At Rosewood Castiglion del Bosco, immerse yourself in a woodsy lifestyle where Tuscany’s finest offerings—winemaking, natural beauty, fresh cuisine, and rich history—blend seamlessly. Set within the UNESCO-protected Val d’Orcia region and along the historic Via Francigena pilgrimage route from Canterbury to Rome, this expansive 5,000-acre estate is steeped in 800 years of history.

In 2003, Massimo and Chiara Ferragamo, heirs to Italy’s legendary fashion dynasty, acquired the property with plans to produce Brunello di Montalcino wines, only to discover they had inherited much more. The couple transformed the estate from a borgo—complete with a medieval church and castle ruins—into a resort, while honoring its origins and celebrating Tuscany's timeless charm.

When it became Italy’s first Rosewood property in 2015, the deep connection to the land became even more prominent. Restored farmhouses and a picturesque row of historic buildings provide the infrastructure, but the heart of this luxury resort lies in its breathtaking landscape.