Famous all over the world for the production of wine, the Chianti borders have never been clearly defined, but we could say that it extends from the southern provinces of Florence to Siena, covering the whole area between the two cities and stretching towards the east and west. The most visited Chianti towns are Castellina, Radda and Gaiole; however, this alternative one day itinerary will take you a little bit off the beaten track, giving you the opportunity to explore Badia a Passignano, Radda in Chianti, Volpaia and Montefioralle.
Surrounded by vineyards and olive trees, the Badia a Passignano (Abbey of Passignano) dates back to the 11th century and dominates the village of the same name, which is no more than a cluster of houses and an osteria. However, with its walls and towers emerging from the middle of a cypress grove, it is definitely worth visiting – a photographer's delight. The Abbey's dining hall also houses a massive, 21-foot-wide Last Supper by Domenico and Davide Ghirlandaio, two great figures in the history of Florentine painting.
The second stop on this tour is Radda in Chianti, located just 1 hour from Florence: the town has maintained its Medieval charm and is still surrounded by ancient city walls. Take a stroll along its narrow streets, look for Piazza Ferrucci and visit the Palazzo del Podestà (15th century) and the Romanesque Church of San Niccolò; after lunch, just outside the town centre, you can also visit the Franciscan Convent of Santa Maria in Prato, which dates back to the Middle Ages.
The picturesque, fortified village of Volpaia is situated on a hilltop just 7.5 km north of Radda; peaceful and quiet, it was built in the 11th century and although only two of its original six towers are still standing, it is one of the best preserved villages of its period. Just as it has been for the last 900 years, the entire village is intimately involved in the production of organic wine and olive oil and most of the employees of the Winery live within the village's walls.
On the way back to Florence (via SR222), take your time to visit Montefioralle that is claimed to be the birthplace of Amerigo Vespucci (a house on the circular main street inside the village has his family's coat of arms – a V and a wasp – above the doorway). Tiny and cute, the Village has charming stone buildings, some small shops, a couple of good restaurants and a nice family-run winery with surprisingly good (and fairly priced) wines.
You can obviously organize this excursion yourself or, if you don't feel like driving, you can contact someone specializing in Tuscany tours. Whatever option you may choose, I hope you have a very good time in Chianti!
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