For the Sienese part of the itinerary we can start dall'Agriturimo La Selva 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 the Pesa. Its territory is entirely within Chianti Classico. The center of the most important of Chianti and a recreation area in constant development. Etruscan and Roman, fiefdom of the Nobles of Trebbio (XI century), was then an important Florentine military garrison. Capital of the ancient Chianti League with Radda and Gaiole in the thirteenth century, later, in the fourteenth and fifteenth centuries, Castellina was the scene of raids and looting. The Florentines encircle walls in 1400-1402. Dominated by the historic fortress, consisting of a defensive building high and topped by a keep even grander, it has medieval fortifications and whether, as the suggestive Via delle Volte. The town retains some of its character four-sixteenth. At 100 meters from the center of Castellina, along the road to Greve, there is a large Etruscan tomb dating from the sixth century BC, 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 district. Of particular value to those of San Martino Cispiano, which has preserved all its Romanesque grace, with a beautiful apse and nave, and San Leonino in Conio which holds a Madonna and Child by Lorenzo di Bicci. Rich in history is the village of Fonterutoli, already quoted in a document of 998. Near the village of Fonterutoli is the Necropolis of Poggino with the remains of some Etruscan tombs.
In the southern slope of the Chianti, 20 km from Siena, is Castelnuovo Berardenga which tells the name of its origins as a fortified village, situated on a hill between the Ombrone and the torrent Malena, in a ' area in traditional agricultural vocation still focused on wine production flanked craftsmanship of wrought iron. The castle, founded in the last area, which remains a tower and some ruins, was built in 1366 by the City of Siena with the intention of giving Castelnuovo functions of prominence on the territory of the Berardenga. In the town, a beautiful park surrounds the Villa Chigi Saracini. At nearby Pacina, remarkable the parish church of Santa Maria Maddalena, but remodeled medieval origins. Charming little fortified village of San Gusme, which remain the two original doors stone arched. In a lovely hilly area, at the heart of a beautiful valley, then it rises Vagliagli, with the adjacent castle of Aiola. In the municipal area stands out for the grandeur the Certosa, founded in 1343 and rebuilt in the second half of the `500.
Heading 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 capitals of the ancient Chianti League terziere, which were also part of Castellina in Chianti and Radda in Chianti. Just west dell`abitato, between woods and vineyards, there are two medieval fortified complexes: the parish church of Santa Maria a Spaltenna (first half of sec. XII) and the village of Vertine, recorded from the tenth century castle, surrounded by a walled perimeter of oval, with d`accesso door guarded by an elegant tower. Among the main attractions of the entire Chianti, Brolio Castle, home to one of the largest wine companies, it is among the first examples of bastion fort in the Tuscan area. Built by the Florentines, on pre-existing, after 1484, it has mighty polygonal enclosure, within which you have the vast palace of romantic style built in 1860 by architect Marchetti for Baron Bettino Ricasoli account. Other castles in the area, and those of Apple Orchard Cacchiano.
Radda in Chianti , set on a hill which marks the watershed between the valleys of the Pesa and Arbia. Today predominantly agricultural center (wine production) Radda boasts an ancient history: past by the counts Guidi in Florence in 1203, had fortifications in 1400 and was later (1415) the capital of the Chianti League which were also part of Castellina in Chianti and Gaiole in Chianti; in 1478 it was subsequently destroyed by the papal troops of the Duke of Calabria. Preserved remains of walls and towers of the ancient walled city and the medieval urban structure elliptical elongated. At the center of the town, the remarkable Palazzo del Podesta, adorned with coats of arms on the facade.