A Taste of Bolgheri: A Private Wine Tour with a Top Sommelier
Imagine spending a day in the rolling hills of Tuscany, but with a focus on one of Italy’s most celebrated wine regions—Bolgheri. This private tour, guided by Simone Vergamini—who was crowned “Best Sommelier of Tuscany 2023”—offers a focused, intimate experience of two famous wineries, complete with cellar visits, tastings, and local snacks. It’s more than just wine tasting; it’s a chance to learn about the area’s unique traditions, vineyards, and the craftsmanship behind every bottle.
What I particularly like about this experience is Simone’s genuine enthusiasm and deep knowledge. He not only guides you through the vineyards and cellars but also shares stories that add a sense of place—making the wines come alive in a way you can’t get from a generic tasting. Plus, the visit to Bolgheri itself is delightful, with its picture-perfect streets and charming atmosphere.
One consideration to keep in mind is that while the tour is quite comprehensive, it’s designed for those who truly want an insider’s look at Bolgheri’s viniculture—so it might not be ideal if you prefer a more relaxed, less structured day. Also, the 8 to 9-hour duration means you’ll want to be comfortable with a full-day outing.
Key points / Takeaways
- Expertly Guided: Simone Vergamini’s reputation as Tuscany’s top sommelier ensures a knowledgeable, engaging host.
- Authentic Visits: The tour visits two acclaimed wineries—usually Chiappini and Grattamacco—highlighting the best of Bolgheri’s wine scene.
- Educational & Entertaining: Expect stories about local traditions, vineyard details, and wine-making nuances, making it educational for enthusiasts and curious travelers alike.
- Tastings & Local Flavors: Beyond wine, enjoy tasting regional products like olive oil, cheese, and salami, paired with your wines.
- Picture-Perfect Village: The stop in Bolgheri offers a lovely lunch in a top wine shop—perfect for soaking in the village’s charm.
- Personalized Experience: As a private tour, only your group participates, which allows for tailored questions and a more relaxed pace.
Entering the Heart of Bolgheri’s Vineyards and Cellars

The day begins early, with pickup in a comfortable, air-conditioned vehicle. Having a private guide like Simone offers the flexibility to focus on what interests you most—be it the vineyard practices or specific wines. The first stop is Chiappini Winery, where you’ll stroll through vineyards and see the cellar up close. The tasting here usually lasts around an hour and a half, giving you ample opportunity to understand the wine production process and sample some of the finest Bolgheri reds and whites.
Simone’s reviews highlight his graciousness and passion. One reviewer mentioned, “Simone was a gracious host/guide. He brought us to 2 amazing wineries and reserved a wonderful restaurant for lunch.” You’ll be immersed in the sights, sounds, and smells of working wineries—an experience that elevates tasting from a simple sip to a story of land and craft.
The second winery, Tenuta Podere Grattamacco (or occasionally Tenuta di Vaira or Le Novelire), offers a similar behind-the-scenes look and tastings. Expect to touch the vines, walk through historic cellars, and sample wines that represent the pinnacle of Bolgheri’s style, renowned for its Bordeaux-inspired blends.
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The Charm of Bolgheri Village and Local Lunch

After winery visits, the tour pauses in Bolgheri proper—one of Italy’s most picturesque villages. Here, you’ll enjoy a two-hour stop for lunch, usually at the Tognoni wine shop, which is highly praised for its quality and ambiance. This is a relaxed time to sample local delicacies—think bread, cheese, salami, and local olive oil—paired with superb wines.
Many reviewers comment on how the lunch complements the wine experience: “Lunch in Bolgheri was top quality,” and “the restaurant Simone reserved was wonderful.” The village itself is a delight, with cobblestone streets, colorful houses, and panoramic views that make it feel like stepping into an Italian postcard.
The Value of a Private, Guided Experience

At $347.05 per person, this tour might seem steep at first glance, but it’s a thoughtful investment in a comprehensive, curated experience. The private format ensures your group’s comfort and flexibility—no crowded buses or rushed schedules—and the in-depth knowledge of Simone enhances your understanding of both wines and local customs.
The tour includes transportation in a climate-controlled vehicle, tastings at both wineries, snacks, bottled water, and the chance to ask as many questions as you like. You also get the added bonus of a knowledgeable guide who loves sharing his passion and insights—something you might miss on a self-guided visit.
While lunch isn’t included in the price, Simone’s recommendation of a highly-rated wine shop and restaurant makes dining arrangements simple and convenient. You can also choose your preferred spot for lunch if you have a favorite.
Who This Tour Is Perfect For

This experience suits wine lovers eager to learn directly from an expert, as well as those who appreciate authentic Italian village atmospheres. It’s ideal for travelers who want a structured, informative day without sacrificing intimacy or personal attention. If you’re after a relaxed, yet educational exploration of Bolgheri’s best wineries, this tour hits the mark.
It also appeals to visitors with a keen interest in Italy’s wine culture, as Simone’s engaging storytelling and visits to renowned wineries deepen your appreciation for the region’s viniculture.
Price and Logistics: Balancing Cost and Experience

At roughly $347 per person, this tour offers significant value if you enjoy personalized attention and in-depth winery visits. The full-day schedule ensures you see the best of Bolgheri in a relaxed, unhurried manner—something hard to replicate on your own. The included stops, tastings, and snacks are thoughtfully curated to give you a well-rounded taste of the region.
The tour’s booking window—usually 99 days in advance—indicates it’s a popular choice among dedicated wine travelers. It starts early at 9:30 am, giving you plenty of daylight hours for exploration and relaxation.
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Final Thoughts

This private wine tour with Simone Vergamini is a standout choice for anyone seeking a meaningful, authentic experience in Bolgheri. From his extensive knowledge and approachable manner to the carefully chosen wineries and charming village stop, it offers a balanced mix of education, indulgence, and local charm.
The highlight for many is the chance to taste exceptional wines in a scenic setting, guided by someone who truly loves sharing his expertise. The option to pair tastings with regional snacks and enjoy Bolgheri’s picturesque streets makes for a memorable day.
While it costs a bit more than a generic wine tasting, the value lies in the quality of the experience—personal, insightful, and beautifully curated. Whether you’re a seasoned wine enthusiast or simply looking to enjoy a slice of Italy’s renowned viticulture, this tour delivers an enjoyable, enriching adventure.
FAQ

How far in advance should I book this tour?
It’s best to book about 99 days in advance to secure your spot, especially during peak season.
What is included in the price?
The tour covers transportation, visits and tastings at two wineries, bottled water, snacks like olive oil, bread, cheese, and salami.
Is lunch included?
No, lunch isn’t included in the price, but Simone recommends a top wine shop and restaurant in Bolgheri for a memorable meal.
What is the duration of the tour?
The entire experience lasts about 8 to 9 hours, starting at 9:30 am.
Can I customize the experience?
Since it’s a private tour, you can ask questions and enjoy a tailored visit, but the itinerary follows the standard visits to two wineries and the village stop.
Is this tour suitable for all ages?
Most travelers can participate, and service animals are allowed, but it’s best for those comfortable with a full-day outdoors and walking.
What happens in case of bad weather?
The experience requires good weather. If canceled due to rain or poor conditions, you’ll be offered a different date or a full refund.
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