For the part of the itinerary can start from Siena and Siena from here with the SR 222 to reach Castellina in Chianti
Castellina in Chianti is located in a beautiful hillside location, nestled between the valleys, Elsa and Pesa. His district is entirely contained in the Chianti Classico. Among the most important center of Chianti and resorts in constant development. Etruscan and Roman origin, a fief of the Nobles of Trebbio (XI century), was also an important Florentine garrison. The ancient capital of the Chianti League with Radda and Gaiole in the thirteenth century, then, in the fourteenth and fifteenth centuries, Castellina was the scene of raids and looting. The Florentines surrounded the city walls in 1400-1402. Dominated by the historic fortress, consisting of a defensive building high and surmounted by a keep, still more grandiose, presents medieval fortifications and traits, such as the picturesque Via the Times. The town retains some of its four-century character. At 100 meters from the center of Castellina, along the road to Greve, is a large Etruscan tomb dating to the sixth century before Christ, the Mound of Montecalvario, it is the most interesting local archaeological discovery, evidence of an ancient presence human in Chianti. Many interesting and all the churches in the area. Of particular value to those of San Martino Cispiano, who has retained all its grace Romanesque, with a beautiful apse and nave, and you soon in the Coinage, which houses a Madonna and Child by Lorenzo di Bicci. Rich in history, is the village of Fonterutoli, mentioned in a document of 998. In the neighborhood of Fonterutoli is the Necropolis of Poggino with the remains of Etruscan tombs.
In the southern slopes of the Chianti, 20 km from Siena, is Castelnuovo Berardenga , which tells its origins in the name of a fortified village, situated on a hill between the river and the Ombrone Malena, a ' area traditionally famous for its agricultural products still based on wine production of wrought iron handicrafts. The castle, founded in the last area, of which there are a tower and some ruins, was built in 1366 by the City of Siena with the intention of giving prominence to Castelnuovo functions on the territory of Berardenga. In the town, a beautiful park surrounds the Villa Chigi. At nearby Pacina, the great church of Santa Maria Maddalena, of medieval origin but rebuilt. Charming little fortified town of San Gusmè, in which the two original doors remain stone-arched. In a lovely hilly area, the center of a beautiful valley, then rises Vagliagli, standing next to the castle of Aiola. In the municipal area stands out for the imposing Certosa di Pontignano, founded in 1343 and rebuilt in the second half of the `500.

Going north we meet Gaiole in Chianti , wine center and holiday resort surrounded by green hills thickly planted. The town developed as a market place in the middle of the thirteenth century, when it became one of the cavalier of the ancient capitals of the Chianti League, which were also part of Castellina in Chianti and Radda in Chianti. Just west of the town `, between woods and vineyards, there are two medieval fortified complexes: the parish church of Santa Maria a Spaltenna (first half century. XII) and the village of Vertine, documented by the tenth century castle, surrounded by a walled perimeter of oval, with entrace door guarded by an elegant tower. Among the main attractions of the entire Chianti, Brolio Castle, home of one of the largest wineries, is among the first examples of a fortified bastion in the Tuscan area. Built by the Florentines, on pre-existing, after 1484, has impressive polygonal enclosure, within which you have the vast building Romantic style built in 1860 by architect Marchetti on behalf of Baron Bettino Ricasoli. Other castles in the area, those of Meletus and Cacchiano.
Radda in Chianti , set on a hill that marks the watershed between the valleys of the Pesa and Arbia. Today the center predominantly agricultural (wine production), Radda has an ancient history passed by Guidi in Florence in 1203, had fortifications in 1400 and was later (by 1415) capital of the League of Chianti which were also part of Castellina in Chianti and Gaiole in Chianti, in 1478 it suffered destruction by the papal troops of the Duke of Calabria. Preserves the remains of walls and towers of the ancient walled city and the medieval urban structure plan stretched elliptical. At the center of town, the great palace of the Podesta, decorated with coats of arms on the facade.


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