5. Villa Machiavelli
Glynn Cohen, a South African investor, might live in Monaco, but his heart is at Villa Machiavelli (also known as Villa Mangiacane), a Tuscan estate halfway between Florence and San Casciano. In 2000 he bought this 27-room home, situated on 600 acres, and set about restoring it.
The property was designed by Giorgio Vasari the Younger for the uncle of Niccolò Machiavelli (author of The Prince), but had fallen into serious disrepair. "The previous owner had lowered the ceilings, divided it into apartments, and drilled holes into frescoes," says Cohen. Though he originally intended to have exclusive use of the place year-round, "I just wasn't spending enough time there, and it felt a shame that other people couldn't enjoy it."
For the first time in 400 years, guests are welcome to pass through the gates--guarded by large sculptures of snarling dogs and a (real) chocolate Labrador--to enjoy the historic estate, which boasts its own winery and olive press, 100 acres of vineyards, and miles of winding Etruscan trails.
It also has some touches not around in Machiavelli's day: two pools, a spa designed by Cohen's fiancée, Nadiia, a collection of modern sculptures from Zimbabwe, and a recent gift he bought for his fiancée and daughter: two miniature horses.
San Casciano Val di Pesa, Italy
26 rooms, from $410 to $3,535 a night wimco.com 
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