Located near Gaiole in Chianti, Castello Di Meleto is a beautiful 11th-century castle overlooking the Massellone Valley. The castle is said to have belonged to a group of monks of the nearby Badia a Coltibuono in the 11th century and was later entrusted to the Di Meleto branch of the wealthy Firidolfi family. The strategic location of the castle near the border of Sienna and Florence meant that it was often the scene of violent encounters between various rivalling factions over the centuries.

In 1478 the castle was occupied by the Aragonese army, allies of Sienna, who added two large, cylindrical and machicolated towers near the southern end of the castle and on the northern end, two brick reinforcements were added. All these additions helped the castle to withstand a siege in 1529 by the imperial army. The castle was transformed and modified into a villa in the 18th century and up till today, the decor of the halls and theatre echo this bygone era.

Today the castle is owned by a wine-producing company whose vineyards stretches throughout the 1,400-acre property.