The Chianti region - 20 km from San Gimignano


The Chianti region offers a unique and evocative panorama. It is characterized by green hills with kilometers and kilometers of vineyards and olive groves and narrow villages between large medieval walls and winding streets.
Below we have designed for you some daily itineraries with starting point in San Gimignano.

  • Barberino Val d’Elsa: is a beautiful medieval village between Florence and Siena surrounded by the green Tuscan countryside. The secondary road that leads you from San Gimignano to Barberino Val d’Elsa and the corners of the town offer breathtaking views over the Chianti region. To the right side of Porta Senese (the medieval gate of the village) you will find the Pasolini Dall'Onda Borghese Winery, which is definitely worth a visit! Their cellars are located in the medieval basement of the town, where their excellent wines are fully refined, aged and bottled. Moreover, in the mill of the farm, is produced one of the the extra virgin olive oil considered by experts among the finest in the area.
  • It’s worth a visit also the fortified village of Badia a Passignano and its Protected Natural Area, perfect for trekking lovers in an uncontaminated landscape with breathtaking views.
  • The village of San Donato in Poggio is also a mandatory stop.
  • Continue to Greve in Chianti, considered the gateway to the Chianti region, famous for its particular square, which since the Middle Ages was the market of the villages, castles and farms of the surrounding hills.
  • Finally Panzano with the Antica Macelleria Cecchini, famous for its excellent Florentine steak, where sometimes you can heard the butcher reciting lines from Dante’s Inferno.

Between Florence and Siena, in the Chianti area, there are many Villa/Castle that are worth a visit.

  • The Castle of Verrazzano is famous as here was born the navigator Giovanni Da Verrazzano, who discovered the bay of New York and most of the east coast of the current United States. A visit to the Castle, gardens and the historic cellars is necessarily followed by a tasting of their wines.
  • The Castle di Brolio dominates the southern part of the Chianti Classico and since medieval age belongs to the important Tuscan family of Ricasoli. The Italian gardens and the romantic park that surrounds the castle are very suggestive. From the garden you can enjoy a breathtaking view of the Ricasoli estates and the city of Siena. Inside the Castle you can visit the Chapel, the family crypt and the museum of the Ricasoli Collection. Do not miss a visit with a tasting at their cellars and an excellent lunch at the Osteria of the Castle.

Southern Chianti also deserves its itinerary.

  • Starting from Castellina in Chianti, a picturesque village that still maintains the typical shape of the ancient medieval fortifications, the Rocca with its imposing tower offers a spectacular view of the city and the surrounding countryside.
  • Continue along the famous Strada Chiantigiana, until Radda In Chianti, where the evocative atmosphere reigns inside the ancient walls, the squares and the marvelous panoramas over the landscape.
  • Visit also Gaiole in Chianti, the wonderful hamlet of Vertine and Badia a Coltibuono with the church, the cloister, the Italian gardens and the cellars.

Whatever your destination in Chianti is, it is impossible not to stop and taste its wine. The Chianti wine-growing area is larger than the towns that make it up. Many farms and wineries require reservations, for others it is sufficient to show up but it is always preferable to get in touch first to organize an excellent tasting.