Chianti is a region not very extensive but very rich from the naturalistic, historical and artistic point of view and generous for its food and wine. That’s why there are infinite perspectives and possibilities of routes between its hills, its natural landscapes and the medieval villages, remained unchanged over time.


The Chiantigiana road between the most beautiful in Italy, runs through the Chianti from Florence to Siena. Follow it is a great way to discover the territory.

From Florence, take the SS222 road towards Greve in Chianti. The country is the heart of the Chianti Classico production zone and worth a visit. two roads branch off from here: one leads to the valley of the Arno near Figline and St. John’ss along the high hills, the other narrow and partly unpaved rejoins the Via Cassia near Sambuca Val di Pesa going from village Montefioralle and Passignano.

Continuing on the Chiantigiana Panzano meets, the last outpost of the Florentine Chianti and continuing to the junction you can be reached by a side of Radda in Chianti and other Castellina. From the latter you can go down to the Elsa and go back to San Gimignano, Monteriggioni and visit to Siena.

If you go towards Radda, however, the landscapes are made less extensive but it’s great historical importance and present of this country in the Chianti wine tradition. Taking the Chiantigiana you get to Gaiole in Chianti.

All around the area is rich in castles and villages. Examples are Spaltenna, Vertine and Barbischio. Continuing Siena meet a number of direct routes to the most beautiful places in the area, where Castelli as Bolio, Apple Orchard, Castagnoli, blend into the landscape endless vineyards, woods and medieval villages such as the beautiful Lucignano.

The tour ends at the gates of Siena.


The southern part of Chianti is made up of the four municipalities in the province of Siena: Castellina in Chianti, Radda in Chianti, Gaiole in Chianti and Castelnuovo Berardenga.

ITINERARY: from Castellina in Chianti in Castelnuovo Berardenga through Radda in Chianti and Gaiole in Chianti. LENGTH: 46 km

Along the stretch of road between Poggibonsi Castellina in Chianti are the ruins of Monterano, castle appointed since 1089 and certainly one of the most powerful and vast buildings of the Valdelsa. Once in Castellina, the fifteenth-century Rocca Comunale overlooking the old town. Inside the Etruscan Museum collects the numerous Etruscan objects discovered in these areas. Nearby it is instead the Hypogeum of Mount Calvary, an imposing Etruscan tomb considered the most important found in Chianti.

After traveling for 12 km SR429 you reach Radda in Chianti medieval village with Gaiole in Chianti, the capital of terziere at the time of the Chianti League.

Two major tours: one to the church of Santa Maria a Spaltenna, the other in the village of Vertine, once owned by the Ricasoli family. Proceeding lie in succession the Brolio Castle and the small village of San Gusme, Sienese stronghold against Florence.

The itinerary ends in Castelvuovo Berardenga, Siena, where he built the last castle. Although a good part of it still is part of the municipality, Castelvuovo is located outside the boundaries of Chianti Classico.


The northern part of the Chianti region comprising the municipalities of San Casciano Val di Pesa, Tavarnelle and Barberino Val d’Elsa

Leaving Florence after traveling 23 km meets San Casciano Val di Pesa. On this road May 21, 1891 was inaugurated Train of steam Chianti. Located in the extreme northern part and inserted only partly in the territory of Chianti Classico, San Casciano is a primitive village developed at the Pieve di Santa Cecilia a Decimo.

Leaving San Casciano after 16 km you arrive at Tavernelle Val di Pesa, ancient village mentioned already in a 780 parchment.

Nearby, to visit the beautiful fortified village of the Abbey and the church of S. Donato in Poggio.

A few more kilometers and you get to Barberino Val d’Elsa, the last leg of this journey. Here you can pay a visit to the Chianti Botanic Park divided into four categories: flowering plants, woodsy, aromatic plants, varieties of fig tree.

To visit the area in the Paneretta Castle, Monsanto and the Pieve di S. Appiano.