Next stop on the Chiantigiana is Castellina in Chianti (population 3,000). Just outside this trim medieval village on the Florentine/Sienese border there is an Etruscan tumulus (Montecalvario, seventh century). Castellina itself is dominated by its early 15th century castle. The parish church boasts a fresco by Bicci di Lorenzo, also 15th century.

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