Just 10 km from Montaione lies the medieval village of Castelfalfi with its castle and the beautiful Romanesque church of San Floriano.

Although the finding of an Etruscan tomb in 1926 in Podere Bianchi shows that the area was already inhabited in the Etruscan period, there was more relaying news about Castelfalfi from 754 AD, when the site was built by the Longobardo "Faolfi” from which comes the original name" Castrum Faolfi ".

The castle passed in 1139 to the bishop of Volterra and in 1230 he was submitted to San Miniato and then to Florence. In 1511 the Romanesque church of San Floriano was rebuilt and in 1554 the village was plundered by the militia of Piero Strozzi at the time of the war between Siena and Florence to become a holiday resort of the Medici-Tornaquinci family.

In the Renaissance period the Castle of Castelfalfi, situated on a rock spur overlooking the valley of the river Roglio, underwent various renovations until the transformation from a military manor to a villa, which has preserved its appearance until today.

Of particular curiosity are the cellars on two levels, where the first experiments of glazed tin can be found dating back to the beginning of the 20th century.

For a long time the village was supported by a predominantly agricultural economy until the early 1900s when it was built the “tabaccaia”  for processing the tobacco plants imported from America.

The territory of Castelfalfi is also known for an important finding of the 70s at the farm La Spina concerning the fossil remains of a whale (Balaena Montalionis), now kept at the Civic Museum of Montaione.

Recently, the Castelfalfi Estate has been restored and used as a tourist residence and with an elegant 27-hole golf course, set in a landscape of remarkable value.