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During the Middle Ages Gaiole in Chianti was an important market place, developed along the road for Valdarno. The numerous castles and parish churches in the vicinity bear witness to an intense and prosperous activity. Among the castles, which were all established in the Middle Age, of particular interest is Vertine, also Meleto with its two majestic rounded angular towers, Barbischio, Spaltenna and above all Brolio castle.
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