Culture & Design: 15th C. Tuscan Villa, Siena, Italy

Even now, the approach to the 1,200-acre property is just as it must have been centuries ago: a long, winding ride through pale, undulating fields, leading to a dignified hilltop retreat. The three-story ivy-wrapped building is ringed by 20-foot obelisk-like cypress trees — a private citadel entered through a wrought-iron gate. Beyond the vista of olive groves, another fortresslike outcropping is visible in the distance: the mottled russet city of Siena, three miles away.

WHEN RENÉ CAOVILLA, the 82-year-old Venetian shoe designer, was first shown the Tuscan villa he bought in 1977, he fell in love with it instantly. He wasn’t only taken with the house, a 15th-century red brick monastery that had undergone a slow transformation into an austere 20-bedroom private home in the 17th century, but the Chianti landscape as well — the whole of classical history evoked in a flash.

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