Rosewood Castiglion Del Bosco

An ancient village in the Sienese countryside transformed into a luxurious resort, the Rosewood Castiglion Del Bosco is a beautiful property full of Tuscan charm and hints of history, all wrapped in a stunning setting on over 4,500 acres of land. Comprising several 800-year-old stone buildings that have been beautifully restored, some covered with enchanting ivy, the place evokes another time; the ancient "borgo" (town) is set within a scenic Val d'Orcia landscape of gorgeous countryside, hills, vineyards, and meandering cypress-lined roads. There is a central cluster of buildings in the center of the property -- including the original castle, the winery, and the stables -- now housing the 23 suites, the restaurants, the reception area; there's even a chapel. There are also old stone farmhouses on the grounds that are now operate as villas. The pool and restaurants face rolling countryside, while other parts of the property face forested hillsides. Impeccable interiors are a mix of traditional and contemporary style, with elegant, Tuscan-inspired decor and historical touches like original fireplaces and oil paintings on the walls. The inviting drawing room (in a separate building from the more unassuming reception area, located next to the restaurants) is awash in cream and ochre hues and has the feel of an upscale living room, with beautiful chevron wood flooring, an undulating ceiling, handsome furniture, area rugs in rich hues, and floor-length curtains framing windows that fill the space with sunlight. Elegant seating includes plush striped sofas cozily arranged in front of an old fireplace, as well as chic, classic armchairs throughout.It's no surprise that the property was founded by Massimo Ferragamo, son of the famed designer, as an eye for design and attention to detail are easily apparent. The property is now managed by Rosewood Hotels & Resorts, and attracts a well-heeled clientele that includes couples on romantic getaways, as well as families and groups drawn by the spacious private villas. Most guests spend their days exploring the surrounding area, wine tasting, participating in one of the many on-site activities (such as cooking classes), or in warmer months, lounging by the pool. 

Situated in Tuscany's Val d'Orcia region, the property occupies gorgeous, sprawling grounds in a scenic, quintessentially Tuscan setting of green hills, vineyards, and cypress-dotted countryside. It's a bit isolated and a car is necessary to get around. The road approaching the property is one of the area's so-called "strade bianche," or white roads, named for the white gravel covering them; the main thing to be aware of is that this road is unpaved and uphill, so your rental car may get a little roughed up. There are restaurants and wineries in the area, as well as a winery on-site (it's worth doing the tour). The lovely ancient hilltop town of Montalcino, famed for its Brunello di Montalcino wine, is a 23-minute drive away, while Buonconvento, where guests will find a train station, is 17 minutes away. Siena is about 50 minutes away, while the seaside can be reached in about an hour-and-a-half. Other popular destinations include the towns of Pienza (45 minutes away), Montepulciano (one hour away), and Cortona (an hour-and-a-half away). Florence and its airport is approximately two hours away.

The hotel has 23 spacious suites as well as nine gorgeous villas housed in restored stone farmhouses. These luxurious spaces feature elegant, classic decor with a touch of countryside charm, and include antique furniture, fine fabrics, and a tasteful Tuscan-inspired color palette of ochre, sienna, or forest green shades pared with creamy neutrals. Many rooms have beautiful chevron wood flooring, and some also feature exposed wooden ceiling beams. Four-poster beds in some of the rooms are elegant and romantic, while beautiful oil paintings, handsome antique pieces like writing desks, and old stone fireplaces add a touch of history. Windows offer gorgeous views over the surroundings, and some suites have large, private furnished terraces with stunning vistas. Some are of forested hillsides rather than the rolling countryside, but most will find either outlook lovely. Some suites have sitting areas, but most have separate living rooms as well as large walk-in closets. The two-bedroom Villa Suite has a kitchenette and a large private garden. The luxurious private villas offer a bit more privacy and sleep from six to 12 guests. They're surrounded by beautiful gardens and enjoy an array of features -- including private heated outdoor pools. They have full kitchens, living and dining rooms, laundry facilities, and gorgeous outdoor areas to relax in and take in the views. Some even have outdoor wood ovens, private tennis courts, and theater rooms.Standard amenities include large flat-screen TVs, electric kettles, Nespresso machines, minibars, electronic safes, iPod docks, and free Wi-Fi. Bathrooms are large and feature luxurious rustic charm, equipped with both soaking tubs and separate walk-in rainfall showers, as well as bidets, double sinks, and all the requisite little luxuries like high-end toiletries, magnifying mirrors, and plush robes.

One of the highlights here is the hotel's beautiful outdoor infinity-edge pool, which offers gorgeous views over the scenic green landscape that unfolds around it. It's surrounded by a large stone sundeck with umbrella-shaded padded loungers, and there's a poolside bar that serves drinks and food.Two on-site restaurants offer delicious Tuscan fare and Italian classics. Osteria La Canonica is the more casual option, and is open for lunch and dinner. The Ristorante Campo del Drago offers a fine-dining experience, serving classic Italian fare with produce culled from its own organic kitchen garden; it's open for breakfast and dinner. Alfresco dining options are available at both, with stunning views over the surrounding countryside. There's also a cozy bar with a lovely terrace where guests can enjoy some of the famed Brunello di Montalcino wine as well as light bites. Rooms service is also available. Though the food is excellent, note that prices are steep. Other culinary experiences include classes at the on-site cooking school, as well as tastings, tours, and other events at the hotel's winery, which is the fifth-largest producer of Brunello di Montalcino.Situated in the former wine cellars, the hotel's spa offers a menu of La Prairie treatments, as well as a sauna, steam bath, and lovely garden where guests can relax. The glass-walled fitness center is well equipped and offers views over the beautiful Tuscan landscape. Yoga and Pilates classes are also available.The hotel's sprawling grounds are also home to an 18-hole golf course and a Club House with a bar, pro shop, and practice facilities. Other on-site amenities include a free kids' club that offers a variety of activities for children (some activities/events are charged extra), horseback riding, and meeting and event space -- including wedding services.