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Discover Montalcino's best with this tour featuring two wine tastings, a historic cellar visit, and stunning views of Val d’Orcia. Perfect for wine lovers.

This tour offers a well-rounded experience of Montalcino, combining two tastings of the world-famous Brunello di Montalcino with a visit to a centuries-old cellar tucked inside the town’s ancient walls. It’s designed for those who want to enjoy Italy’s iconic wine scene while soaking in the medieval charm and breathtaking scenery of the Val d’Orcia.
What really stands out are the insider insights from guides who are passionate and knowledgeable—most notably Sara, who received high praise for her friendliness and depth of wine and local history knowledge. Another highlight is the opportunity to explore a historic family cellar, which has been producing wine for over 20 generations. However, one thing to consider: the tour is quite full, with a packed itinerary that leaves little time for extra wandering or lengthy tastings.
This experience is ideal for wine enthusiasts, history buffs, and travelers seeking a taste of authentic Tuscany without breaking the bank. If you’re looking for an engaging, informative, and scenic day in Montalcino, this tour hits all the right notes.

Wine enthusiasts might appreciate these other Chianti tasting experiences

Our journey begins in a historic wine bar located right in Montalcino’s old town center. This spot is not only atmospheric but also perfectly positioned for a real taste of local life. Here, you’ll be welcomed with your first glass of Brunello di Montalcino, considered one of Italy’s most renowned wines. The guide explains the wine’s unique characteristics, including its aging process and what makes it so special globally.
A other standout feature is the wine card with a €5 value, allowing you to extend your tasting experience if something particularly piques your interest. This flexibility means you can sample additional vintages or styles if you wish, adding to the personalized nature of the outing.
Reviewers like Adam praised Sara’s friendly and insightful approach, emphasizing her ability to weave in stories of the region’s wine history while guiding tastings. For wine lovers, this tasting is more than just sipping; it’s an educational experience that deepens your appreciation for Brunello’s craftsmanship.
Next, the tour takes you into a historic cellar within Montalcino’s ancient walls. This is a rare chance to step into a family-run winery that has been producing wine for over 20 generations. The guide (Lucia, according to one review) makes the visit engaging by sharing stories of the family’s long history and the traditional techniques they’ve preserved.
The cellar itself is a visual treat—imagine stone walls, aged barrels, and the scent of wine that has traveled through centuries. The tasting here includes different vintages, giving you a sense of the progression and depth of the local wines. Reviewers like Bob praised the gorgeous setting and the knowledgeable guidance, noting that the view over the Val d’Orcia during the tasting made for a truly memorable moment.
After the cellar visit, you’ll have roughly four hours to wander the medieval streets of Montalcino using the included digital itinerary. This self-guided component is a fantastic tool, filled with maps, tips, and suggestions on what to see, taste, and buy. The town’s narrow alleys, quaint piazzas, and historic sights offer a delightful step back in time.
One reviewer remarked how the itinerary made their exploration stress-free, allowing them to enjoy hidden gems and local eateries without the fear of missing out. You might find small artisanal shops, charming cafes, or viewpoints offering sweeping vistas of the rolling Tuscan landscape—truly a feast for the eyes.
The final highlight is the second wine tasting at a city-center wine bar, where you get to explore the iconic Brunello di Montalcino further. Here, you can extend your tasting with the wine card and sample from a selection of vintages, gaining a broader understanding of the wine’s nuances.
The digital itinerary is an impressive bonus—full of maps, tips, and personalized recommendations—which enhances your overall day. This means you can tailor your exploration, focusing on what interests you most, whether that’s more wine, local food, or simply soaking in the scenery.
At $79.45 per person, the tour offers very good value, considering the inclusion of multiple tastings, a guided cellar visit, digital map, and transportation (if selected). The fact that it is a private tour—only your group participates—adds to the feeling of personalized attention.
The duration of 6 to 8 hours allows enough time to enjoy each aspect without feeling rushed. Plus, with the option for pickup and flexible cancellation (up to 24 hours in advance), it’s a convenient choice for most travelers.

This experience suits those who are genuinely interested in Tuscany’s wine heritage and want to learn from passionate guides. It’s perfect if you appreciate a mix of cultural, scenic, and culinary moments, and prefer a well-organized, intimate tour rather than a large, impersonal bus outing.
If you’re eager to discover hidden historic sites and get authentic, detailed insights into winemaking traditions, this tour will meet your expectations. It’s also a great choice for travelers who value value for money, as it combines multiple experiences into one affordable package.
This tour offers a comprehensive and authentic taste of Montalcino, blending top-tier wine experiences with cultural and scenic exploration. The guides’ knowledge and friendliness make a significant difference, turning what could be a simple tasting into a memorable journey into Tuscany’s heart.
The visit to the historic cellar stands out as a rare opportunity to see a family’s wine legacy unfold inside ancient walls. Meanwhile, the panoramic views over Val d’Orcia during the tastings provide a perfect backdrop for absorbing the true essence of the region.
For wine lovers, history enthusiasts, or anyone craving a relaxed, immersive day in one of Tuscany’s most charming towns, this experience offers great value and genuine insight.
Is transportation included?
Transportation is included if you select the option with transfer. Otherwise, the meeting point is in Montalcino, and you will need to arrange your own transport.
How long does the tour last?
The tour lasts approximately 6 to 8 hours, giving ample time for tastings, a cellar visit, and exploring Montalcino at your own pace.
Are the tastings extensive?
Yes, you will enjoy guided tastings of three wines at a historic winery, with the option to extend your experience at a central wine bar with a wine card worth €5.
Can I customize my tasting experience?
The digital itinerary allows you to explore Montalcino independently, but the actual wine tastings are included as part of the organized tour. You can extend tastings at the wine bar using your wine card.
Is this tour suitable for all ages?
While primarily designed for adults interested in wine and history, most travelers can participate. Minors might be limited from wine tastings, but can still enjoy the sights and scenery with a responsible adult.
What’s the significance of the cellar visit?
The cellar has been operated by a family for over 20 generations, making it a rare, authentic insight into traditional winemaking inside Montalcino’s historic walls.
Do I need to book in advance?
Yes, most travelers book about 84 days in advance, indicating high demand. Advance booking ensures availability and allows you to plan your trip smoothly.
Is there any lunch included?
No, lunch is not included. You might want to plan to enjoy local restaurants or cafes during your free time in Montalcino.
This tour combines the best of Montalcino’s wine heritage, scenic views, and historical charm—a wonderful way to deepen your appreciation of Tuscany’s treasured traditions.