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Spread along a narrow ridge, Montepulciano is one of Tuscany’s highest hill-towns. On main transport routes from Siena and Florence, it makes a fine touring base. Foremost among a medley of photogenic palaces and churches within its ancient walls is the exquisitely proportioned Madonna di San Biagio. The region’s Vino Nobile wine draws many visitors, as does its July jazz festival and a barrel race through the streets in late August.