VIP Chianti, Brunello wine & Pienza with lunch From Siena

Discover Tuscany with an Intimate VIP Tour from Siena

This VIP Chianti, Brunello wine & Pienza with lunch tour offers an immersive day in Tuscany, combining wine tastings, historic towns, and stunning landscapes. Priced at $218.70 per person, it promises an intimate experience with a small group of 6 or fewer travelers, ensuring personalized attention. Departing from Siena at 10:00 am, the tour lasts approximately 8 to 9 hours, and all transport is included, making for a relaxed and hassle-free day.

What sets this tour apart is the focus on boutique wineries, with visits to two family-owned wineries—one in Chianti and another in Montalcino—where top-quality wines like Brunello di Montalcino and Chianti Classico are sampled. The itinerary also includes free time in Pienza to explore at your own pace, and a Tuscan lunch featuring homemade pasta, Pecorino cheese, and cured meats. With an average booking window of 81 days in advance, it’s a popular choice for those seeking a personalized Tuscan experience.

Key Points

• Small-group size (6 people or fewer) ensures a more personal experience
• Visits to two boutique wineries in Chianti and Montalcino with tastings and cellar tours
• Includes round-trip transport from Siena for convenience
• Tuscany lunch with homemade pasta, Pecorino, cold cuts, and bruschetta
• Exploration of Pienza, a Renaissance town known for its architecture and Pecorino cheese
• Tour led by a licensed guide, who shares insights into Tuscany’s history and wine secrets

Starting Point in Siena at Prosperino Bistrot

This tour begins at Prosperino Bistrot, located at Viale XXV Aprile, at 10:00 am. It features air-conditioned transportation in a vehicle that accommodates a maximum of 6 travelers, maintaining an intimate atmosphere. The guide, Morad, is praised for his knowledgeable and friendly manner, making the experience both educational and enjoyable.

The tour concludes back at the starting point later in the day, providing a seamless experience with minimal hassle. Travelers can expect moderate physical activity during walks at various stops and the chance to enjoy Tuscany’s scenery comfortably.

Exploring Siena’s Historic Roots and Underground Secrets

The tour kicks off in Siena with a licensed guide explaining the city’s history, including a visit to a hidden underground medieval cave dating back to 600 BC. This exclusive subterranean experience adds a layer of intrigue and offers insight into Siena’s past that few visitors get to see.

The 30-minute tour is free of charge and sets the tone for the day, blending history with the scenic beauty of Tuscany. This stop appeals to those interested in medieval architecture and hidden historical sites, making it a great starting point for the day.

Visiting Castellina in Chianti: Organic and Family-Owned

Next, the group heads to Castellina in Chianti, home to an organic boutique winery established in 1904. This family-owned vineyard offers a breathtaking view over the rolling Tuscan hills, perfect for photo opportunities. Visitors enjoy a cellar tour dating back to 1500, gaining insight into wine-making traditions passed down through generations.

The highlight here is the wine tasting, which includes Chianti Classico and other top wines, complemented by a Tuscan lunch featuring pecorino cheese, cold cuts, and homemade pasta. The two-hour visit allows ample time to relax, taste, and appreciate the serene landscape that makes Chianti so renowned.

Brunello di Montalcino: A Top-World Wine Experience

In Montalcino, the tour visits a family-owned boutique winery famous for its Brunello di Montalcino, which was awarded the title of best wine in the world in 2024. The visit includes a tour of the cellars and an opportunity to learn all the secrets behind Brunello production.

The tasting session lasts about an hour and provides an opportunity to sample this prestigious wine against the backdrop of breathtaking valley views. This stop is ideal for wine enthusiasts interested in high-quality Brunello and learning about its unique aging process.

Scenic Drive through Val d’Orcia and the Film-Set Views

The journey features a scenic drive through the Val d’Orcia, a UNESCO World Heritage Site, famous for its rolling hills and iconic landscapes. Travelers enjoy views that include scenes from the movie “Gladiator”, making this segment a photographer’s dream.

While no specific activity is scheduled here, the drive offers a chance to relax and take in the classic Tuscan scenery, often considered the most picturesque landscape in the region.

Pienza: The Renaissance Artistic Jewel

The last stop is Pienza, a Renaissance town celebrated for its harmony of architecture and landscape. Known as the “Touchstone of Renaissance Urbanism,” Pienza is perfect for wandering freely and discovering its artistic charm.

The town’s most renowned tradition is Pecorino cheese, which visitors can sample or purchase. With about an hour of free time, guests can stroll the quaint streets, admire impressive architecture, and soak in the breathtaking views over Val d’Orcia.

Exclusive Tastings and Culinary Highlights

Throughout the day, the tour offers exclusive tastings of organic balsamic vinegar and extra virgin olive oil, enhancing the culinary experience. The lunch is a highlight, featuring homemade pasta, Pecorino cheese, ham, salame, and bruschetta, all served in a traditional Tuscan setting.

These food and drink tastings showcase the region’s local craftsmanship, giving travelers a taste of authentic Tuscan flavors paired with world-class wines.

The Guide and Group Experience

Many reviews highlight Morad, the guide, whose knowledgeable, friendly, and accommodating approach elevates the day. The small group size ensures ample time for questions, personalized attention, and a relaxed pace. Guests appreciate the flexibility, like Morad’s willingness to customize the itinerary and drop off closer to the hotel.

The entire experience is crafted to be informative yet leisurely, with plenty of time to explore each location at a comfortable pace. This tour is perfect for those who enjoy a personalized, less crowded way** of experiencing Tuscany’s highlights.

Final Thoughts on the VIP Chianti, Brunello, and Pienza Tour

This tour from Siena offers a well-balanced itinerary that combines historic sites, world-class wines, and picturesque towns. The small-group format guarantees a more personalized experience, with high praise for the guide’s expertise and friendliness. The inclusion of lunch, tastings, and exclusive cellar visits makes it a great value at $218.70.

While the tour involves some walking and moderate physical activity, it remains accessible for most guests. Its focus on boutique wineries and artistic towns makes it especially appealing to wine lovers, history buffs, and those seeking a more intimate way to enjoy Tuscany’s beauty.

Frequently Asked Questions

How long is the tour?
The tour lasts approximately 8 to 9 hours, starting at 10:00 am and ending back in Siena later in the day.

What is included in the price?
The price covers round-trip transport, visits to two boutique wineries, wine tastings, a Tuscan lunch, exclusive cellar tours, and tastings of balsamic vinegar and olive oil.

Are there any additional costs?
Museum tickets are not included in the price. Guests should budget separately if they wish to visit any museums or additional attractions.

What is the group size?
The tour is limited to 6 travelers or fewer, ensuring an intimate, personalized experience.

Is the tour suitable for all physical fitness levels?
Yes, the tour involves some walking, but it is generally suitable for travelers with moderate physical fitness.

Can the tour be customized?
Yes, reviews mention that guides like Moro are accommodating and willing to customize the experience based on guests’ interests.

What stops are included in the itinerary?
Stops include Siena, Castellina in Chianti, Montalcino, the drive through Val d’Orcia, and Pienza.

Is lunch included?
Yes, the Tuscan lunch featuring homemade pasta, Pecorino cheese, ham, and bread is included.

Can I explore towns on my own?
Yes, the tour includes free time at Pienza for personal exploration.

What is the main highlight of this tour?
The combination of wine tastings at boutique wineries, historic towns, and scenic landscapes makes this a memorable way to experience Tuscany in one day.