The best places to visit in Chianti
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The wonderful Chianti hills

Chianti is certainly one of the most beautiful and famous areas of Tuscany. Everyone knows the Chianti region, its gentle hills cultivated with vines and olive trees represent in the collective imagination the Tuscan countryside more than any other area; perhaps only the Val d’Orcia enjoys a similar fame.

Although it does not have clear boundaries, we can say that the territory of the Chianti Classico extends between the province of Florence and that of Siena. Historically, only the territory of Gaiole, Radda and Castellina that formed the so-called Lega del Chianti was considered as chianti; today, the territories of Greve in Chianti, Castelnuovo Berardenga,San Casciano and Tavarnelle in Val di Pesa, Poggibonsi and Barberino in Val d’Elsa are also considered Chianti.

From a viticultural point of view the protected area of ​​Chianti extends further in all directions: to the west to the Pisan hills; to the north to the Pistoia hills and to the Rufina area; to the east on the Aretine hills and to the south on the Sienese hills.

Chianti countryside
Chianti countryside (Photo by  Francesco Sgroi / CC BY)

Places to visit in Chianti

The fabulous wines and the spectacular panorama are certainly two very important attractions, but Chianti also enjoys numbers of villages, castles and many other monuments scattered over its territory between an olive tree and a row of vines. Let’s see together which are the most importante places to visit in the Chianti Classico:

Greve in Chianti

Being in the northernmost area of the Chianti Classico, Greve in Chianti is usually considered the gateway to Chianti. It is a market town, born under the neighboring Castello di Montefioralle, which has in its main square the focal point of the entire historical center. Near this square there are the statue of Giovanni da Verrazzano, the palazzo del Comune and the chiesa di Santa Croce. Not far away we find the Museo d’Arte Sacra di San Francesco.

Greve in Chianti things to do: visit the Chiesa di Santa Croce
Chiesa di Santa Croce (Photo by charley1965 / CC BY)


Montefioralle is a pleasant medieval village located in the municipal territory of Greve in Chianti, which is just over a kilometer away. It is a real gem perfect for a nice relaxing walk. Among the buildings of Montefioralle, look at the chiesa di Santo Stefano and the house of Amerigo Vespucci; near Montefioralle, the beautiful pieve di San Cresci is also worth a visit.

Montefioralle (Photo by Elisa Rolle / CC BY)

Radda in Chianti

Ancient capital of the Lega del Chianti, Radda is a hamlet to be explored. Inside the walls there are the Palazzo del Podestà and the Propositura di San Nicolò, both overlooking the central square, just outside the walls we find the Ghiacciaia Granducale, a particular structure that was once used to store the winter snow to be transformed into ice.

Things to do in Radda in Chianti: visit the Palazzo del Podestà
Palazzo del Podestà in Radda (Photo by / CC BY)

Castellina in Chianti

Located in a beautiful position halfway between Florence and Siena, Castellina in Chianti is a beautiful town that has the main monument in the Rocca. Inside you can visit an interesting archaeological museum, while from the top of its tower you can enjoy a beautiful view of the Chianti. During your visit to Castellina, do not miss out on the Via delle Volte where there are several restaurants, shops and shops.

Things to do in Castellina in Chianti: visit the Fortress
The Fortress of Castellina in Chianti (Photo by Vignaccia76 / CC BY)


Vertine is a small fortified village located in the municipality of Gaiole in Chianti, a couple of kilometers from the capital. Known as a castle since 1013, Vertine has very well preserved its medieval structures and the particular the imposing tower that is located near the entrance to the village.

Things to do in Gaiole in Chinati: visit the hamlet of Vertine
The village of Vertine (Photo by Vignaccia76 / CC BY)

Pieve di Spaltenna

Easily reachable on foot from Gaiole in Chianti, the Pieve di Santa Maria in Spaltenna is a beautiful example of Romanesque ecclesiastical architecture. The church is characterized by a salient façade with a mighty bell tower on the left.

Things to do in Gaiole in Chinati: visit the Pieve di Spaltenna
Pieve di Spaltenna (Photo by Renzo Ferrante / CC BY)

Badia a Coltibuono

Born around the year 1000 as a Benedictine monastery, the Badia di Coltibuono was transformed into a villa-farm in the early nineteenth century. The abbey enjoys a beautiful location surrounded by lush forests and is today the heart of a winery where you can taste the products during the visit.

Things to do in Gaiole in Chinati: visit the Badia a Coltibuono
Badia a Coltibuono (Photo by Bit Boy / CC BY)

Castello di Brolio

Here we are at what is perhaps the most famous monument of all the Chianti Classico: the Castello di Brolio. We are still in the municipal territory of Gaiole in Chianti, among hills cultivated with vines or olive trees and thick forests of oak and chestnut trees; in this true paradise stands the Castle of Brolio with its brick building that stands out with its large size in the surrounding landscape. The castle, owned by the Ricasoli family since many centuries, is the seat of one of the main wineries in the Chianti area; during the visit, do not miss a wine tasting!

Things to do in Gaiole in Chinati: visit the Castle of Brolio
Castle Brolio (Photo by  judywitts / CC BY)

Pieve di San Polo in Rosso

We remain in the territory of Gaiole to talk about the Pieve di San Polo in Rosso. This is an interesting Romanesque-Gothic religious building, that in the fourteenth century was transformed into a fortification of which even today you can appreciate the walls and some defensive towers.

Pieve di San Polo in Rosso
Pieve di San Polo in Rosso (Photo by LigaDue / CC BY)

Castelnuovo Berardenga

Located on the border with the Crete Senesi, Castelnuovo Berardenga is the southernmost municipality of the Chianti Classico. Born in 1366 as a castle of the Republic of Siena, Castelnuovo Berardenga does not retain much of its original defensive structures, only a tower and some traces of the walls. Among the main monuments to see are the Propositura dei Santi Giusto and Clemente and the Villa Chigi Saracini.

Things to do in Castelnuovo Berardenga: enjoy the panoramic view
Castelnuovo Berardenga (Photo by Michal OsmendaCC BY)

Barberino Val d’Elsa

Barberino Val d’Elsa is an ancient village halfway between Florence and Siena whose history is linked to that of Semifonte, the city that no longer exists. In the historic center of the town there are several monuments such as the Chiesa di San Bartolomeo and Palazzo Pretorio while in the surroundings you can admire the Pieve di Sant’Appiano, the Castle of Tignano, the Badia a Passignano and the Cappella di San Michele Arcangelo which located where the city of Semifonte once stood.

Pieve di Sant'Appiano
Pieve di Sant’Appiano (Photo by Johnny Johansson – Kaneos Media)

San Casciano Val di Pesa

San Casciano Val di Pesa is a very interesting village which is located just 15 kilometers from Florence. Here there are several things to see such as the Collegiata di San Cassiano, the main church of the city, and the Torre del Chianti from which you can enjoy a very wide panoramic view. In San Casciano I also recommend you to visit the Museo Giuliano Ghelli where you will find many works of sacred art and an archaeological section with finds from the Etruscan era.

Things to do in San Casciano Val di Pesa
San Casciano Val di Pesa (Photo by Johnny Johansson – Kaneos Media)
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