Castiglion del Bosco, A Rosewood Hotel

Rosewood Castiglion del Bosco sits within the UNESCO-listed Val d’Orcia near Montalcino, occupying one of Tuscany’s oldest and best-preserved agricultural estates.

The 5,000-acre property is centered on a 900-year-old borgo with castle ruins and a medieval church, while restored farmhouses and newer guest spaces spread across the surrounding countryside.

Accommodation includes suites within the village and substantial private villas converted from historic farmhouses, many with pools and fully residential layouts designed for longer stays.

The estate operates its own Brunello di Montalcino winery, cooking school and organic garden, while a private 18-hole golf course and spa give the property a level of recreational depth rare in Tuscany.

Castiglion del Bosco is best for travelers who want wine country at its most complete and private, where food, golf, history and landscape are all part of a single estate experience.