Planning a day in Siena that combines wine, food, and scenery? The Discover Chianti Classico Wines DiWine Experience offers a thoughtfully curated journey through one of Italy’s most celebrated wine regions. With a licensed sommelier as your guide, small-scale wineries, and a local lunch, this tour promises an authentic taste of Tuscany’s legendary wines and flavors.
We’re impressed by how this experience balances expert knowledge with a relaxed, personal vibe. Two things that especially stand out are the passion and professionalism of Emanuele, your driver and guide, and the focus on boutique wineries that aren’t often on the tourist trail. The only potential drawback? The price point of around $290 per person might seem steep for some, but considering the personalized service, quality tastings, and delicious lunch, many will find it worthwhile. It’s best suited for wine lovers eager to learn, foodies, or anyone craving a genuine Tuscan experience away from the crowds.
Key Points

- Expert guidance: Led by a passionate, knowledgeable sommelier who shares wine and food secrets.
- Authentic visits: Small, boutique wineries reveal the true spirit of Chianti’s craftsmanship.
- Scenic vistas: Enjoy breathtaking views of the Tuscan countryside throughout the day.
- Gourmet lunch: Savor a typical Tuscan meal in an off-the-beaten-path location.
- All-inclusive: Price covers transportation, tastings, and lunch—no hidden costs.
- Small group size: Max 8 travelers ensures personalized attention and a relaxed atmosphere.
An In-Depth Look at the Tour Experience

You can also read our reviews of more tours and experiences in Siena.
Meeting Up and Transportation
Your day begins at the Basilica Cateriniana San Domenico in Siena at 9:30 am. The meeting point is conveniently near public transportation, making it accessible whether you’re staying in Siena or arriving from elsewhere. Once everyone is assembled, you’ll hop into a comfortable, air-conditioned vehicle—important, given Italy’s warm climate, especially in summer.
The transportation isn’t just about getting from point A to point B; it’s part of the experience. Emanuele, your guide, is also your driver, which means he’s free to focus on your comfort and safety while sharing his extensive knowledge along the way.
The Boutique Wineries
Unlike large, commercial wineries, the stops on this tour are small, family-run establishments. This is where the tour really shines. These wineries often don’t have the big marketing budgets but produce wines with genuine personality and care. You’ll taste classic Chianti Classico, and Emanuele is eager to explain what makes each producer special, from soil types to aging techniques.
Rosemarie_M’s review captures this well: she praises Emanuele as “a professional driver, professional drinker (not during the tour, of course!), and a fantastic tour guide… very knowledgeable, personable, funny, and passionate about his town and country.” His ability to blend expertise with friendliness creates a welcoming environment for learning and tasting.
The Lunch Break
After touring the wineries, you’ll enjoy a typical Tuscan lunch in a charming, off-the-beaten-path setting. The meal is designed to complement the wines you’ve sampled—expect local cheeses, cured meats, fresh bread, and seasonal dishes. This isn’t just a meal; it’s a chance to experience genuine Tuscan hospitality and flavors, often a highlight for past guests.
Tasting and Learning
Throughout the day, Emanuele will guide you through wine tastings, explaining nuances like aroma profiles, aging processes, and what to look for when tasting wine. His passion is contagious, and he’s happy to answer questions, making this a fantastic experience for both newcomers and seasoned wine lovers.
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Scenic Views and Authentic Atmosphere
The views throughout the tour are spectacular—rolling hills, vineyards stretching to the horizon, quaint farmhouses—every turn offers a perfect photo opportunity. This scenery not only enriches the tasting experience but also makes the day memorable.
Who Will Love This Tour?
This experience is perfect for those who want to expand their wine knowledge without feeling overwhelmed. It’s also ideal for travelers craving a personalized, authentic experience rather than a generic tour. If you appreciate good food, stunning landscapes, and engaging storytelling, this tour will resonate.
The Value of the Experience

At nearly $300 per person, this tour might seem pricier than some group outings, but it’s justified by the small group size, personalized guidance, quality tastings, and included lunch. The all-inclusive nature means you won’t have to worry about extra costs, which helps keep the experience relaxed and enjoyable.
What sets this apart from larger, more commercial wine tours is the intimate setting. Only up to 8 travelers ensure ample opportunity for questions, conversation, and a feeling of genuine discovery. The tour’s focus on boutique wineries also means you’re supporting smaller producers, which many travelers find meaningful.
Authenticity and Education
Guests consistently praise Emanuele’s deep knowledge and personable manner. One reviewer highlights his ability to make the day both fun and educational, adding a layer of enjoyment that goes beyond simple tastings. The opportunity to learn about the secrets of Tuscan winemaking from a licensed sommelier enriches the experience considerably.
Practical Considerations
The 8-hour duration balances a comprehensive experience with manageable pacing. The schedule allows enough time at each stop for tasting, conversation, and photos, without feeling rushed. Remember, the minimum age for alcohol consumption is 18, making it suitable for adult travelers. The tour is available as a private option if you prefer exclusivity, or as a group experience, which can be more budget-friendly.
Final Thoughts
The Discover Chianti Classico Wines DiWine Experience offers an authentic, intimate glimpse into Tuscany’s celebrated wine culture. Led by a passionate, knowledgeable guide, you’ll visit charming boutique wineries, learn about traditional winemaking techniques, and enjoy a delicious local meal—all in a setting of breathtaking scenery.
This tour provides excellent value for those who prioritize quality over quantity. It’s particularly well-suited for wine enthusiasts eager to deepen their understanding and those who appreciate a personal touch in their travel experiences.
While the price is on the higher side, the small-group atmosphere, private transportation, and expert guidance make it a memorable investment in your Tuscan journey. Whether you’re celebrating a special occasion or simply want to indulge in authentic flavors, this tour delivers a genuine taste of Chianti’s best.
Frequently Asked Questions

Is the tour suitable for wine beginners?
Absolutely. Emanuele is great at explaining things clearly and sharing his passion, making it accessible whether you’re new to wine or a seasoned aficionado.
Does the tour include transportation?
Yes, you’ll be transported in a comfortable, air-conditioned vehicle throughout the day, with pickup and drop-off at the designated Siena meeting point.
How long is the tour?
The entire experience lasts about 8 hours, allowing ample time for visiting wineries, tasting, eating, and enjoying the scenery.
Are meals included?
Yes, a typical Tuscan lunch is included in the price, served at an off-the-beaten-path location, adding to the authentic local experience.
Can the tour be private?
Yes, private tours are available upon request, providing a more exclusive experience tailored to your group.
What is the maximum group size?
The tour is limited to 8 travelers, ensuring a personal, engaging atmosphere.
What wines will I taste?
You will sample Chianti Classico wines, with tastings guided by Emanuele to highlight what makes each one special.
Is this tour good for photography?
Definitely. The scenic vineyard views, rolling hills, and charming countryside make for perfect photo opportunities throughout the day.
This Discover Chianti Classico Wines DiWine Experience offers a well-rounded, authentic peek into Tuscany’s wine and food culture, with the intimacy of small-group touring and expert guidance. It’s a memorable way to deepen your appreciation for Italy’s most famous wine region—an experience worth considering on your Tuscan itinerary.
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