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Gaiole's sights are castles and an abbey, and almost all of them are outside the town.

Castello di Brolio is the one with national consequences. The Ricasoli seat since the twelfth century, the last Florentine outpost on the Sienese border, sacked in 1478 after bombardment, rebuilt, and remade in 1835 as a brick English manor. In 1874 Bettino Ricasoli defined here the blend that the Chianti Classico rules later followed.

The Badia a Coltibuono is the oldest. Founded in 1049, in Vallombrosan hands by 1115, one of the richest monasteries in the region, suppressed under Napoleon in 1810 and then passed through a lottery, a Polish prince and a succession of creditors before becoming the wine and oil estate it is now.

Castello di Meleto keeps a theatre. A quadrilateral around a central cassero tower, with two cylindrical bastioned towers added after 1480 on the exposed southern side, rooms furnished and frescoed to eighteenth-century taste, and a teatrino with seven original Settecento stage sets.

Vertine is the intact borgo, first named in a private document of 1013, Ricasoli property from 1202, and still enclosed in its walls with its cassero and one surviving gate.

And the Pieve di Santa Maria a Spaltenna is the fortified parish church, to which the pieve of San Pietro in Avenano was transferred between 1102 and 1110.