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Discover Chianti Classico wines with a knowledgeable sommelier in Siena. Enjoy visits to boutique wineries, authentic Tuscan food, and stunning views in this 8-hour tour.
The Discover Chianti Classico Wines DiWine Experience offers a full day of exploring some of Tuscany’s most celebrated wines and local flavors, all for $290.53 per person. Departing from Siena, this 8-hour guided tour is perfect for anyone eager to learn about Chianti Classico wines with a passionate expert by your side. Led by Emanuele, a licensed sommelier, the tour combines visits to small boutique wineries with a typical Tuscan lunch in a charming, off-the-beaten-path location.
This tour stands out not just for its intimate group size—capped at 8 travelers—but also for the personal attention and deep knowledge shared by Emanuele. While most bookings are in group settings, private options are available on request, providing flexibility for different types of wine enthusiasts. The tour’s emphasis on authentic wines, scenic views, and local cuisine makes it a comprehensive experience for those wanting to truly understand the essence of Chianti.


The tour begins at the Basilica Cateriniana San Domenico in Siena, a central location easily accessible via public transportation. From this meeting point, Emanuele—a knowledgeable driver and guide—takes you on a scenic journey through the heart of Chianti’s vineyards. The route emphasizes comfort and convenience, with air-conditioned private transportation ensuring a relaxed day from start to finish.
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One of the tour’s highlights is the chance to visit small boutique wineries rather than large commercial estates. These intimate stops allow for a more personalized wine-tasting experience, where Emanuele shares insights into the winemaking process and the unique qualities of each winery’s products. The focus on boutique wineries means access to exclusive tastings that aren’t available elsewhere, making this an ideal choice for wine connoisseurs or those curious to discover authentic Chianti Classico.

Throughout the day, you will sample a selection of Chianti Classico wines, renowned for their quality and distinctive character. Emanuele’s expertise ensures you gain a deeper understanding of the different varietals, their aromas, and what makes each wine special. The tastings are complemented by an appreciation of the winemaking techniques used in Tuscany, even if you have little prior knowledge.

Lunch is a key part of this experience, served in a typical Tuscan setting away from tourist crowds. The location offers picturesque views that showcase the region’s rolling hills and vineyards. The meal features local Tuscan products, providing a genuine taste of the area’s culinary traditions. This scenic meal break enriches the overall experience, making the day both flavorful and visually stunning.

One of the aspects most appreciated in reviews and descriptions is the breathtaking scenery encountered throughout the tour. Visitors enjoy spectacular vistas of vineyards, olive groves, and rolling hills that are characteristic of the Chianti region. These views are accessible during the drive and at various stops, enhancing the overall experience.

Emanuele, a licensed sommelier, leads the tour with warmth, humor, and an evident passion for Tuscan wines and culture. His storytelling style makes complex winemaking concepts easy to understand, creating a friendly environment for learning. The small group size ensures you receive personal attention, making it easier to ask questions and dive deeper into topics of interest.

The tour departs at 9:30 am from Basilica Cateriniana San Domenico in Siena. The tour concludes back at the same location, making it convenient for participants. Included in the price are private transportation, air-conditioning, lunch, and wine tastings. Confirmation is provided within 48 hours, and most travelers can participate, provided they meet the minimum age of 18.

Unlike larger, more impersonal wine tours, this experience emphasizes small group intimacy, allowing for a more relaxed and engaging day. The focus on boutique wineries and authentic Tuscan cuisine means travelers receive a genuine and memorable taste of Chianti. The knowledgeable guide, Emanuele, elevates the experience by sharing his passion and insights, making the day both educational and enjoyable.
While the tour offers a comprehensive wine and food experience, it is a full-day commitment of approximately 8 hours. Participants should be prepared for a day on their feet and comfortable walking or sitting during tastings and meals. The tour is non-refundable and cannot be changed once booked, so it’s best suited for those certain of their plans.
This tour provides an excellent value for those interested in Chianti wines, local cuisine, and scenic landscapes. The expert guidance of Emanuele and visits to small boutique wineries create an authentic and personalized experience. It’s especially well-suited for individuals or small groups who appreciate wine education combined with Tuscan charm.
While the full-day schedule requires some commitment, the combination of delicious food, exclusive tastings, and breathtaking views makes it a rewarding choice. This tour offers a deep dive into Chianti’s wine culture while allowing plenty of opportunities to relax, learn, and enjoy the beauty of Tuscany.
“Professional driver, professional drinker (not during the tour, of course!), and a fantastic tour guide.. that's Ema for you. A licensed sommelier…”
What is included in the tour price?
The price covers private transportation, air-conditioned vehicle, lunch, and wine tastings at boutique wineries.
Where does the tour start and end?
The tour departs and returns to Basilica Cateriniana San Domenico in Siena.
How long does the tour last?
The tour lasts approximately 8 hours, starting at 9:30 am.
Is this tour suitable for all ages?
Most travelers can participate, but alcohol consumption is restricted to those 18 years and older.
Can I book a private version of this tour?
Yes, private tours are available upon request, offering more personalized attention.
Is there a specific dress code?
While not explicitly stated, comfortable clothing suitable for walking and sitting during the day is recommended.
What should I bring?
It’s advisable to bring a camera, sunglasses, and any personal items needed for a day out.
What makes this tour different from other wine tours in Tuscany?
Its focus on small boutique wineries, authentic Tuscan cuisine, and the personalized guidance of a licensed sommelier set it apart.
Are there any physical requirements?
The tour involves some walking and outdoor viewing, but no strenuous activity is expected.
How do I confirm my booking?
Confirmation is received within 48 hours of booking, subject to availability.