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Best itineraries in Tuscany - the Sienese Chianti villages

Nature, history and culture, a territory with so much to offer that of Chianti. Famous for its wine and its landscapes of endless rows of vines, and its characteristic villages. The Chianti area includes the municipalities of Greve, San Casciano, Barberino Tavarnelle, Gaiole, Castellina, Radda and Castelnuovo Berardenga.Let us continue the column of the best itineraries in Tuscany according to Borgo Scopeto with the villages of the Sienese Chianti.

Castelnuovo Berardenga

20 km from Borgo Scopeto


The village of Castelnuovo Berardenga was founded in 1366 by the city of Siena, which is about 20 km away. It was built as a lookout castle for the city thanks to its position on the border with the territory of Florence. Its name derives from the Count Berardo of the Frankish population who lived on that site. It remained under the control of Siena until 1555, when it passed under the control of Florence. It is called the "slow city" for its slow and peaceful lifestyle. Characteristic is the Vicolo dell’Arco with its red brick arches and the remains of the lookout tower in Piazza Petrilli transformed in 1755 into a clock tower. Not to be missed outside the city is Villa Chigi Saracini, surrounded by an enchanting Italian Renaissance garden and an English park, commissioned by Count Guido Saracini, founder of the renowned Chigiana Music Academy in Siena.

Radda in Chianti

20 km from Borgo Scopeto


Radda has very ancient origins, the first traces of settlement date back to 2000 BC. It developed in the Middle Ages under the Guidi family of Florence and became the capital of the Lega del Chianti, a political-military coalition founded by the Republic of Florence to defend the Chianti area from the attacks of Siena, together with Castellina and Gaiole. In the seventeenth century, when the conflicts ended, all the surrounding fortifications became private castles of noble families who dedicated themselves to the production of wine, such as the castle of Volpaia. From these in 1716 the Consortium for the Protection of Chianti Wine was born. Today it still retains its original medieval appearance with the ancient walls surrounding the city center. To see the Palazzo del Podestà, it was used for four centuries by the Captain of the Chianti League, as recalled by the many coats of arms on the facade, the Church of S. Niccolò, of Romanesque origin and on the outskirts of the town the Convent of the Franciscans of Santa Maria in Lawn.

Gaiole in Chianti

14 km from Borgo Scopeto


The Borgo di Gaiole also has medieval origins. It was an important center of trade between the various surrounding settlements, thanks to its position halfway between the Chianti and the Valdarno. All around Gaiole there are beautiful castles and fortified fortresses, today owned by wine producing families, such as the Castello di Brolio, Meleto, Vertine, the Badia a Coltibuono and the Pieve di Spaltenna.

Castellina in Chianti

15 km from Borgo Scopeto


Castellina is a village of ancient origins, founded by the Etruscans, as evidenced by the Etruscan tombs in the Montecalvario area. It was an important military strategic point between Siena and Florence, being at the crossroads of the four areas of Chianti. Do not miss the imposing fortress that dominates the central square and the suggestive walkway of Via delle Volte that crosses the whole town that offers breathtaking 360 ° views of the surrounding countryside and of Sienese and Florentine stately palaces. Do not miss the Church of San Salvatore and the Archaeological Museum of Chianti Senese.

These villages of the Sienese Chianti are for us among the best itineraries in Tuscany. Do you agree? Which ones have you visited and which ones would you like to visit?

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