Rosewood Castiglion del Bosco
Expect a woodsy way of life at Rosewood Castiglion del Bosco, where Tuscany’s fine trappings — winemaking, natural splendor, fresh food and multilayered history — harmoniously come together. Part of the UNESCO-protected Val d’Orcia landscape, just off the Via Francigena pilgrimage route from Canterbury toward Rome, the vast 5,000-acre estate has 900 years of history behind it.
Massimo and Chiara Ferragamo — as in Italy’s top fashion family — snatched up the property in 2003 when they were seeking a space for producing Brunello di Montalcino wines and got more than they bargained for. The couple transformed the estate from a borgo (a village, complete with a medieval church and castle ruins) into a resort, preserving its origins and celebrating everything Tuscany is known for.
When the estate became Italy’s first Rosewood-branded property in 2015, these place-centric details became even more pronounced. Restored farmhouses and a charming strip of historic buildings make up the infrastructure, but the lifeblood of the luxury resort is the landscape itself.
- Run by executive chef Matteo Temperini, the elegant Ristorante Campo del Drago serves gourmet twists on traditional Italian cuisine.
- In a similar fusion of international and regional, The Spa at Rosewood Castiglion del Bosco offers treatments and products from Florence’s beloved Santa Maria Novella pharmacy.
- The Club at Rosewood Castiglion del Bosco is home to an exclusive gathering house and Italy’s only private 18-hole greens, dreamily designed by former-golf-pro-turned-architect Tom Weiskopf. Hotel guests enjoy privileged access to The Club, with a limited number of reserved tee times, subject to availability. A golf handicap certificate is required.
- The Montalcino hotel’s main infinity pool looks like part of the landscape, its sandstone-colored deck blending in seamlessly with the surrounding vegetation.
- Seasonal dishes made with vegetables hand-picked from the garden pair well with Val d’Orcia views at Osteria La Canonica, an unfussy spot for all-day dining.
- Be prepared for an adventure getting to the property; you’ll wind your way up a dirt road alongside wild-boar- and deer-dotted woods. There’s a level of countryside remoteness that’s great if you are looking to get away.
- You can streamline your gift and souvenir shopping with a visit to the luxury hotel’s charming boutique, which sells a range of regionally made clothing and crafts.
- Learn authentic Tuscan cuisine by taking a class at the hotel's La Canonica Cooking School, named for its location in what was once the village rectory.
- Oenophiles will be in heaven here — the luxury resort boasts its own on-site winery producing rich, red Brunello di Montalcino vintages. The winery hosts an array of seminars and tastings, but visit in September to take part in its annual harvest.
- Whether you book a roomy suite on the main site or prefer the privacy of one of the 11 secluded villas spread throughout the property, expect to find curated touches in your sleeping quarters. Much of the décor was produced by area artists and artisans.
- Suites have a homespun feel, with décor in distinctly Tuscan shades (olive green, deep red and gold) and textiles sourced from Florentine producers. Most have ample seating areas and antique furniture.
- For an ultra-luxurious home-away-from-home, the hotel's villas don't disappoint. Ranging from three to six bedrooms, these sprawling retreats each boast their own personality, from the romanic Villa Alba perched on a hilltop to the historic Villa Castello and super sumptuous Villa Oddi with its home theater and private tennis court.
- Rosewood Castiglion del Bosco is more child-friendly than many comparable properties, with a complimentary Kids Club to keep little ones engaged (some fees may apply for specific events).
- All activities draw upon the Tuscan hotel’s spectacular natural environment and its resources — think cooking workshops, scavenger hunts and swimming lessons.
- If your kids are critter-crazy, they’ll get a kick out of seasonal visits to the estate’s farm, where they’ll have the chance to feed barnyard animals, including the regionally famous cinta senese pig.
24-hour room service 
Babysitting services
Bar
Fitness classes
Golf
Gym
House car
Meeting rooms
Outdoor pool
Pet friendly
Restaurants
Spa
Tennis
Rosewood Castiglion del Bosco has a private helipad on the estate. Helicopter charter and transfer service is available.
