The road from Radda leads towards the pass over the Monti del Chianti,
via Gaiole in Chianti. Gaiole, important customs post and market location
on the way to Siena, today is site of numerous fairs and festivals.
The Settembre Gaiolese, for example, in September is a major wine fair.
There are several major producers, castles and farm estates, in the
Gaiole area, some of them very important in historical terms as well
as in the wine field. On the road from Gaiole to Siena is the historic
Brolio Castle, residence of the Ricasoli family since the Middle Ages,
whose 19th-century scion, Baron Bettino Ricasoli was Lord President
of the Council several times after the Unity of Italy (1860).