If you only have time for one castle, visit the stunning Castello di Brolio. At the end of the 12th century, when Florence conquered southern Chianti, Brolio became Florence's southernmost outpost, and it was often said, "When Brolio growls, all Siena trembles." Brolio was built about AD 1000 and owned by the monks of the Badia Fiorentina; the "new" owners, the Ricasoli family, have been in possession since 1141. Bettino Ricasoli (1809-80), the so-called Iron Baron, was one of the founders of modern Italy and is said to have invented the original formula for Chianti wine. Brolio, one of Chianti's best-known labels, is still justifiably famous. Its cellars may be toured by appointment. There's a sign at the Brolio gate that translates as ring bell and be patient. You pull a rope and the bell above the ramparts peals, and in a short time, the caretaker arrives to let you in. The grounds are worth visiting, even though the 19th-century manor house is not open to the public. (The current baron is very much in residence.) There are two apartments here available for rent by the week.
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