Photo ©Davide Taviani
Three days in Chianti, among wineries and villages
Travelling between Barberino Tavarnelle and San Casciano Val di Pesa in the surprising Chianti area
38 km
3 days

Chianti is one of the most loved and well-known areas of Tuscany for the undeniable beauty of its landscape that's shaped by vineyards and olive groves, and for its fascinating villages that are rich in history.

To visit a lesser-known corner of Chianti, we propose a three-day itinerary that winds through the towns of the Val d'Elsa from Barberino Tavarnelle to San Casciano, passing through historic wine cellars, fortified villages, and centuries-old parish churches.

Day One
Among Romanesque churches, medieval villages and wine cellars
Antinori wine cellars
Antinori wine cellars 

Let's start from Tavarnelle Val di Pesa: don'tmiss a visit to the Parish Church of San Pietro in Bossolo which dates back to the 11th century and is one of the most beautiful examples of the Romanesque that can be found in the Florentine countryside.

Here, you can visit the Sacred Art Museum, where works from the local churches are gathered together. Inside, there's a space dedicated to embroidery and in particular to Tavernelle lace, with splendid hand-made objects including examples made by local embroiderers on behalf of Salvatore Ferragamo.

We then head towards San Casciano in Val di Pesa in Bargino, where the Antinori Winery is located: the innovative building designed by the Archea Associati studio is a work of art hidden among the olive trees and vineyards. The one-hour visit to the cellars is a journey through the history of the Antinori family, which has been producing wine in Tuscany since 1385. The tour covers all stages of production, from the vineyard to the glass, ending with a tasting of three wines.

The afternoon is dedicated to discovering the picturesque medieval village of San Donato in Poggio, located on a hill overlooking the road that connected Florence and Siena. Stroll through the streets of the fortified village that's surrounded by high defensive walls and which has preserved two centuries-old entrance gates and watchtowers. Just outside the town is the Parish Church of San Donato, with a magnificent terracotta baptismal font by Giovanni della Robbia.

Day Two
From the history and flavours of Badia a Passignano to the Astronomical Observatory
Badia a Passignano
Badia a Passignano 

The village of Passignano is the starting point of our second day, leading us to discover the Abbey of San Michele Arcangelo in Passignano, a historic monastery of Vallombrosan monks that has existed since the year 1000 and looks like a castle given that it was fortified over the centuries. Still today, it's surrounded by walls built in the fifteenth century and preserves many works of art including Ghirlandaio's Last Supper fresco.

Badia a Passignano and its surroundings are perfect for a lunch based on typical Chianti products. There's bistecca alla fiorentina (Florentine steak), of course, but also ribollita (well-known Tuscan soup made with black cabbage), crostini with livers and local salami such as finocchiona.

After lunch, we move to the village of Sambuca Val di Pesa, with evidence dating to 1053 thanks to the famous castle. Here we can find the bridge of Romagliano, over which the ancient Via Regia Romana passed. The stone bridge with three arches was rebuilt in 1415, but originally dates back to 1100. For a walk in nature, we can follow the course of the river Pesa in the footsteps of San Giovanni Gualberto: the large boulders that we meet along the way reveal to us the legend according to which the devil threw these boulders at the saint, who instead made them lay gently on the ground. At the chapel dedicated to San Giovanni Gualberto, we can find the boulder on which he lay down to rest, said to have the imprinted shape of his body.

Sambuca is also an important centre for artistic craftsmanship, and is home to stores with magnificent masterpieces of  hand-made jewellery.

The last stop is the Chianti Astronomical Observatory, where you can observe the sky, spot the moon and other planets. For information on guided tours:

Day Three
Barberino Val d’Elsa and Semifonte, craftsmanship and architecture
Chapel of San Michele Arcangelo in Semifonte
Chapel of San Michele Arcangelo in Semifonte 

The third day is dedicated to Barberino Val d’Elsa, a characteristic village overlooking the Chianti area that like Sambuca, is dedicated to crafts. Along the main street and in the surroundings, there are stores and workshops where historic crafts give life to unique pieces with a sometimes traditional, sometimes modern taste. Walking in the historic centre of the town, you can look into the ateliers and witness the work of the masterful craftspeople at work.

Without leaving Barberino, we head to the second stage and see a true gem of Chianti that's hidden in the countryside around Petrognano: the Chapel of San Michele Arcangelo in Semifonte, built on the model of Brunelleschi's Dome, of which it's the perfect copy in reduced scale, equal to one fifth of the original. The chapel looks like it's inside a charming circle of cypresses and, according to a local legend, brings luck to lovers: couples come here to make three laps around the building to attract good luck, a perfect rite to conclude our three day trip to Chianti.