Montalcino: Vertical Tasting

Montalcino: Vertical Tasting – A Genuine Taste of Tuscany’s Winemaking Heritage

Traveling through Tuscany, especially around Montalcino, is a treat for wine lovers and curious explorers alike. This vertical tasting experience at Villa le Prata promises a chance to appreciate the land’s historic connection to winemaking, all within the comfort of a beautifully preserved 19th-century villa. While I haven’t done this tour myself, the details make it clear that it could be a memorable outing for those who appreciate authentic wine stories and scenic vineyards.

What we really like about this experience is the intimate setting—limited to just four participants—and the chance to sample three vintages of Brunello alongside natural wine and extra virgin olive oil. The setting, a historic villa once used by counts and bishops, adds a layer of charm that feels both exclusive and welcoming. A potential downside? The tour is quite short—about a day—and doesn’t include transportation, so you’ll need to plan your logistics carefully. That said, if you’re a wine enthusiast eager to learn about Brunello or enjoy a calm, small-group experience, this tour could hit just the right note.

This experience is especially suited to travelers who want a hands-on, educational glimpse into Tuscany’s winemaking traditions without the crowds or overly commercial vibe. It’s also perfect if you’re interested in exploring historic Italian villas or simply want a peaceful day among vineyards with expert guidance.

You can check availability for your dates here:

Key Points

• Exclusive small group: Limited to 4 participants, ensuring a personal experience.
• Historic setting: A 19th-century villa with a storied past, now hosting wine tastings.
• Diverse tastings: Includes three different vintages of Brunello, natural wine, and EVO oil.
• Educational focus: Led by a professional sommelier, providing insights into the wines and land.
• Beautiful surroundings: Walking through cypress-lined avenues and vineyards.
• Price and duration: At $65 per person for a one-day experience, it offers a good value for those passionate about wine.

A Closer Look at the Montalcino Vertical Tasting

When considering a wine tour in Tuscany, the appeal often hinges on the setting and the stories behind each sip. This experience at Villa le Prata really capitalizes on both. The villa itself paints a picture of old-world elegance, originally built as a hunting lodge, then a summer residence for bishops, before becoming a winery run by the Losappio family since 1980. That history isn’t just window dressing—it’s woven into the fabric of the visit.

As we understand, the tour begins with a walk along a cypress-lined avenue, a classic Tuscan scene that immediately transports you from everyday life to a picture-perfect landscape. The vineyard walk is an opportunity to listen to the history of the villa and the land, which adds depth to the tasting experience. You might find yourself appreciating the nuances of the land more, knowing the historical significance and the careful cultivation that goes into each vine.

Once inside the Cantinetta delle Annate, the real highlight begins. Here, the sommelier guides you through tasting three vintages of Brunello, giving you a chance to compare how the wine develops over different years. The inclusion of natural wine and extra virgin olive oil broadens the experience a bit beyond just classic Brunello, offering a fuller sense of the region’s culinary culture.

The price of $65 seems reasonable when you consider that you’re getting a private, small-group experience with expert commentary. The tour’s length is ideal for a relaxed afternoon, especially if you’re already exploring Tuscany. Keep in mind, the tour doesn’t include transportation, so you’ll need your own way to get there—Villa le Prata is the meeting point.

Feedback from past reviews has been positive, mainly praising the warmth of the host, the intimate setting, and the quality of the wines. One reviewer shared, “It was a special, intimate experience—like visiting a friend’s house where they just happen to be a talented winemaker.” Another appreciated the diversity in the tasting, noting that “it really helped me understand how Brunello changes over the years.”

The experience isn’t suitable for children under 9, which makes sense given the focus on wine and the nature of the tasting. It’s primarily designed for adults who want a calm, informative, and deliberately small experience.

What to Expect and Practical Tips

The tour lasts roughly a day, with the core activity being the visit to the historic villa, the vineyard walk, and the tasting session itself. You’ll start with a gentle stroll through the vineyards, hearing about the land’s past and how it influences the wines. This isn’t a walk-and-sip event; it’s a story-rich experience where knowledge and appreciation deepen with each vintage.

Inside, the tasting is held in an elegant room that’s cozy yet refined. Expect to taste the three vintages side-by-side, observing how they differ in aroma, color, and flavor. The addition of extra virgin olive oil offers a taste of regional production, pairing nicely with bread or cheeses if you’re curious to explore more.

Since the tour is limited to four participants, you’ll get personalized attention and a chance to ask many questions. The professional sommelier will explain the nuances of each vintage, the natural wine process, and the land’s influence. For real wine enthusiasts, this is a chance to deepen your understanding of Tuscany’s winemaking methods.

The Value for Money

At $65 per person, this experience strikes me as a good value. You’re paying for a private, guided tasting at a historic villa—not just a tasting in a commercial cellar. Considering that most tastings in Tuscany can easily cost more, especially if they include multiple vintages and a guided explanation, this one seems fairly priced. The focus on natural wine and olive oil also adds a distinctive touch that separates it from more generic tours.

Keep in mind that transportation isn’t included, so plan accordingly. If you’re staying nearby, it’s a simple matter of driving or arranging a ride; if not, you might want to coordinate with your accommodation or explore other transport options.

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Who Will Appreciate This Tour?

This experience is ideal for adults who love wine and want a quiet, personal encounter with Tuscany’s winemaking tradition. It’s especially good if you’re curious about Brunello and its evolution through different vintages. History buffs will enjoy the historic setting, and those interested in natural wines will find the inclusion of that category refreshing.

Since it’s a small-group tour, it offers a more intimate, less commercialized atmosphere—great for those who prefer quality over quantity. It’s not suited for children under 9, so keep that in mind if you’re traveling with family.

If you’re after a relaxed, educational, and scenic experience that emphasizes quality and authentic storytelling, this tour has a lot to offer.

Frequently Asked Questions

Is transportation included in this tour?
No, transportation isn’t included, so you will need to arrange your own way to Villa le Prata. The meeting point is set, and you should plan your travel accordingly.

How long is the tour?
The experience lasts about one day, focusing on the vineyard walk, villa visit, and tasting session.

Is the tour suitable for children?
It’s not suitable for children under 9 years old, primarily because of the wine tasting and adult-focused environment.

Does the tour include multiple types of wines?
Yes, you will taste three different vintages of Brunello, along with natural wine and EVO oil.

What language is the tour conducted in?
The tour is available in both English and Italian.

How many people are in each group?
The group is limited to just 4 participants, ensuring a personalized experience.

Can I cancel the tour?
Yes, you can cancel up to 24 hours in advance for a full refund.

Is the experience worth the price?
Given the small-group setting, historic ambiance, variety of tastings, and expert guidance, it offers good value for wine lovers wanting an authentic taste of Tuscany.

Final Thoughts

If you’re looking for a relaxed, intimate, and genuinely educational experience in Tuscany, this Montalcino vertical tasting at Villa le Prata is a solid choice. You’ll enjoy a beautiful setting, learn from a knowledgeable guide, and get to taste some of the region’s finest wines—without the crowds or commercial fuss. It’s especially suited for travelers who crave authenticity, quality, and a taste of history.

While it’s not a tour for families with young children or those simply seeking a quick wine fix, it offers a deeper connection to Tuscany’s winemaking legacy. The price is reasonable for what’s included, and the small group ensures personal attention, making it a memorable part of any Tuscan adventure.

Whether you’re a seasoned wine enthusiast or just want to understand what makes Brunello special, this experience will leave you with both knowledge and lovely memories of Italy’s most famous wine country.

You can check availability for your dates here: