Autumn in Tuscany is an invitation to slow down, breathe and savor. The hills are tinged with gold and copper, the scents of the earth become more intense, and every village seems to tell a story. In this unique context, the “San Gimignano Wine Tasting with Truffle Tour” fits in: a journey into the heart of Tuscan excellence, between glasses of Vernaccia and the mysterious call of truffles.
San Gimignano: A Medieval Pearl World Heritage Site
San Gimignano, known as the “Manhattan of the Middle Ages” for its tall towers, stands among the Sienese hills like a timeless jewel. This village, a UNESCO heritage site, is famous not only for its intact architecture but also for the production of Vernaccia di San Gimignano, one of the first Italian wines to be awarded DOC status back in 1966.
Walking through its cobblestone streets, one is immersed in an atmosphere of yesteryear. And this is where the experience starts: a day designed to celebrate the perfect combination of wine and truffles, symbols of the Tuscan gastronomic tradition.
Part 1: Tasting Vernaccia Wines at the Winery
The tour begins at a family-run winery nestled among the vineyards of San Gimignano. Welcoming visitors are the producers themselves, ready to tell the story of their wine and their land.
What is tasted:
- Vernaccia di San Gimignano DOCG: dry, mineral, with floral and citrus scents.
- Rosso Toscano IGT: often from Sangiovese vines, full-bodied and persistent.
- Vin Santo with cantucci: sweet, perfect to end the tasting.
Each tasting is accompanied by typical local products: cured meats, aged pecorino, extra virgin olive oil and Tuscan crostini. But it’s not just about tasting: it’s an opportunity to learn. Sommeliers explain the wine’s characteristics, the winemaking process, and how Vernaccia reflects the area’s unique terroir.

Part 2: Truffle Hunting in the Tuscan Woods.
With the tasting over, it is time to venture into the woods. In the company of an experienced truffle hunter and his faithful trained dogs, the truffle hunt begins. A fascinating activity that blends nature, patience and intuition.
What it turns out to be:
- Truffle varieties found in autumn (such as white truffle and black hooked truffle).
- How dogs are trained to sniff out the valuable underground mushroom.
- The differences between professional and amateur collecting.
As you walk through the trails, you learn to recognize symbiotic trees (oak, poplar, hazel) and understand the importance of sustainability in harvesting. The activity is also suitable for those who have never participated in a truffle hunt: it is engaging, educational and deeply connected to the area.
Part 3: Truffle Gourmet Lunch.
After picking truffles, you reach a typical Tuscan trattoria or agritourism estate for a gourmet lunch. Here, the chef uses the freshly found truffles to prepare simple but intensely aromatic dishes.
Typical menu:
- Croutons with butter and truffle
- Handmade noodles with fresh truffles
- Fried eggs with truffle shavings
- Traditional Tuscan Sweets
- Wine pairing (Vernaccia, Chianti or Tuscan Red)
Each course is a celebration of authentic Tuscan flavor. The truffle, freshly grated, releases all its aroma in dishes that enhance the raw material.

Why This Tour is So Special
- Authentic seasonality: the fall season is the ideal time for truffles and new wines.
- Complete experience: wine, nature, culture and gastronomy in one day.
- Experienced local guide: each tour stop is accompanied by local professionals.
- Small groups: intimate experience, without the mass tourism.
- Scenic context: the Chianti hills and the skyline of San Gimignano in the background.
Technical and Logistical Information
- Duration: about 6 hours
- Recommended season: September, October, November
- Number of participants: maximum 8 people per group
- Included: transportation by private NCC, guide, wine tasting, truffle hunting, lunch
- Languages available: Italian, English, on request also French or German
- Departure point: Florence or San Gimignano, with the possibility of personalized pickup
Tips for Participants
- Wear comfortable shoes suitable for walking in the woods
- Bring a light jacket or raincoat: Tuscan weather in autumn can vary
- No prior knowledge needed: the activity is designed for everyone
- Recommended camera: the views are breathtaking
A Perfect Gift or Experience to Remember
This tour is also a wonderful gift idea for anniversaries, birthdays or couples experiences. Customized gift vouchers, valid for the entire fall season, can be purchased.
Conclusion
The “San Gimignano Wine Tasting with Truffle Tour” is more than just an excursion: it is a sensory journey into the true soul of Tuscany.
An experience that combines enological excellence with the culture of the land, at a time of year when nature gives its most intense and authentic flavors.
If you want to experience this adventure or give it as a gift to someone you love, contact Tuscany By GC – NCC Florence to arrange your personalized tour.
Tuscany is waiting for you, scented with truffles and filled with good wine.