Castello di Vicarello, Maremma
Rising in magnificent isolation on a rocky spur overlooking a verdant swath of the Maremma (Tuscany’s southern coastal strip), this 12th-century castle has been converted by owners Aurora and Carlo Baccheschi Berti into one of the area’s most stylish country hotels. A cultured house-party feel prevails—and if you rent the whole place, you get to choose who comes to the party. Or, indeed, to the hunting party: Berti has his own private 1,000-acre hunting reserve a 50-minute drive away, where several battute di cinghiale (wild-boar hunts) are organized each year. These are serious events: The dress code of the Tuscan-hunting aristocracy demands a shirt and tie be worn beneath that Barbour. Rentals start at $51,025 per week (sleeps 14); vicarello.it.