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Southeast of Siena, not far from the Umbrian border, the towns of Montepulciano, Montalcino, and Pienza are Tuscan classics—perched on hills, constructed during the Middle Ages and the Renaissance, and saturated with fine wine. Venture farther south and you encounter Tuscany with a rougher edge: the Maremma region is populated by cowboys, and a good portion of the landscape remains wild. But you won't forget you're in Italy here; the wine is still excellent, and some locals store their supply in Etruscan tombs.
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