Step Into The Rosewood Castiglion del Bosco

Castiglion del Bosco is one of the best preserved estates in Tuscany.
Rosewood Castiglion del Bosco pool

This post was produced in partnership with Rosewood.

Nestled in the countryside of the Val d’Orcia, with enviable views of cypress trees and the lush forests below, Castiglion del Bosco is one of the best preserved estates in Tuscany and among the finest properties in all of Italy. The 800 year old borgo spans 4,000 acres and combines natural beauty and history with warm hospitality and world-class service, making it the perfect place for a luxurious countryside escape.

The Val d’Orcia is a UNESCO World Heritage Site known for its charming hilltop towns and grand vistas: this is “Tuscany at its Tuscaniest” and remains celebrated for strong local traditions and an agrarian heritage. The Val d’Orcia has come to symbolize harmony with nature so Italians and travelers alike flock to these verdant valleys for a change of scenery from the country’s buzzing metropolises. With rustic architecture, manicured vineyards and relaxed pace of life, the region is a perfect backdrop to live out your own holiday Under The Tuscan Sun.

Founded by Massimo and Chiara Ferragamo and managed by Rosewood Hotels and Resorts, this world-class resort is effusively idyllic and elegant – a perfect emblem of Tuscan lifestyle and rustic charm. It caters to an affluent clientele and boasts Italy’s only private golf club along with a historic winery that is the fifth biggest producer of highly acclaimed Brunello di Montalcino.

The property is centered around the historic Borgo which has a townhouse with cozy suites, an organic kitchen garden, spa, infinity pool and fitness center – as well as two restaurants, a rustic Osteria La Canonica which also offers cooking classes and the more upscale Ristorante Campo del Drago. You’ll have the chance to taste Tuscan Panzanella, Truffle Pizza, Tagliatelle with Porcini Mushrooms and other classic dishes of the region, accompanied by local wines (more on those below).

The Rosewood Castiglion del Bosco also has 14 private villas that guests can rent. These rustic farmhouses have been converted into luxury properties and are dotted around the estate: they can sleep anywhere from 2 – 14 people, with multiple bedrooms, outdoor living areas, guesthouses and more. Each villa has its own private heated infinity pool that overlooks the splendid landscape below and some even have tennis courts and a home theater. And with handsome interiors and bespoke furniture, you’ll feel truly pampered during your stay.

A short drive from Montalcino and Pienza, and only one hour from Siena, it’s also a great location for enjoying nature and exploring the small towns of the Val d’Orcia. There are plenty of activities to keep you busy, from cooking classes and wine tastings to cultural visits and bike rides through the Tuscan countryside. The region is replete with vineyards that produce Super Tuscan wines which you can try during a a winery visit.

Castiglion del Bosco Winery

The Castiglion del Bosco winery produces a number of quality wines and it is the fifth largest producer of Brunello di Montalcino, one of Italy’s premiere red wines and the first to be awarded the coveted DOCG designation (Denominazione di origine controllata, or controlled designation of origin). Brunello, which has a rich, red hue, has moderate tannins and fragrant berry notes that pairs it well with hearty Tuscan fare, red meats and tomato-based dishes.

During a tour, you’ll visit the 2,000 hectare vineyard and head inside the cellar where wine ferments in French oak barriques and barrels before being aged in bottles for 6 to 36 months. The tasting is accompanied by Tuscan cheeses and cold cuts served with fresh bread, extra virgin olive oil and locally-produced honey. You can also opt for a Brunello vertical tasting to try six Brunello di Montalcino vintages. Whatever experience you choose, don’t miss a chance to peek into the Millecento Wine Club, one of the most exclusive wine clubs in the world where enophiles and celebrities keep their most prized bottles.

Castiglion del Bosco is a family-friendly property that offers landscape painting classes and archery lessons for children as well as group cooking experiences. Be sure to mark your calendars for the sensational Palio Horse Race that takes place twice a year in Siena in early July and mid August or come in the fall for the olive harvest or Vendemmia, where you can pick Sangiovese grapes from the estate’s vineyard and see up the production of Brunello di Montalcino up close.

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