Castiglion del Bosco, A Rosewood Hotel
Montalcino, Italy
★ Verified by our editors · June 2026
The verdict
A 5,000-acre Brunello wine estate in the heart of the Val d'Orcia, wrapped around a restored medieval borgo and run by Rosewood. 42 suites and 11 private-pool villas, a Michelin-starred restaurant, a proper Brunello di Montalcino winery, Italy's only private golf club and a spa — spread across cypress-lined hills that are UNESCO-listed for a reason. Large and polished, but the setting and the wine make it one of the great Tuscan stays.
Wine lovers and families who want a full-estate Tuscan stay with a Michelin table and a serious winery.
You want something small and hidden — this is a vast, five-star estate, not an intimate farmhouse.
Book a villa with its own pool over a suite, tour and taste at the Brunello winery, and reserve Campo del Drago (the Michelin table) at least one night.
The rooms
42 suites in and around the restored medieval borgo — antique furniture, exposed beams and warm Tuscan tones — plus 11 villas with their own gardens, kitchens and private pools, scattered across the estate. The villas are the ones to book for space and seclusion.
The setting
In the heart of the Val d'Orcia near Montalcino, a UNESCO World Heritage landscape of cypress hills and vineyards. The 5,000-acre, 900-year-old estate holds its own Brunello di Montalcino winery, a golf club, a cooking school and castle ruins — you rarely need to leave.
The food
Two restaurants: the Michelin-starred Campo del Drago for contemporary Tuscan cooking built on estate produce, and the more relaxed Osteria La Canonica in the old borgo. The wine list, unsurprisingly, is deep in Brunello.
Getting there
About 1h30 from Florence and Pisa airports and roughly 40 minutes from Siena, down a long white gravel road into the estate. A car is essential out here — the Val d'Orcia is made for slow driving.
Good to know
This is a large estate rather than a boutique bolt-hole; it can host weddings and events. Best for those who want to settle in for a few days and use the winery, golf, spa and restaurants. Open roughly spring to autumn.
