Tuscany · Italy
JESSICA & MATTHEW
09 · 08 · 2026
The piazzetta at Castiglion del Bosco — cobbled stone, canopied tables, and cypress-covered hills rising behind the borgo.
Rosewood · Val d'Orcia, Tuscany

A restored medieval borgo in the hills of Montalcino.

Castiglion del Bosco is a private 5,000-acre (2,000-hectare) estate in the hills of Montalcino, in southern Tuscany. At its centre sits a restored medieval borgo — a walled village of stone houses, a small piazza, and a Romanesque chapel — abandoned for centuries until the Ferragamo family began its restoration in 2003.

The estate sits entirely within the Val d'Orcia, recognised by UNESCO as a World Heritage site in 2004 for a cultural landscape essentially unchanged since the Renaissance. This is the Tuscany most people picture when they picture Tuscany: cypress-lined lanes, rolling wheat fields, and hilltop towns — Pienza, Montepulciano, San Quirico d'Orcia — all within half an hour by car.

Castiglion del Bosco is also one of the historic estates of Brunello di Montalcino, Italy's most protected red wine region, with working vineyards, a cellar, and olive groves spread across the rest of the property. The surrounding land is forest and open pasture; there is no through-road and no town inside the gates.

The effect is seclusion without isolation — a self-contained estate, an hour and three-quarters from Florence and ten minutes from Montalcino, surrounded on all sides by protected countryside.

RegionVal d'Orcia, SI
Nearest AirportFlorence (FLR)
Drive from Florence≈ 1h 45m
Nearest TownMontalcino