ample parking nearby. The founder’ oldest son also works at the gelateria, and they continue to experiment with new flavour combinations. The shop doesn't just do ice cream but also offers cakes where you will find a large assortment of semifreddo cakes and ice cream cakes. This is a stop not to be missed on your visit to the town.


Address: Via 4 Novembre, 47, Castellina in Chianti 53011
Tel: +39 0577 741337
Web: https://www.gelateriadicastellina.com/

The Rocca delle Macìe company, owned by the Zingarelli family since 1973, is in the heart of Chianti Classico, about a six-minute drive from Castellina. The winery has a long history and offers a selection of wine-tasting experiences. Visitors will get the opportunity to visit the cellar and taste a range of wines produced on-site, encapsulating the colours and flavours of Tuscany.


Address: Loc. Le Macìe 45, 53011 Castellina in Chianti (SI)
Tel: +39 0577 7321
Web: https://roccadellemacie.com/visite-e-degustazioni/

The perfect way to explore the beauty of Castellina and the surrounding Chianti countryside is through scenic walks and cycling routes. Explore many walking trails, hiking paths, and cycling itineraries varying in difficulty and distance. Castellina beckons outdoor enthusiasts in search of serenity and adventure. Whether you're eager to delve into the town or immerse yourself in the surrounding countryside, lace up your walking shoes or rent a bike to savour the breathtaking views at your leisure. 

Explore walking, hiking and cycling routes in and around Castellina here: https://www.komoot.com/discover


Address: Castello di Ama
Localita ama
53013 - Gailoe in Chianti


Tel: +39 0577 746069
Web: https://www.castellodiama.com/en/

For culinary enthusiasts, Castellina is a haven of gastronomic delights, featuring a plethora of restaurants, charming trattorias, and cafes. Indulge in the finest dining experiences, savour traditional Tuscan cuisine, and explore the vibrant food and wine scene at local trattorias and wine bars. Don't miss out on the delectable gelato at Gelateria di Castellina, hailed as the best in the area. Castellina also boasts an abundance of Chianti Classico, with its bottles proudly bearing the trademark Black Rooster (or Black Cockerel). 

Immerse yourself in the rich culinary heritage of the region, where a highly traditional approach to food prevails, offering unique delicacies and seasonal delights like truffles and wild mushrooms. Experience the essence of Castellina through wine tastings, local food specialties, and memorable dining experiences that showcase the true essence of Tuscan cuisine.

La Taverna Squarialupi
Address: Via Ferruccio 26
53011 Castellina in Chianti (SI)
Tel: +39 0577 741405
Web: https://www.tavernasquarcialupi.it/

L'Antica Trattoria alla Torre
Address: Piazza del Comune 15
53011
Castellina in Chianti
Tel: 0577 740236
Web: www.anticatrattorialatorre.com

Bar Italia
Address: Via Trento e Trieste, 34, 53011 Castellina in Chianti SI, Italy
Tel: +39 0577 740258
Web: https://www.baritaliacastellina.it/ 

Gastronomia Porciatti
Address: Via Trento e Trieste, 54, 53011 Castellina in Chianti SI, Italy
Tel: +39 0577 740751

L'Osteria di Fonterutoli
Address: Via Puccini 4, Localita Fonterutoli
53011, Castellina in Chianti
Tel: 0577 741125
Web: www.mazzei.it

Ristorante Riserva di Fizzano
Address: Riserva di Fizzano, Localita Fizzano
53011
Castellina in Chianti
Tel: 0577 737 223
Web: https://www.riservadifizzano.com/

Ristorante La Bottega del Borgo
Address: Via Ferruccio, 76, 53011 Castellina in Chianti SI, Italy
Tel: +39 379 143 8869
Web: https://www.ristorantelabottegadelborgo.it/

There is a car park off via IV Novembre, at the southern edge of Castellina. There is another car park on the northern edge of the village, from where you can quickly reach the historic centre, with views of Castellina along the ridge of the hill as you approach. Parking is harder to find on Saturday morning, during the weekly market.

Most Tuscan towns operate a strict ZTL system, a Limited Traffic Zone. This means that the historic centre is essentially closed to traffic, particularly for non-residents. Cars will need to be left outside the walls.

Road distances from Castellina

Greve in Chianti - 19km
Florence - 50km
Siena - 26km
Panzano - 13km
Radda in Chianti - 11km
Lecchi in Chianti – 18km

Public transport 

Castellina is not the easiest to reach via public transport with no direct train. Buses connect Siena to Castellina or Radda to Castellina but there are no buses connecting Florence to Castellina, going only as far as Panzano.

The Chianti

You could spend a wonderful week or two simply exploring the Chianti, all within a short drive of Castellina. With beautiful landscapes made up of vineyards, woods and towns all to be explored. Some of the most popular towns to visit include Greve in Chianti, the largest in the Chianti region, Montefioralle, Panzano, Gaiole in Chianti, home to one of our villa specialists' favourite pizza restaurants, and Radda in Chianti, the village of vineyards. However, this list is not exhaustive, with many more towns and villages to explore.  

For more information, explore our guide to the Chianti.

Siena is a mere thirty-minute drive from Castellina and makes for the perfect day trip. Sitting proudly in Siena is the Piazza del Campo, one of the most beautiful squares in the region due to its architecture, bell tower and shell-shaped form. Sit at a terraced café on the sloping side of the square and soak up the bustling atmosphere. 

See our Siena guide for more information.

Florence is only an hour's drive from Castellina, making it a perfect outing. Defined by its artistic heritage, the city's churches, palaces and galleries are studded with the world's greatest Renaissance art and sculptures. Balance visits to galleries with wanderings in search of the perfect trattoria or the perfect view. 

See our Florence guide for more information.

Castello di Ama, situated east of Castellina in Chianti, boasts 80 hectares of vineyards and 40 hectares of olive groves in its working wine estate. They are renowned for their Chianti Classico gran selezione DOCG, masterminded by acclaimed winemaker Marco Pallanti. This hilltop estate also doubles as a contemporary art centre, showcasing world-class installations by renowned artists, offering visitors wine tours, tastings, and the chance to explore the sculpture park and Enoteca.


Address: Castello di Ama, Localita Ama, Gaiole in Chianti (Siena) 53013
Tel: +39 0577 746069
Web: https://castellodiama.com/en/

“We enjoyed a delightful stay in Castellina, and it certainly exceeded our expectations. The local deli shop was a highlight, offering delicious Tuscan cuisine for takeaway. The views across Castellina certainly did not disappoint, the panoramic views of endless fields and rolling valleys were simply breathtaking. It was truly beautiful; we can't wait to go back!” 

- Michaela, Social Media and Email Marketing Executive

Feeling ready to start planning your holiday to Tuscany? Discover unparalleled beauty from our villa collection near Castellina in Chianti, where Tuscany's allure comes to life. Embraced by the enchanting landscapes, these handpicked villas offer a haven of tranquillity and sophistication. Located in a region steeped in history and culinary excellence, you will not be short of new activities. From savouring the world-renowned Chianti wines to wandering through the cobblestone streets of historic towns, every moment is a celebration of Tuscan culture. Our carefully selected collection of villas, varying in size and amenities, ensures an authentic yet comfortable experience.

Explore our Siena and Chianti villas to start planning your Tuscan holiday today. Alternatively, entrust your holiday planning to our team of Villa Specialists. With their firsthand experience and intimate knowledge of the region, they'll ensure you find the ultimate Tuscan holiday tailored to you.