VIP Chianti, Brunello wine & Pienza with lunch From Siena

Introducing the VIP Chianti, Brunello Wine & Pienza Tour from Siena

If you’re looking for a way to experience Tuscany’s quintessential charm without the hassle of planning, this small-group tour might just be your ticket. It offers a well-rounded day exploring two of Italy’s most famous wine regions—Chianti and Montalcino—alongside the stunning town of Pienza. What sets this tour apart is its focus on authenticity, intimate group size, and a tailored experience that many larger tours can’t match.

Two features we particularly love are the personalized attention, thanks to a maximum of six travelers per group, and the chance to visit boutique wineries where you can learn the secrets behind world-class wines like Brunello di Montalcino. Plus, the included lunch and tastings make this a true gastronomic journey.

If you prefer a structured day with some flexibility, this tour hits the mark. However, keep in mind that the full itinerary involves a fair bit of driving and walking, so it’s best suited for those with moderate mobility who love wine, scenic landscapes, and authentic local towns. It’s a great choice for couples, small groups of friends, or solo travelers craving a personalized taste of Tuscany.

Key Points

• Small-group experience ensures intimacy and personalized attention.
• Expert guides enhance the journey with local knowledge and stories.
• Tasting at boutique wineries provides authentic insights into Tuscany’s wine-making traditions.
• Flexible free time in Pienza allows for spontaneous exploration or relaxing.
• All-inclusive transportation makes for a hassle-free day.
• Exceptional reviews confirm this tour exceeds expectations with a perfect 5-star rating.

An In-Depth Look at the Tour Experience

Starting in Siena: A Historic Introduction and Hidden Secrets

Your day begins in Siena, a city rich with medieval charm and vibrant history. The guide, a licensed expert, will introduce you to Siena’s storied past, setting the stage for the day ahead. A highlight here is a visit to a secret underground medieval cave dating back to 600 BC. This underground site offers a tangible link to the city’s ancient roots and provides a cool, mysterious contrast to the bustling streets above.

This initial stop is free but offers fascinating insights that add depth to your Tuscany experience. Several reviewers raved about the guide’s knowledge, noting that this introduction made the whole day feel more meaningful. For example, Michelle called her day “an absolutely perfect day,” emphasizing how Morad’s friendly and insightful guidance made all the difference.

Castellina in Chianti: Boutique Wineries with a View

The next stop takes you to Castellina in Chianti, a picturesque town surrounded by rolling hills. Here, you’ll visit a family-owned organic boutique winery established in 1904, which offers an intimate look into traditional Chianti winemaking. The atmosphere is authentic, far removed from large commercial vineyards—more like visiting a friend’s cellar.

Expect to explore cellars dating back to the 1500s and sample some of Tuscany’s best wines. The tasting is complemented by a delicious Tuscan lunch featuring homemade pasta, Pecorino cheese, cold cuts, and bruschetta. This is where the tour truly shines—local flavors paired with exceptional wines, all in a setting that feels both luxurious and genuine.

We loved the way the guide shared stories behind each wine and the family’s history, making the tasting more personal. Reviewers like Michelle expressed that both wineries were “amazing,” and many highlighted how the intimate setting enhanced their appreciation for the region’s wine traditions.

Montalcino: Brunello and Breathtaking Views

The journey continues to Montalcino, home of the legendary Brunello di Montalcino wine. You’ll visit a family-owned boutique winery with views sweeping over the valley—these vistas alone are worth the trip. Here, you’ll learn about the secrets of Brunello production, tasting one of the world’s most celebrated wines, listed as the best wine in the world in 2024.

The winery visit includes cellar exploration and tasting, giving you a true sense of what makes Brunello so special. Several guests, including Alan G, highlighted the “exceptional guide” and how the tour was customized to include more time in the areas they most wanted to see.

Val d’Orcia and the Film Connection

Driving through the rolling hills, you’ll enjoy views that have captured imaginations for centuries. The Val d’Orcia, a UNESCO World Heritage site, is not only a feast for the eyes but also a film star—many scenes from “Gladiator” were shot here. The landscape’s soft contours and iconic cypresses create classic Tuscan scenery, perfect for those Instagram moments.

Pienza: Renaissance Charm and Pecorino

Your final stop is Pienza, often called the “touchstone of Renaissance urbanism.” This small town packs a punch with its harmonious architecture, lovely streets, and breathtaking vistas of the Val d’Orcia. It’s the perfect place to stretch your legs, explore on your own, and maybe indulge in some Pecorino cheese—Pienza’s most famous product.

Guests like Sarah appreciated the “impressive landscape” and the chance to wander freely. The hour allocated allows for leisurely exploration or a quick coffee before the day ends.

What’s Included and What to Expect

This tour offers excellent value, especially considering the all-inclusive nature. You’ll sip on Brunello di Montalcino, Chianti Classico, Super Tuscan, and Rosé wines across two wineries, with additional tastings of balsamic vinegar and extra virgin olive oil. The air-conditioned vehicle is comfortable, and with a maximum of six travelers, you get personal attention and flexibility.

The lunch in Castellina is substantial and authentically Tuscan—filled with homemade pasta, cheeses, cold cuts, and bread. The guide’s knowledge enriches every aspect, from the history to the wine secrets, making the experience more meaningful than just a tasting.

Timing and Group Size

Starting at 10 a.m., the 8- to 9-hour day is well-paced, with enough time at each stop to appreciate without feeling rushed. The small-group size means more interaction with the guide, personalized recommendations, and a quieter, more relaxed environment compared to larger coach tours.

Price and Value

At $218.70 per person, this tour offers a well-rounded day of wine, scenery, history, and authentic Tuscan cuisine. Several reviews note how the guide’s friendliness and the tour’s intimate style make it feel like a special day with friends rather than a commercialized experience.

Authenticity, Comfort, and Personal Touches

Travelers consistently praise the knowledgeable guides who make the history come alive and share personal insights. Morad, the guide, receives special mention for his friendliness, flexibility, and vast local knowledge. Several reviews highlight how he accommodated requests and created a customized experience, exceeding expectations.

Comfort is also a priority, with a private, air-conditioned vehicle ensuring a smooth ride through Tuscany’s scenic roads. The small group enhances this feeling of intimacy, allowing for spontaneous stops or more in-depth conversations.

Who Will Love This Tour?

This experience is perfect for wine lovers, those who appreciate authentic small wineries, and travelers who want a personalized, relaxed day in Tuscany. It suits people interested in history, scenic landscapes, and local cuisine—and who prefer traveling with a small, friendly group rather than a large bus. It’s especially attractive to those who value guides who share stories and insights rather than just logistics.

If you’re a traveler craving a deliberately paced, high-quality, and local experience, this tour delivers.

Final Thoughts: A Day Well Spent in Tuscany

This VIP tour offers an excellent balance of wine, scenery, history, and food—all within an intimate setting that allows for genuine connection and personalized experiences. The focus on boutique wineries and authentic towns like Pienza ensures you get more than just touristy photo ops; you’ll walk away with a deeper appreciation for Tuscan culture and craftsmanship.

The value for money is evident when you consider the included tastings, lunch, and personalized attention. While it involves a full day of travel and exploration, the pace is comfortable, and the scenery along the way makes every minute worthwhile.

In short, this tour is a fantastic choice for those who want a meaningful, relaxed, and delicious taste of Tuscany—especially if you prefer small-group experiences that feel both exclusive and genuine.

FAQ About the Tour

Is transportation included in this tour?
Yes, all round-trip transfers are included, and you’ll travel comfortably in an air-conditioned vehicle designed for small groups.

How many people will be on the tour?
The tour is limited to a maximum of six travelers, ensuring a more intimate and personalized experience.

What kind of wineries will I visit?
You’ll visit two boutique wineries, one in Chianti and the other in Montalcino, both family-owned and focused on organic practices and authentic production.

Is lunch provided?
Yes, the tour includes a Tuscan lunch featuring homemade pasta, Pecorino cheese, cold cuts, and bruschetta, paired with wine tastings.

Can I explore Pienza on my own?
Absolutely. The itinerary provides about an hour of free time in Pienza, allowing you to wander, shop, or relax at your own pace.

What’s the best time to book this tour?
It’s recommended to book well in advance—about 81 days ahead on average—to secure your spot, especially during peak season.

To sum it up, this small-group VIP tour from Siena offers a well-curated blend of history, wine, scenery, and local flavor. It’s best suited for travelers seeking a personalized and authentic Tuscan experience, leaning towards wine connoisseurs, curious explorers, and anyone eager to savor the true spirit of Italy’s beloved countryside.