Chianti Classico wine and olive oil trail

San Donato in Poggio (a fraction of Tavarnelle Val di Pesa) is a town full of charm. It has existed since 989 AD, the year in which it appeared in a document from Badia a Passignano. The center of this medieval village features Palazzo Malaspina, which is one of the most important architectural buildings of the sixteenth century.

Perched nearly 500 meters above sea level, here you can take a walk through the old village and visit the church of San Leolino, one of the most important Romanesque churches of the Chianti area.It holds beautiful works by artists such as Giovanni della Robbia and Raffaelino del Garbo.Panzano in Chianti is also well-known for Vino al Vino, a wine festival held on the third weekend in September, and home to the famous butcher Dario Cecchini.

A stop-off in Castellina may obviously include tasting at the numerous wine lodges, but you can also get to know the great art of Chianti pork-butchers whose charcuterie is highly prized for its unforgettable flavours.

Radda is the vineyard village. From the high ground on which it was built in the middle ages, between the waters of the rivers Arbia and Pesa, you gaze over a very dense interweave of vineyards. The centre of the village, dominated from above by the remains of the original castle, is Piazza Ferrucci.Don’t miss the view over the alleys of the old centre and the vegetable gardens, surrounded by dry stone walling, which supply the essence of Chianti: agriculture in the form of design of the landscape in a natural order of men and things.

Gaiole, founded between the 13th and 14th centuries, had trading rather than military origins. At first it was a market serving the many castles dotted around the surrounding territory. So the heart of Gaiole (which today is one of the Cinta Senese breeding centres) is a street-marketplace: via Ricasoli where the market was and still is held and which is the hub of local life.Gaiole offers the chance to shop for fine wines and foods, and also has some quality hotels. And of course there is the fascination of the ancient houses, the riverside and the urban furnishings which recall mediaeval trading activities.

Castelnuovo witnessed the battle of Montaperti, central to the history of Siena: in 1260 the Florentine army was defeated by the Republic of the Palio.After Montaperti the Sienese Republic decided to supply its new outpost with new fortifications (hence the name, which means New Castle) but they were never completed. Evidently this stretch of Chianti was destined for peace and cultivation of the spirit rather than for military defence.A visit to Castelnuovo Berardenga cannot exclude the Villa Chigi Saracini with its superb architectural elegance embellished by a formal garden. It is enriched above all by a 19th century park of considerable botanical importance.

Greve in Chianti is the only town in the province of Florence that rests entirely in the Chianti area. In antiquity, Greve was a small center in the territory, then called Agro di Florentia. The Romans were the first to live permanently in these places not far from the via Cassia. Indeed, local place names are a trace of the Romans’ time here, such as Siliano, a town that takes its name from a colony of veterans of Sulla who established themselves here.The origins of Greve in Chianti date to the Early Middle Ages.