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Explore Tuscany’s Chianti Classico with a knowledgeable sommelier guide, visiting boutique wineries, tasting top wines, and enjoying authentic Tuscan cuisine.
Discover the Charm of Chianti Classico Wines with a Personal Touch
This tour offers a well-rounded taste of Tuscany’s famous Chianti Classico region, led by Emanuele, a licensed sommelier and driver who combines his deep knowledge with a friendly, personable approach. With visits to small boutique wineries, a traditional Tuscan lunch, and stunning vistas, it promises an authentic experience that emphasizes quality over quantity.
What we really love about this experience is how it balances expert guidance with a relaxed, intimate atmosphere—making wine tasting accessible for all levels of wine enthusiasts. A possible downside could be the cost—$290.53 per person—though many find the personalized approach and exclusive visits justify the price. This tour suits travelers looking for a deep dive into Tuscan wines paired with genuine local foods, especially if they appreciate a more intimate, small-group setting.


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Your adventure kicks off at the Basilica Cateriniana San Domenico in Siena at 9:30 am. The meeting spot is convenient, close to public transportation options, making it easy to access from central Siena. The tour lasts about 8 hours, a good amount of time to savor wines, learn about production, and enjoy a relaxed lunch without feeling rushed.
The transportation is a private, air-conditioned vehicle, ensuring a comfortable ride through Tuscany’s rolling hills. The small group size—no more than 8 people—means you’ll get plenty of attention from Emanuele, whose role as both guide and driver adds a layer of professionalism and safety.
Meet Emanuele, the Sommelier Guide
Emanuele is more than just a driver; he’s a licensed sommelier with a contagious passion for Tuscan wines and culture. As a reviewer noted, he’s “very knowledgeable, personable, funny, and his passion for his country/town was enjoyable to read.” His expertise means you’ll learn not just about what you’re tasting but also about the history and secrets behind the wines.
Boutique Winery Visits
You’ll visit carefully selected, small, boutique wineries that are off the beaten path. These family-run operations offer a glimpse into authentic Tuscan winemaking, away from commercialized tours. Expect to taste a variety of Chianti Classico wines, where the focus is on quality and unique regional expressions.
Wine Tasting
The tasting sessions are guided by Emanuele, who will explain the nuances of each wine. Guests have praised his ability to make the complex aspects of wine accessible, regardless of prior knowledge. From reviews like “a fantastic tour guide,” it’s clear that his passion helps guests appreciate the subtle differences that make each wine special.
Tuscan Lunch in a Hidden Gem
Lunch is served in a quiet, scenic setting, away from travelers’ eyes. You’ll indulge in traditional Tuscan fare—local cheeses, cured meats, bread, and regional specialties—paired with regional wines. One reviewer appreciated the “off the beaten path” lunch spot, which adds to the genuine local vibe.
Enjoying the Views
Throughout the day, you’ll take in sweeping vistas of Tuscany’s rolling hills, vineyards, and olive groves. These moments of scenic beauty are a highlight, providing perfect photo opportunities and a chance to soak in the region’s authentic landscape.
Knowledgeable Guide
Emanuele’s role as both sommelier and driver is a real asset. His insights turn the tasting into an educational experience, making it suitable whether you’re a novice or a seasoned wine lover. As one reviewer said, “his passion for his country/town was enjoyable to read,” which translates into a more engaging experience.
Authentic and Small-Scale
Visiting small wineries means you’re likely to taste wines that are not commercially available in stores, giving you a true sense of the region’s diversity. The limited group size ensures you won’t be lost in a crowd, and you’ll receive tailored attention.
Quality of Food and Wine
Guests consistently praise the quality of the wines and the authenticity of the food. The focus is on regional products, which enhances the overall experience of a genuine Tuscan culinary and winemaking journey.
Value for the Price
While at nearly $290 per person, the tour isn’t the cheapest option, the inclusion of private transportation, expert guidance, tastings, and a full lunch makes it a good value for those seeking depth and authenticity.

This experience is ideal for wine enthusiasts eager to learn more about Chianti Classico, especially those who appreciate small-scale, authentic wine producers. It’s also perfect for travelers who want a personalized, intimate tour rather than large group excursions. Food lovers will enjoy the regional lunch, and anyone interested in Tuscan landscapes will be captivated by the views.
Couples, small groups of friends, or solo travelers seeking a meaningful taste of Tuscany will find this tour offers both education and enjoyment. If you’re after a relaxed but informative day with expert guidance, this experience will meet and exceed your expectations.
This Chianti Classico Wines DiWine Experience offers a thoughtfully curated journey into Tuscany’s most famous wine region. Led by Emanuele, a passionate licensed sommelier, guests gain insight into the winemaking process, taste exceptional boutique wines, and enjoy a delicious Tuscan lunch in a scenic, off-the-beaten-path location. The small-group format ensures a personalized experience, making it perfect for those who want to avoid tourist crowds and connect more deeply with local producers.
While the price might seem high at first glance, the quality of visits, expert guidance, and authentic regional cuisine justify it for serious wine lovers or those looking for a memorable, educational day in Tuscany. Whether you’re a novice or a connoisseur, this tour promises to deepen your appreciation of Chianti’s unique flavors and scenery.
If authentic Tuscan wine, intimate winery visits, and expert storytelling appeal to you, this experience is a strong choice. It combines education, scenic beauty, and genuine local flavor into a day that’s both enjoyable and enriching.

What is included in the tour?
The tour includes private transportation in an air-conditioned vehicle, visits to boutique wineries with tastings, a traditional Tuscan lunch, and the guidance of a licensed sommelier.
How long does the tour last?
It lasts approximately 8 hours, starting at 9:30 am and ending back at the meeting point.
Where does the tour start and end?
It begins at Basilica Cateriniana San Domenico in Siena and finishes back at the same location.
Can the tour be booked privately?
Yes, private options are available upon request, providing a more personalized experience.
What is the group size?
The maximum group size is 8 travelers, ensuring an intimate atmosphere.
Is this suitable for all ages?
The tour is designed for guests aged 18 and over due to alcohol tasting.
Are vegetarian or special dietary requests accommodated?
While not explicitly stated, the focus on regional cuisine suggests flexibility; it’s best to inquire directly with the provider.
How do I confirm my booking?
Booking confirmation is received within 48 hours, subject to availability. You’ll receive details on how to proceed after booking.
In essence, the Discover Chianti Classico Wines DiWine Experience offers a genuine, well-rounded taste of Tuscany’s wine and food culture, led by a knowledgeable guide in an intimate setting. It’s a perfect pick for travelers wanting to deepen their understanding of Chianti wines while savoring regional flavors amidst stunning scenery.