If you are like most people, you probably wouldn’t need much convincing to pack your bags and visit Tuscany. This lovely region in central Italy never fails to steal the heart of tourists with its talented artisans, serene countryside, and the irresistible allure of sumptuous delicacies.
Ask anyone who has already visited Tuscany and they will surely tell you all the great memories they had during their trips to the region either on their own or with their family and friends.
Whether you need a quick escape from the hustle and bustle of your everyday life or you are looking for a new dream destination to add to your list, here are five good reasons to travel to Tuscany in autumn:
1. Grab a Bite of Chestnuts and Mushrooms
Through the centuries, chestnuts were a favorite staple food in most parts of the Tuscan region. To this day, many villages continue to celebrate the autumn season with amazing festivals and a plethora of special dishes made with chestnuts.

Drop by at the pleasant village of Vivo d’Orcia for the Sagra del Fungo e della Castagna or Mushroom and Chesnut Festival held every year during the second and third weekends of October. The festival is the perfect time to delight in the variety of chestnuts and porcini mushrooms.
2. Join the Fun in the ‘Feast of the Thrush’
The Feast of the Thrush or Sagra del Tordo is a festival held in Montalcino during the last weekend of October. It is a spectacular event that welcomes everyone and includes archery trials and drum parades on Saturday. The following day Sunday, a famous feast is held within the castle walls all day long.

3. Embark on a Truffle Hunt
Truffles are popular for their taste and aroma, putting them on a pedestal as the true jewels of the gastronomic crown of Italy. The autumn season is the peak time to hunt, cook, and savor truffles at their finest.
Visitors can participate in an unforgettable truffle hunt together with the local experts accompanied by their highly trained dogs. At the end of the hunt, all participants can get a taste of the delectable truffles.

The outing that lasts for two hours is held just 30 minutes away from Rosewood Castiglion del Bosco. On November’s last three weekends, tourists can also visit San Miniato’s “La Sagra del Tartufo Bianco” or White Truffle Fair where they can explore huge offerings of truffles and a variety of products derived from it, as well as wine, pecorino, grappa, olive oil, salami, and more.
4. Experience Olive Oil Harvest
Autumn is the magical time for visiting Tuscany, and one of the most unforgettable experiences you can ever have here is none other than the Olive Oil Harvest.
Learn the right way of picking olives, relish their authentic taste, and explore the secrets of the extra virgin olive oil of Tuscany at Rosewood Castiglion del Bosco. There is also a guided tour in the resort where you can visit the local oil mill located at the very heart of Val d’Orcia with oil tasting to cap it off.
5. Participate in the Grape Harvest or The Vendemmia
The historic winery of Castiglion del Bosco is the fifth biggest Brunello di Montalcino producer cultivated on its vineyard that spans 51 hectares. The on-site winery offers numerous wine-tasting and wine-making seminars and a yearly harvest festival every October.

The winery of Castigliono del Bosco has two Fall Harvest Experiences where guests can immerse themselves in the deeply rooted traditions of wine-making of the estate from vine to barrel and other pairing and wine-tasting experiences.
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