Rosewood Castiglion Del Bosco is the brand’s only Italian property. Massimo Ferragamo’s historic Tuscan estate, set across a lavish 4,500 acres just 30 minutes from Siena, encompasses an entire village and network of farms into suites and villas done in a luxury style only Rosewood and the Ferragamo name can achieve.

It’s hard to need a “reason” to travel to one of Italy’s most beautiful regions, but if you do — here are 7 to make you want to book a trip, rightthisverysecond. 

The Vendemmia, or Grape Harvest

Castiglion del Bosco is also a historic winery and the fifth largest producer of Brunello di Montalcino, grown on 51 hectares of its vineyard. The on-site winery hosts an array of wine-making and wine-tasting seminars, and an annual harvest festival takes place in October. Take part in one of two Fall Harvest Experiences that allow guests to immerse themselves in the estate’s deeply rooted wine-making traditions, from vine to barrel, as well as a number of wine-tasting and pairing experiences.

Hunt for truffles

Famous for their aroma and taste, truffles are the jewels in Italy’s gastronomic crown and the fall brings peak truffle hunting, cooking and savoring season.  Visitors can take part in a memorable truffle hunt accompanied by local experts and their highly trained dogs.  During the last three weekends in November, guests can visit the “La Sagra del Tartufo Bianco (White Truffle Fair) in San Miniato, and explore the large offering of truffles and truffle-derived products, wine, pecorino, salami, olive oil, grappa and more.

Olive Oil Harvest

Autumn is a magical time to visit Tuscany and the Olive Oil Harvest is an unforgettable experience.  This fall, learn how to pick the olives, savour the authentic taste and discover all the secrets of the Tuscan extra-virgin olive oil at Rosewood Castiglion del Bosco.  The resort also offers a guided tour of a local olive mill situated in the heart of Val d’Orcia, foiled by an oil tasting.

Go to ‘Feast of the Thrush’

The Sagra del Tordo (Feast of the Thrush) festival takes place on the last weekend of October in Montalcino.  The spectacular event is open to the public and includes drum parades and archery trials on Saturday, and a popular feast held inside the walls of the castle all day Sunday.

Enjoy Mushrooms and Chestnuts

For centuries chestnuts were a staple food of much of the Tuscan region.  Today many villages still celebrates the fall season with special dishes made with this fruit and amazing festivals.  Visit the charming village of Vivo d’Orcia for the annual Sagra del Fungo e della Castagna (Mushroom and Chesnut Festival), which takes place the second and third weekends of October and offers an impressive variety of porcini mushrooms and chesnuts.

Play Golf

The cooler fall months are ideal for golfers traveling in Tuscany.  Rosewood Castiglion del Bosco’s beautiful 18-hole golf course (the only private golf club in the country) was designed by legendary British Open winner Tom Weiskopf.

 Learn to Cook

Take a cooking class at Rosewood Castiglion del Bosco’s very own La Canonica Cooking School.  Using fresh, seasonal ingredients from the on-property garden to make themost traditional and beloved Tuscan fare, such as fresh pasta and Italian pizza.  La Canonica Cooking School also offers classes focused entirely on vegetarian dishes, vegetable gardening, and the full Tuscan meal experience, so that guests can learn not only how to make Italian dishes, but also how to properly prepare the dishes a day in advance and focus their hosting efforts on their guests the following day.

Villa Sant'Anna. Castiglion del Bosco

Villa Sant’Anna. Castiglion del Bosco