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Discover Tuscany’s highlights on this Val d'Orcia Brunello Wine Tour from Florence, including visits to Montalcino, Pienza, and Montepulciano with wine tastings and scenic views.
The Val d’Orcia Brunello Wine Tour with Montalcino, Pienza, and Montepulciano offers an immersive day in Tuscany’s most iconic spots. For $265.31 per person, this guided journey takes approximately 10 hours 30 minutes, providing a comprehensive experience of the region’s celebrated wines, charming towns, and breathtaking landscapes. The tour departs from Florence at 8:00 AM, traveling in a premium air-conditioned minivan with an English-speaking driver, ensuring comfort and ease throughout the day.
This tour is limited to eight travelers, making it a semi-private experience that balances personalized attention with the camaraderie of a small group. It’s highly recommended—by 90% of those who book—for its quality, in-depth visits, and scenic stops. While the tour includes wine tastings, a superior lunch, and guided tours of vineyards, cellars, and the underground city of Montepulciano, some reviews mention that the lunch and sightseeing time can feel tight, especially for exploring the towns in depth.


The journey begins early at 8:00 AM with your English-speaking driver in Florence. The first stop arrives in Montalcino around 9:45 AM, where a local family-owned winery welcomes you. This visit feels more like a warm homecoming than a typical winery tour, with guides sharing details about Brunello di Montalcino’s vineyard techniques, aging process, and vintages.
The 1.5-hour visit includes a guided wine tasting in a setting full of character. You’ll learn how Brunello di Montalcino is crafted and appreciated, with the opportunity to taste different vintages. Afterward, there’s a brief 15-minute stop at the Fortezza di Montalcino, a castle with a tiny city center, offering a quick glimpse of the historic fortress and scenic views.
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At 12:15 PM, the tour moves to Pienza, a UNESCO World Heritage Site famous for celebrated Pecorino cheese. Here, a superior lunch takes place in an XV-century ex-convent, with outdoor seating that offers spectacular views of the Val d’Orcia (from April to October). The meal includes three courses, wine, and water—though in winter, the lunch is served indoors.
After enjoying the meal, guests have about an hour and a half to explore Pienza at their own pace. The charming streets, viewpoints behind the cathedral, and cheese shops are highlights. This free time allows for shopping or simply soaking in the peaceful atmosphere of this beautifully preserved town.
In the afternoon, the tour continues to Montepulciano around 2:45 PM. Here, an expert-guided tour of “The underground city” takes visitors into a historic cellar located beneath a local wine shop. This guided walk offers insights into Nobile wine production and wine aging techniques.
Following the underground tour, guests are treated to a wine and food tasting that includes local specialties. The main square in Montepulciano, perched atop the town, provides a perfect spot for photos before the group heads back toward Florence around 6:30 PM.

The trip uses a premium van equipped with A/C, ensuring a comfortable ride throughout the day. The driver is an English speaker but is not a guide, so the focus is on safe, smooth transportation. The meeting point is at Piazza degli Antinori in Florence, with the tour ending back at the same location.
With a maximum of eight travelers, the tour offers a more personalized experience. It is highly recommended to book about 63 days in advance, given the limited spots and popularity.
Guests enjoy two wine tastings—featuring Brunello and Vino Nobile—plus a guided tour of vineyards and barrels. The lunch, with views in warmer months, is a notable highlight, though some reviews mention that the food can be basic or that the time spent exploring the towns might be limited.

The small group format ensures a more relaxed and personalized experience, especially during vineyard visits and tastings. The guided cellar tours provide an educational edge, making the wine tastings more meaningful. The scenic drive through the Val d’Orcia, a UNESCO site, showcases classic Tuscan landscapes that have inspired painters and photographers alike.
Many reviews praise the driver’s friendliness and knowledge, highlighting guides like Sal and Mike for their attentiveness and storytelling. Their local insights and patience contribute significantly to the positive experiences.
The lunch with panoramic views in Pienza is frequently described as a memorable part of the tour, with delicious food and a relaxing ambiance. The wine tastings are consistently praised, especially for the quality of Brunello and Nobile wines. Several reviews highlight that the wineries are informative, friendly, and offer excellent tastings.
Some guests note that the timing can be tight, especially in terms of exploring Pienza and Montepulciano on their own. The lunch in winter may lack the outdoor views available in warmer months, and the van’s capacity can make the ride slightly cramped if not traveling with a small group.

This day trip from Florence balances wine tasting, scenic views, and charming towns in one memorable package. Its small group size and guided vineyard visits make it ideal for wine enthusiasts and those seeking an intimate experience of Tuscany’s landscapes.
The included tastings, guided tours, and lunch offer good value, especially for those interested in Brunello and Vino Nobile wines. While the pacing may feel rushed for some, the overall experience delivers a comprehensive taste of Tuscany’s culture, cuisine, and viticulture.
Those who enjoy learning about wine production, photographing beautiful scenery, or simply relaxing in Tuscan villages will find this tour particularly rewarding. It is best suited for small groups looking for an informative yet leisurely day away from the crowds.
“We loved our guide. The tour was beautiful. Learned much. The only thing is because the wine is available in the States. I spent a lot of money to …”

How early does the tour start?
The tour departs from Florence at 8:00 AM.
What is the duration of the tour?
The entire experience lasts approximately 10 hours and 30 minutes.
What locations are visited on this tour?
Stops include Montalcino, Pienza, and Montepulciano.
Are meals included?
Yes, a superior three-course lunch with wine and water is included in Pienza, seasonally available.
How many people are in the group?
The tour is limited to eight travelers for a semi-private experience.
What wines are tasted?
Guests taste Brunello di Montalcino and Vino Nobile during the visits.
Is transportation comfortable?
Yes, the premium van with A/C provides a comfortable ride throughout the day.
Are the visits guided?
Yes, guides lead you through vineyard, cellar, and underground city tours.
Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the start.
Who operates this tour?
The experience is provided by Keys Of Italy / Florence.
For more details or to book, visit the official site linked in the source.