VIP Chianti, Brunello wine & Pienza with lunch From Siena

This experience made our article of Our 15 Favorite Siena Lunch Experiences.

An Authentic Day in Tuscany: Exploring Chianti, Brunello, and Pienza

This VIP tour from Siena offers a full day immersed in the best of Tuscany’s countryside, history, and wine. For around $219 per person, you’ll spend roughly 8 to 9 hours visiting two boutique wineries, exploring two picturesque hilltop towns, and enjoying a delicious Tuscan lunch. Led by a knowledgeable guide, this small-group experience is designed for those who want intimacy, authentic tastes, and stunning scenery.

What we really appreciate about this tour is how it combines educational wine tastings with time to wander peacefully around charming towns. We also love the inclusion of a Medieval underground cave—a rare peek into history—and the fact that all transportation is arranged, removing the hassle of navigation or logistics. On the flip side, the tour’s pace might feel a little tight if you’re the type to linger, but for most travelers, it strikes a good balance.

Ideal for those who want a personalized experience without the crowds, this tour suits anyone curious about Tuscany’s wine scene, history buffs, or travelers eager to see iconic landscapes. If you value small-group intimacy and want to taste top-quality wines in boutique settings, this tour will likely meet your expectations.

Key Points

• Small-group size (max 6 people) ensures a personalized, relaxed experience.
• Includes visits to two boutique wineries with tastings of Brunello, Chianti, and Super Tuscans.
• Pienza exploration provides free time to wander this Renaissance jewel at your own pace.
• All transport is included, making logistics stress-free.
• A delicious Tuscan lunch with homemade pasta, Pecorino cheese, cold cuts, and bruschetta adds local flavor.
• Historical highlights include Siena’s underground Medieval cave and centuries-old winery cellars.

Exploring Siena and Its Hidden Depths

We start the day in Siena, a city famed for its medieval streets and vibrant history. Your guide will introduce you to Siena’s past, giving context to its significance as a hub of art and culture. Then, you’ll descend into a secret underground Medieval cave, dating back to 600 BC—an experience that adds a layer of mystery and authenticity. Based on reviews, visitors find these underground visits especially memorable, describing them as “a rare peek into history” and “absolutely fascinating.”

This segment sets the tone for a day that balances history, scenery, and tastes. Siena’s compact size makes it easy to explore, but this tour keeps you focused on highlights, leaving ample time for your own wandering at the end.

Chianti’s Organic Boutique Winery: A Taste of Authentic Tuscany

The first winery stop takes you to Castellina In Chianti, where a family-owned organic winery has been operating since 1904. You’ll walk through cellars dating back to 1500, witnessing traditional winemaking techniques that have been passed down through generations. The views over the Tuscan hills are breathtaking—rolling vineyards and cypress-lined roads that seem to go on forever.

Guests consistently praise the wine tastings as excellent, with Michelle noting that both wineries she visited “were amazing.” The experience is not just about sampling wine but learning about its production—how the grapes are grown, harvested, and turned into some of the world’s most celebrated wines.

The highlight here is the Tuscan lunch paired with wines—homemade pasta, Pecorino cheese, cold cuts, and bruschetta—offering a true taste of regional cuisine. The value of this experience is clear: you get both a tour of historic cellars and a hearty, authentic lunch, all in a setting with breathtaking views.

Discovering Brunello in Montalcino

Later, you’ll visit Montalcino, famous for its Brunello di Montalcino, which in 2024 was listed as the best wine in the world. Here, a family-owned boutique winery invites you to explore cellars and vineyards, where you’ll learn the secrets behind creating this coveted wine. The views over the valley from Montalcino are truly impressive, giving you a sense of the landscape that influences the wine’s character.

Multiple reviews praise the Brunello tasting as insightful and enjoyable. Alan G. shared that the guide “created a plan that worked perfectly,” indicating how flexible and accommodating the tour can be—allowing you to focus on what interests you most. The opportunity to taste exceptional wines in a relaxed, boutique setting makes this stop a highlight.

Pienza and the Val d’Orcia: A Renaissance Masterpiece

No trip to Tuscany is complete without a visit to Pienza, often called the “touchstone of Renaissance urbanism”. With its harmonious streets and stunning vistas of the Val d’Orcia, Pienza is a photographer’s dream. Here, you’ll get about an hour to explore on your own, soaking in the artistic architecture and local Pecorino cheese traditions.

Michelle M. appreciated the free time in Pienza, noting it as “a perfect combination of architectural beauty and harmony.” You might find yourself wandering the narrow streets, discovering quaint shops, or simply enjoying the views of the rolling hills.

The Scenic Drive and Overall Experience

Throughout the day, you’ll travel through some of Tuscany’s most iconic landscapes, including the UNESCO World Heritage site of Val d’Orcia. The tour’s vehicle is comfortable and air-conditioned, perfect for the roughly 8-hour journey. The small group size ensures you won’t be lost in a crowd, and the personal attention from your guide, Moro, is highly praised.

Many reviews mention how knowledgeable and friendly Moro is, going above and beyond—such as dropping guests closer to their hotels or customizing the day to suit interests. His expertise makes the difference between a good tour and a truly memorable one.

Analyzing the Value

At $218.70, this tour offers exceptional value—covering transportation, expert guiding, two wine tastings, a full Tuscan lunch, and entrance to historical sites, all in one day. Compared to the cost of visiting wineries independently, paying for tastings, and arranging transportation, it’s a smart choice. Plus, the intimacy of small groups means you’ll have more time to ask questions and learn about the experience.

The inclusion of Balsamic vinegar and extra virgin olive oil tastings adds a further layer of flavor and authenticity, giving you a comprehensive taste of regional products.

Who Will Love This Tour?

This experience is perfect for travelers seeking a personalized and relaxed way to experience Tuscany’s wine culture and scenic towns. It suits those who appreciate authentic, boutique wineries rather than commercialized tours. Wine lovers will especially enjoy tasting top-tier Brunello and Chianti, while history buffs will value the underground cave and Siena’s medieval charm. However, if you prefer more free time or a leisurely pace, you might find this tour somewhat packed, but for most, it hits a sweet spot.

The Sum Up

This small-group tour from Siena provides a rich blend of history, scenery, and wine in Tuscany. With expert guidance, intimate winery visits, and free time in Pienza, it’s well suited for those who want a balanced, authentic experience without the hassle of planning every detail.

You’ll love the stunning vistas, delicious Tuscan cuisine, and the chance to taste world-class wines in boutique settings. The itinerary’s thoughtful pacing and the guide’s knowledge ensure you’ll leave with a deeper appreciation for Tuscany’s cultural and vinicultural treasures.

For travelers who value small groups, local authenticity, and a well-rounded day exploring the heart of Tuscany, this tour is hard to beat. It’s particularly ideal for those wanting to combine history, scenery, and wine into one memorable experience.

FAQ

Is transportation included?
Yes, round-trip transfers from Siena are included, making it a smooth, hassle-free day without worrying about driving or parking.

How long is the tour?
The whole experience lasts approximately 8 to 9 hours, giving you plenty of time to enjoy each stop without feeling rushed.

What’s the group size?
The tour is designed for small groups, with a maximum of 6 travelers, ensuring a more personal and relaxed atmosphere.

Are meals included?
Yes, a Tuscan lunch with homemade pasta, Pecorino cheese, cold cuts, and bruschetta is included.

What wines will I taste?
You will sample Brunello di Montalcino, Chianti Classico, Super Tuscans, and Rosé wines at two boutique wineries.

Can I explore Pienza at my own pace?
Absolutely. The tour includes around an hour of free time in Pienza to walk, shop, or enjoy the views.

Are entrance fees included?
Admission to Siena’s underground cave and winery cellars is included; there are no additional museum tickets required.

Is this tour suitable for all fitness levels?
Yes, but travelers should have moderate physical fitness as some walking and stairs at wineries and towns might be involved.

This tour offers a wonderful way to truly taste and see Tuscany in a day—an experience packed with authentic moments, stunning landscapes, and memorable wines. Whether you’re a wine enthusiast, history lover, or simply seeking a beautifully curated day out, this trip from Siena is a fantastic choice.