Discover Tuscany from your Villa: Four days in Chianti

The classic Chianti, or Chianti Classico, comprises the provinces of Florence and Siena in Tuscany. It expands over a large territory in the center of the region starting right above the city of Siena and expanding north towards Florence, ending not far from the capital of Tuscany. It is an area of rare beauty in Italy, where you will find many Tuscan villas for rent. The most important towns of Chianti are Castelnuovo Berardenga, Radda, Greve, Castellina, Gaiole in Chianti, San Casciano, Tavernelle, Barberino, Colle Val d’Elsa, and Poggibonsi among others. This will be an itinerary through some of these towns that should take you about four days to complete.

Day 1

From Castelnuovo Berardenga to San Gusme

Supposing you are staying in a Tuscan Villa near Siena, the first day of your tour will be Castelnuovo Berardenga. It is a delicious town that originated around the year 1000 as a defensive castle of the Siena territories. Among the most interesting things to see are the church of San Giusto a Clemente, the church of Madonna del Patrocino, Villa Chigi Saracini, a 19th century monumental building in classical style, and the Museum of Landscape. Around Castelnuovo you should visit the wine farm of Felsina for a wine tasting, and then proceed to visit Villa Arceno and the small town of Villa a Sesta. In addition you should not miss out on the village of San Gusme.

Day 2

From Gaiole to Cavriglia

On the second day of the tour, head towards Gaiole in Chianti. It was first incepted during the 11th century as a market town. Here is where in the past the president of the Chianti league resided. Among the most interesting things to see here is the original fountain of the marketplace, and the nearby San Pietro in Avenano. This is a church complex from the 10th century, which played a fundamental role in the life of the area. It was rebuilt in 1530 in Gothic style with the high altar attributed to Andrea Della Robbia. Move along towards Pieve a Spaltenna to visit the church of Santa Maria, then to the village of Vertine to admire the castle from the 11th century. Badia a Coltibuono rests on the way to Cavriglia on the side of the Chianti mountains. Probably built during the eighth century, it is a severe monastic complex with huge crenelated belltower.

Day 3

From Castellina to Sienese Chianti

On the third day of your tour visit Castellina in Chianti and Radda in Chianti. Radda in Chianti originated during the 11th century BC. The castle functioned as a defensive stronghold against Siena in the war with Florence. The most interesting buildings to visit are the palace of Podesta, and the church of St. Nicholas. Around Radda you should visit Santa Maria in Prato and Vercenni, Castle of Aiola, Volpaia and Panzano in Chianti. From here go to Castellina in Chianti, located on a hill surrounded by vineyards. It originated during the seventh century BC, and later became another stronghold of Florence against Siena. Visit the church of San Salvatore and the Palazzo Squarcialupi, a noble palace now the seat of Fattoria la Castellina, owner of many Tuscan villas in the countryside, and a wine maker. You can close your visit with the Archaeological Museum of Sienese Chianti.

Day 4

From Barberino Val d’Esa to Greve

On the last day of your tour you should visit Barberino Val d’Esa and Greve in Chianti. Barberino Val d’Elsa dates from the 11th century as a fortified stronghold of Florence against the area’s feudal powers. The town is very well preserved and maintains its elliptical plan crossed by two main roads. The most important palaces in town are that of Podesta and Palazzo Barberini that belonged to the family whose descendant was Pope Urban VIII who sentenced Galileo. In the area you should visit Poggibonsi, Petrognano and Sosta del Papa. Proceed to Greve in Chianti, which was also founded during the 11th century. Originally the marketplace of the castle of Montefioralle, by the 15th century it had acquired a strong importance in the area. Nearby you should visit the castle of Verrazzano that belonged to the family of the famous seafarer Giovanni da Verrazzano. Greve is strongly bound to wine making, with many farms in the area renting their holiday Tuscan villas, therefore the Museum of Wine is a must see. The town square also hosts the Museum of Sacred Art, which once was a hospice founded by St. Francis of Assisi.

Photo credits (in order of appearance): nubui (featured photo)

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Tags: chianti, italy, itinerary, tuscany

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