Things to do in Gaiole in Chianti and around
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Gaiole in Chianti: wine, castles and… heroic cyclists

Gaiole in Chianti is a small town in province of Siena, located on the road that leads from Chianti to Montevarchi and the Valdarno. We are in the Chianti region and the land around Gaiole has the typical landscapes of the area made of rolling hills richly cultivated with vineyards and olive groves alternated to oak woods.

Gaiole developed since the 13th century when, with Radda in Chianti and Castellina in Chianti, was one of the main town of the Lega del Chianti. In that period Gaiole became important also for its role of market very renowned among the various centres and the numerous castles in the area.

Until the final victory of Florence against Siena in 1555, the area around Gaiole in Chianti was contended by these two major Tuscan town and Gaiole suffered many attacks. After these wars, Gaiole devoted itself more and more to agriculture and to its role as a market town.

Vineyards in Chianti
Vineyards in Chianti (Photo by Allan Harris / CC BY)

Things to do in Gaiole in Chianti and around

Gaiole is a nice hamlet gathered around his large central plaza that today hosts many cultural initiatives and events related to wine. Unfortunately Gaiole does not retain much of its ancient monuments, suffice it to say that the most important Church of the village, Church of San Sigismondo, dates back to the 20th century even if inside there is a seventeenth-century piece of art representing the Virgin of the Rosary. Nevertheless, Gaiole is a valid holiday destination thanks to its traditions and the many monuments scattered around its territory.

Around Gaiole in Chianti you can visit some very interesting castles, churches and villages:

  • Pieve di Spaltenna
  • The village of Vertine
  • Badia a Coltibuono
  • Castle of Brolio
  • Castle of Meleto
  • Pieve di San Polo in Rosso

Pieve di Spaltenna

You can easily get to the Pieve di Spaltenna and the related structures by foot from Gaiole, because it is located just outside the town. Splatenna as a place is documented since the year 1030 while the current Romanesque parish church dates back to the first half of the 12th century. The facilities connected to the church, once fortified, have been converted into a hotel.

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

The small village of Vertine

Vertine is a  tiny fortified village located on a hilly area about 2 kilometres far from Gaiole. Documented since the 1013, Vertine has very well preserved its medieval structures as the massive tower near the arched 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)

Badia a Coltibuono

Founded around the year 1000, the Badia di Coltibuono is a benedictine monastery converted into a villa-farm after the 1810, when the monks left the abbey. Surrounded by green forests, this former monastery complex offers many points of interest. Today you can visit the historic monuments as the Romanesque church of San Lorenzo and the cloister of the Abbey or do a tasting of wines produced by the winery.

Guided tours:
24-31 March, April, October – 4 November: 14.30-17.30
May – September: 14.30-18.30

Tickets: 7 euro for the guided tour; 10 euro for guided tour + tasting

Web site

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

Castle of Brolio

The grandiose castle of Brolio is located south of Gaiole in Chianti, on the road to Castelnuovo Berardenga. Property of the Ricasoli family since the 12th century, this outstanding Castle which was built in the 11th century, is the most important and famous monument of the area. You can visit the castle and the the seals of the Ricasoli family by booking a guided tour. For more informations, please consult the official website.

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

Castle of Meleto

Another important fortress is the castle of  Meleto. The castle of Meleto is documented since the 11th century when was a possession of the Badia di Coltibuono. Subsequently acted as a military outpost of Florence to become then a villa when the area was pacified. Today this impressive military complex is home to a company that produces wine and can be visited by reservation.

Web site

Things to do in Gaiole in Chinati: visit the Castle of Meleto
Castle of Meleto (Photo by Vignaccia76 / CC BY)

Pieve di San Polo in Rosso

The pieve di San Polo in Rosso is an excellent example of a fortified parish church. Built during the 11th century, the Church has a Romanesque etyle with Gothic additions; inside there are some 15th-century frescoes.

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

L’Eroica at Gaiole in Chianti

Gaiole is also famous for being the original premises of departure and arrival of the Eroica, a famous race that commemorates the cycling of yesteryear. If you want to join those fabulous riders aboard vintage bicycles whizzing by on the dirt roads of Chianti, I suggest you to read our article about the Eroica, where you’ll find all the information you need.

Eroica bike
Eroica (Photo by ian / CC BY)
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