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Discover the charm of Tuscany with this small-group Brunello di Montalcino wine tour from Siena, featuring visits to three wineries, a delicious Tuscan meal, and an historic abbey.
Exploring Tuscany’s renowned wine region becomes a seamless and memorable experience with the Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena. Priced at $213.29 per person, this approximately 9-hour journey offers an intimate look into the world of Brunello di Montalcino, one of Italy’s top wines. The tour’s small-group size—maximizing at 8 travelers—ensures personalized attention and a relaxed atmosphere, perfect for wine enthusiasts and curious newcomers alike.
The trip begins with a convenient pickup in central Siena, where a friendly guide introduces you to the lush Tuscan hills. Over the course of the day, you’ll visit three distinct wineries, including a family-run estate and a small boutique winery, giving you a genuine taste of local wine craftsmanship. The itinerary includes tasting a variety of wines, enjoying a generous Tuscan lunch, exploring Montalcino town, and visiting the awe-inspiring Abbey of Sant’Antimo—making this a well-rounded experience for lovers of wine, history, and scenic views.

Travel starts at Piazza San Domenico in central Siena. A comfortable, air-conditioned minivan transports you across the rolling Tuscan countryside to Montalcino. The journey offers scenic views, setting the perfect tone for a day dedicated to wine and landscape. With a mobile ticket feature, the process remains smooth, and the group size retains an intimate feel.
The guide leads you through each stage of the day, providing insights into the region’s viticulture and history. This trip emphasizes leisurely pacing, allowing plenty of time at each stop for tasting, exploring, and relaxing.
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The day begins at a small winery, where you will walk among vineyards and tour the cellars with your guide. Swirling and sipping Brunello di Montalcino, you’ll learn about the wine’s production process and what makes it so special. The cellars provide a behind-the-scenes look at how Brunello is aged, adding depth to the tasting experience.
This stop is especially appreciated for avoiding tourist trap wineries; instead, it offers authentic, non-commercial settings, often in homes of local owners. The relaxed environment encourages genuine conversations with the hosts and an appreciation for local craftsmanship.

After the initial winery visit, you arrive in Montalcino, a charming hilltop town famous for its wine production. The town offers free time to explore independently—browse boutique shops, admire the panoramic views of the Val d’Orcia, or simply sip more wine at local cafes.
This break provides a chance to soak in the authentic Tuscan atmosphere, away from overcrowded tourist spots. Many appreciate the opportunity to walk through the narrow streets and take in the spectacular landscape that surrounds the town.

The highlight for many is the lunch at a family-run winery, where winemakers warmly welcome guests. The meal features antipasti, pasta or risotto, and dessert, all crafted with typical Tuscan flair. The lunch is served alongside generous pours of local wines, making each bite and sip a celebration of regional flavors.
Guests rave about the homemade quality of the food, and the informal atmosphere fosters engaging conversations with the hosts. This is not just a meal; it’s an immersive experience in Tuscan hospitality and culinary tradition.

A short drive takes you to the Abbey of Sant’Antimo, a medieval Benedictine monastery. Your guide explains the history and architecture of the site, which has a peaceful and spiritual ambiance. Visitors often get the chance to hear Gregorian chants sung by the monks, adding a memorable, ethereal layer to the visit.
This stop provides a tranquil contrast to the wineries, offering insight into religious architecture and the spiritual history of the region. The abbey’s stunning structure and serene setting make it a favorite among visitors seeking quiet reflection and beautiful scenery.
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The last stop of the day is at a third winery, where a production lesson is offered—covering winemaking techniques, aging processes, and bottle aging specifics. You get to sit down for a final tasting, sampling Brunello di Montalcino along with other wines from the estate.
This session consolidates your understanding of what makes Brunello distinctive, and many find the wines to be exceptionally good—a perfect finale to the day’s journey.
Throughout the trip, guides such as Paolo, Georgia, and others, showcase remarkable knowledge and personable styles. They share stories, history, and details about each winery, making the experience both educational and engaging. Many reviews highlight guides as key to the tour’s success, praising their English fluency, passion, and attention to detail.
The guides also take care of logistical details, ensuring the pace remains leisurely and the group size stays small for intimacy. Their enthusiasm and hospitality significantly enhance the overall experience.

This tour operates from Piazza San Domenico at 9:30 am and does not include hotel pickup and drop-off. It’s suitable for most travelers, with most participants able to join. The tour is not recommended for minors under 18 years old due to wine tastings.
The air-conditioned vehicle ensures comfort, and the mobile ticket makes for easy access. Travelers should be aware that the tour’s pacing is relaxed, allowing plenty of time for tasting and exploring but not enough for extensive walking or strenuous activity.
What sets this tour apart is its focus on authentic wineries and personal stories from the owners, thanks to visits that avoid tourist traps. The inclusion of a home-style lunch and the visit to Sant’Antimo Abbey enrich the experience beyond just wine tasting.
The small-group format and knowledgeable guides turn a simple wine tour into an immersive cultural experience. Many reviews mention guides like Georgia, Daniele, and Guillermo as making the day memorable with their passion and stories.
This $213.29 tour offers a well-balanced day of wine, food, and scenery. It caters especially to those who want to learn about Brunello di Montalcino in an authentic setting, paired with Tuscan hospitality. The visits to three wineries, including a family-run estate, make it a great choice for wine lovers seeking genuine local experiences.
While it doesn’t include hotel pickup, the central Siena meeting point and smooth logistics make it simple to join. The small-group size ensures an intimate and relaxed atmosphere, ideal for anyone wanting a personalized and informative tour of Montalcino’s remarkable wines.
“Cannot recommend this tour enough. We visited 4 cities in Italy, and this was by far the favorite activity of the entire trip by everyone. The wine…”
Is hotel pickup included in this tour?
No, the tour does not include hotel pickup or drop-off. Participants meet at Piazza San Domenico in Siena at 9:30 am.
What is the maximum group size?
The tour limits to 8 travelers, providing a more personalized experience.
Are children allowed to join?
Children under 18 years old are not served alcohol, but the tour’s activity level is suitable for most adults.
What should I wear for the winery visits?
Casual, comfortable clothing is recommended, especially since there are vineyard walks and cellar tours.
Can I cancel this tour?
Yes, there is a free cancellation policy available up to 24 hours in advance for a full refund.
What makes this tour stand out?
The authentic wineries, delicious Tuscan lunch, and knowledgeable guides make this tour a favorite among those seeking genuine local culture.
How long does the tour last?
Approximately 9 hours, offering plenty of time for tasting, sightseeing, and relaxing.
Is this tour suitable for wine beginners?
Absolutely—guides provide educational insights that enhance the tasting experience, perfect for those new to wine.
What is included in the tour price?
The wine tastings, lunch, guided visits, and transportation are included. Hotel transfers are not.
Will I get to taste Brunello di Montalcino?
Yes, multiple tastings at various wineries focus on Brunello di Montalcino, along with Rosso and other regional wines.
Where do the visits take place?
You visit three wineries—including a small winery, a family-run estate, and a production-focused winery—plus the Abbey of Sant’Antimo.
This detailed review highlights the authentic charm, personalized experience, and delicious wines that define this small-group Brunello tour from Siena. It’s a perfect choice for anyone eager to explore Montalcino’s wine culture in an intimate and enriching way.