10 Reasons to Visit Tuscany in the Fall

I don’t need 10 reasons to convince me to visit Tuscany! The region in central Italy stole my heart a long time ago with its endless allure of great food, peaceful countrysides and talented artisans. I have a lot of great memories of my travels to the region with the family and without them. It’s why reading through this list of things to do and experience in Tuscany this fall has me drooling and dreaming. Whether you too have already mentally packed or are looking for some reasons to add it to your dream destination list, these reasons should help. Thanks to the team at Massimo Ferragamo’s historic Tuscan estate, Rosewood Castiglion del Bosco, for these 10 reasons to go now:

1.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. Castiglion del Bosco’s winery offers 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.

2. 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. A taste of mouth-watering truffles is enjoyed at the close of the hunt. The two-hour outing takes place 30 minutes from Rosewood Castiglion del Bosco. 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.

3. 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.

4. 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.

5. 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 chestnuts.

6. Play Golf

The cooler fall months are ideal for golfers traveling in Tuscany. Rosewood Castiglion del Bosco’s beautiful 18-hole golf course was designed by legendary British Open winner Tom Weiskopf. Set in a UNESCO World Heritage Site, it offers an unparalleled playing experience at Italy’s only private golf club.

7. Go Horseback Riding

Enjoy a breathtaking ride along the Sienese hills.

8. Paint a landscape

Take advantage of the gorgeous fall colors and capture the stunning natural surroundings of Castiglion del Bosco on canvas while enjoying a lovely day in the Tuscan outdoors. Landscape painting classes are led by two artist-instructors with many years of combined experience. Half-day mini courses are offered.

9. Try Archery

For archery enthusiasts or those interested in learning the sport, an archery field and all of the necessary equipment are available at Rosewood Castiglion del Bosco. Under the direction of an experienced teacher, guests can learn or practice this sophisticated interest. Instruction is offered for guests age six and up and sessions last approximately one and a half hours.

10. 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 the most 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.

Looking for more about Italy? Here are a few of my experiences:

The Time I attended Gelato University

Exploring Italy with Kids

Italian Food You’re Ordering Wrong in Italy