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Castellina's sights divide cleanly into three ages, and the town is small enough to see all three in a day.

The Etruscan layer is the oldest and the most surprising. The tumulo di Montecalvario, over fifty metres across with four chambers on the cardinal points, and the necropoli del Poggino near Fonterutoli, where four monumental tombs are linked by a woodland path, both belong to the 7th–6th century BC. Both were robbed long ago; what they still have is their architecture.

The medieval layer is a single building and a single street. The Rocca β€” Florence's fortress, begun in 1401, the municipio until 2006 and now the Museo Archeologico del Chianti β€” and the Via delle Volte, the vaulted wall-walk that is all that remains properly of the circuit.

The third layer is what came back after destruction. The chiesa di San Salvatore was rebuilt in neo-Romanesque form after the last war and holds a Madonna with Child of disputed attribution and the body of San Fausto, patron of the Chianti. And Fonterutoli, down the Chiantigiana, carries the legend that gave the region its black cockerel.