As the crisp air of fall settles in, families across the U.S. gather for traditions passed down through generations. In Upstate New York, families head to orchards for apple and pear picking or spend weekends pumpkin hunting. Children race through fields, their faces lighting up with excitement as they choose the perfect pumpkin for carving jack-o’-lanterns or enjoy a fresh slice of apple pie à la mode. These are the cozy, comforting moments that make fall so special. It’s a season that brings people together in celebration of the harvest and the simple joys of life.

In Tuscany, we share this same reverence for the season. Our fall harvest traditions, like those in the U.S., are deeply rooted in family, land, and togetherness. Instead of pumpkins and apples, our bounty comes in the form of olives, grapes, truffles, and chestnuts—treasures of the land that we’ve harvested for generations.

This fall, I invite you and your family to experience the abundance of Tuscany in the fall firsthand. From olive picking to truffle hunting, Tuscany offers a unique opportunity to connect with our rich traditions while making unforgettable memories with your loved ones. 

A Local’s Guide to Experiencing the Fall Harvest in Tuscany with Your Family

Tuscany is an idyllic destination for families and friends seeking to experience the cultural richness of the harvest season. If you’ve ever dreamed of spending Thanksgiving in Italy, November is the perfect time to visit. Tuscany in the fall allows you to enjoy the region’s beauty without the crowds. The weather is pleasantly mild and incremental. Cooler temperatures make it ideal for outdoor activities like olive harvesting, truffle hunting, and wine tours. This time of the year offers an array of unforgettable experiences that honor the traditions of the land.

Here’s your guide to experiencing Tuscany’s fall harvest traditions with your loved ones, all tried and tested by our team:

1. Olive Harvesting and the Tradition of “Olio Nuovo”

In Tuscany, the olive harvest begins in late October and runs through November. This is when the much-anticipated olio nuovo (new oil) arrives. It’s the perfect activity for families who want to get their hands dirty and experience one of Tuscany’s oldest traditions.

Join local families as they rake olives from ancient trees and take them to the frantoio (olive mill). Here, the olives are processed into the season’s first oil. The fun begins when the olives are crushed into a fragrant brown paste. Soon after, a brilliant green liquid, almost neon in appearance, starts flowing from the machine’s spout. This fluorescent green color is a sign of exceptionally fresh, high-quality oil. It may look unusual, but this is exactly what authentic olio nuovo looks like!

Tasting Olio Nuovo the Tuscan Way

This oil is so prized that it’s celebrated at family feasts with nothing more than a slice of toasted bread, known as bruschetta. The bread is rubbed with fresh garlic and drizzled with the peppery, fruity olio nuovo. For an authentic Tuscan experience, gather your loved ones around a table. Dip fresh bread in the olio nuovo and savor the warmth of the season’s harvest.

While this tradition may sound simple, it’s a chance to slow down and appreciate the richness of the moment. Sometimes, true joy comes from something as simple as fresh olive oil on warm bread, shared with family.

Tip: Italians say, “olio nuovo, vino vecchio”: new oil, old wine. Unlike wine, extra virgin olive oil doesn’t improve with age. On the contrary, olio nuovo, the first oil of the season, is the most highly prized. If you’d like to bring some home, make sure it’s stored in metal containers and kept away from heat. Plastic and glass are not ideal for storage, as they allow light to degrade the oil’s quality.

2. The Grape Harvest: A Celebration of Tuscan Wine

The vendemmia, or grape harvest, is a centuries-old tradition that captures the heart and soul of Tuscany in the fall. If you visit between late September and early October, you’ll see vineyards across the region bustling with activity. Grapes are handpicked and transformed into some of the world’s finest wines, like Chianti and Brunello di Montalcino.

For families, this is the perfect time to visit Tuscany’s vineyards. Adults can enjoy wine tastings and vineyard tours. Meanwhile, children can have fun picking grapes straight from the vine or watching how grapes are turned into wine. Many vineyards offer family-friendly experiences, where kids can learn about the entire harvest process.

While traditional grape stomping is mostly a thing of the past, the essence of the vendemmia endures, offering a wonderful opportunity to connect with local winemakers and sample the fruits of their labor.

One of our newest villa rentals, Il Mulino dell’Abate, is the perfect home for wine lovers looking to experience the vendemmia in style. Nestled right next door to the Antinori nel Chianti Classico winery, awarded first place in the World’s Best Vineyards 2022 and The World’s Most Admired Wine Brand 2023, it’s the perfect location to enjoy the grape harvest up close. Guests staying at Il Mulino dell’Abate can immerse themselves in the nearby vineyard activities, making it an unforgettable place to be during this season.

Tip: Multiple wine festivals pop up in Chianti during the fall months. The main festival you shouldn’t miss is the multi-day Chianti Classico Wine Expo (Expo del Chianti Classico), which takes place in Greve in Chianti.

3. Truffle Hunting: Uncovering Tuscany’s Hidden Treasures

For families seeking a bit of adventure, there’s nothing quite like the thrill of truffle hunting in Tuscany’s autumn forests. The fall season is prime time for white truffles, one of the most coveted ingredients in Italian cuisine.

Accompanied by skilled truffle hunters, also known as cavatori, and their loyal dogs, you’ll venture into the woods in search of these aromatic fungi. The dogs’ keen noses lead the way, and when they unearth a truffle, the excitement is palpable. Children will especially love watching the Lagotto Romagnolo dogs, known for their exceptional truffle-hunting abilities, as they sniff out valuable truffles beneath the forest floor. It’s a great way for kids to get out into nature and experience the thrill of discovery firsthand.

After the hunt, savor a meal featuring freshly shaved truffles, transforming simple dishes like pasta or risotto into gourmet delicacies.

Our newest villa, Le Macie, is perfectly situated near private truffle reserves, offering you an exclusive opportunity to join guided tours led by expert truffle hunters.

Tip: For the ultimate truffle experience, don’t miss the San Giovanni d’Asso Truffle Festival, where the entire town celebrates these subterranean treasures with tastings, cooking demonstrations, and a bustling truffle market.

4. “Chestnuts roasting on an open fire…”

I bet you can’t say that without singing it!

In Tuscany, the humble chestnut, known as castagne (Cast-AH-nyeh), takes center stage during the Festa di San Martino, held on November 11. As the air turns crisp, the sweet scent of roasting chestnuts fills the streets of Tuscan villages. This signals the end of the agricultural year and the beginning of winter preparations.

Families gather around open fires to roast castagne and enjoy their warm, nutty flavor. Chestnuts are not only eaten on their own but also used in a variety of dishes. They appear in everything from soups and stews to desserts like castagnaccio (chestnut cake).

The Mugello region is particularly famous for its chestnuts. They have earned Protected Geographic Indication status for their exceptional quality.

Tip: The Sagra delle Castagne in Marradi is a chestnut festival you can’t miss! Located north of Florence in the Mugello region, this rural town is famous for Marroni di Marradi, one of the world’s most highly regarded chestnut types. During the festival, the streets are packed with visitors, musicians, and food booths. Of course, chestnuts roast in antique iron roasters over open fires. Children play freely, while bands or local musicians entertain. The people of the town come out to enjoy the afternoon or evening.

Old Traditions New Memories

Traditions are amazing—they are the glue that bonds friends and family together, which is why they exist all over the world. Here in Tuscany, we warmly welcome our clients to experience some of our time-honored traditions this fall. Some of these traditions date back to the Etruscans, carrying centuries of history and connection to the land.

Perhaps this is the year to try something different and new. Whether it’s pressing your own olive oil, picking grapes for your own Chianti, truffle hunting with adorable Lagotto Romagnolo dogs, or roasting chestnuts with locals in a piazza, Tuscany in the fall offers a unique opportunity to embrace new traditions for you and your family.

At Tuscan Dream, we are here to help you personalize your itinerary, travel plans, and pick the perfect villa for your stay.

Let us guide you through Tuscany’s rich culture and traditions, creating a Thanksgiving or holiday experience filled with warmth, family, and memories.

Book your stay in one of our luxurious villas now! We will help you plan the rest.