Rosewood Castiglion del Bosco is a restored medieval estate in the heart of Tuscany's Val d'Orcia, a UNESCO World Heritage Site. The Tom Weiskopf-designed course is the only private golf club in Italy, winding through 4,200 acres of vineyards, olive groves, and centuries-old forests with views of the Brunello di Montalcino region.
42 rooms · 1 course · Europe
At 685 yards from the tips — among the longest par 5s in Europe — the 13th drops steeply downhill through the UNESCO-listed Val d'Orcia landscape. A large bunker guards the right side of the fairway, a cross bunker threatens at 350 yards, and two flanking traps protect an approach green that seems to invite aggression the gradient never quite delivers.
Set on a 5,000-acre private estate in the Val d'Orcia UNESCO landscape outside Montalcino, Castiglion del Bosco combines a Tom Weiskopf-designed golf course, a Brunello di Montalcino winery, and a medieval borgo of restored 17th- and 18th-century farmhouses. The 42 suites and 11 private villas each include a Land Rover Defender for…
The Club at Castiglion del Bosco is an 18-hole course co-designed by Tom Weiskopf and Phil Smith in 2012 — Weiskopf's only design on the European continent. The layout traces the soft hills and valleys of the estate with panoramic views across the Val d'Orcia, reserved exclusively for members and…
The estate operates one of the historic Brunello di Montalcino production estates, with vineyard tours and wine-tasting seminars conducted on-property. Signature spa treatments — including the Tuscan Wine Embrace Ritual — are built around the estate's grape harvest, and Ristorante Campo del Drago…
Housed in the estate's original wine cellars, the spa offers four treatment rooms, sauna, steam bath, relaxation area, and a private garden. Treatments are built around Officina Profumo Farmaceutica di Santa Maria Novella and Evidens de Beaute, including the signature Tuscan Iris Embrace and Tuscan…
Osteria La Canonica · Campo del Drago
Spa · Pool · Winery & Wine Tastings · Cooking Classes · Truffle Hunting · Horse Riding
April - June, September - November
Tuscan spring brings wildflowers across the Val d'Orcia, while autumn delivers harvest, truffle season, and the cool mornings that make the Weiskopf course play its sharpest.
Book a truffle hunting excursion in autumn — you'll walk the Val d'Orcia with a local truffle hunter and his dog, then the kitchen will prepare your finds that evening. The on-site Brunello di Montalcino winery rewards an entire afternoon of deliberate tasting, particularly after a round on the course that cuts through the same estate vineyards.
Private equity golf club (invitation only)
Start the full applicationHelicopter transfers from Florence or Rome can be arranged through the concierge; each private villa includes a dedicated Land Rover Defender for estate exploration.
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