montefiridolfi-chiantiTo reach the castle and church of Montefiridolfi, turn left at a modern tabernacle just before the piazza. The lords of Montefiridolfi originated from the Buondelmonti family. From the early 13th century the place was said to belong to the “figli di Rodolfo” then Firidolfi, descendants of Ridolfo de’ Buondelmonti, the castle’s 12th century owner. Of this ancient manor house, which dominated the Pesa valley, only a few traces of the walls remain. Behind the castle is the Church of Santa Cristina, built by the Buondelmonti, possibly before the 12th century. It has a simple facade with a pediment which is the result of later restorations. Inside, in the left chapel, is a Madonna and Child with Saints ]ohn the Baptist, Christina, Jacop and Biagio. The panel, painted in 1513 for the priest Jacopo Bambagini is attributed to the Maestro di Marradi, a painter influenced by Botticelli and Ghirlandaio, active between the late 15th and early 16th centuries.

Via di Bibbone Starting at Montefiridolfi, via di Bibbione winds on the levelled hilltops above the right bank of the Pesa until it reaches the Castle of Bibbione. From here, it dips down with sharp bends to the river, and meets the via Cassia between Calzaiolo and Bargino. The road crosses an area densely cultivated with vineyards and olive groves, passing three churches and several farms and villas. Almost all of these buildings date to Medieval times when the whole area was the dominion of the Buondelmonti. It was
these properties, together with the castles of Fabbrica and Bibbione on this side of the river, and the Castle of Pergolato on the opposite side, which gave the powerful Florentine family their long reign over the Pesa river and the via Romana.

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