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The city's origins go back to Etruscan times of which there are many visible remains to explore both in the excavations at the well marked archeological sites and in the Archeological museum in the city center.
Salingolpe, as it was known in the early Middle Ages, was given as a fief by Matilda of Tuscany in the 11th century to the powerful Count Guidi family.
In the mid 1200's the "Lega of Chianti" was formed as a governing body and Castellina, Radda and Gaiole were the sole participants. Eventually, the Florentines turned it into an important stronghold due to its strategic position between Florence and Siena, of which today the Rocca still remains.
The town was destroyed and rebuilt many times during the battles between the two poweful cities from the north and south, and every time the town was reconstructed, they made bigger defensive walls.
Legend has it that even Brunelleschi was asked to work on the project of new walls for the town.
The City Center:
The borgo still preserves the quadrilateral shape of the ancient medieval fortification and reminders of the many towers that once protected it from invasion during the period of conflict between Florence and Siena can be seen incorporated into some of the modern architecture. The main fortification, called the Rocca and its huge 14th-century tower, has a magnificent view over the town and the surrounding countryside. It is a stunning venue for civil wedding ceremonies or events.Along the ancient walls there lies an impressive underground tunnel now called Via della Volte which is lined with shops, artisans and restaurants. The tunnel itself goes around the city, enclosing the city center from below and it makes for a cool and refreshing escape from the summer sun. It was once an open air road and as the city felt the need to expand, it built over the road creating a “tunnel”. This unique formation is divided by the main street, Via Ferruccio which houses more boutiques, workshops, cafes and important buildings.
Churches and Museums:
The Church of San Salvatore deserves a visit. It was rebuilt in 1945 after the devastation of WWII, but still displays a valuable fresco by Lorenzo Bicci depicting the Virgin Mary with Child and a wooden statue from the Renaissance.
Inside the Rocca is the headquarters for the local commune or Municipality and the Archeological Museum of Chianti, displaying important archeological findings from the surroundings that testify to the ancient origins of the Chianti region. The museum is divided into three themes, and the artifacts focuses on the Bronze age finds, those of the nearby Etruscan excavations and the medieval structure of the city. There are also several exhibits of pieces from neighboring digs and is suitable for all ages, with interactive learning tools.
Nearby:
Fonterutoli
According to the legendary tale of how the borders in Chianti were created, it seems that the race between the Florentine and Siena horseman, ended right here in this area between Fonterutoli and Castellina: Crocefiorentina.
The estate has been in the Mazzei family since 1435, and very little has changed in its appearance since then except for the family villa and the production of excellent wines. Located just ten minutes south in the direction of Siena, this area is often included in biking and hiking itineraries. In addition to great views and wine, you will also find the archeological dig of Poggino di Fonterultoli, and 5 tombs dating in the 6th century. The museum displays the artifacts found here.
Montecalvario
Within walking distance of the city center, this Etruscan tomb is open to the public. The tomb dates from the sixth century BC and has four burial chambers oriented north, south, east, west, and each consisting of a main burial room and lateral cells. The tomb was discovered in the 16th century but since it was not properly excavated in the early 1900’s much of the valuable artifacts were looted. Perhaps the most exciting find, are the remnants of the “carro” or Etruscan carriage which has been reconstructed and visible in the Museum in Castellina.

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