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Experience Siena's underground medieval aqueduct with a 75-minute wine tasting of Brunello, Chianti, and Super Tuscans paired with local cheese for $75.15.
A unique wine tasting experience awaits in Siena, Italy, at a price of $75.15 per person. This 1 hour and 15-minute tour takes place beneath the historic city in an authentic medieval aqueduct dating back to 600 BC. Guided by a certified sommelier, visitors explore a private underground cave filled with brick vaults and stone tunnels, offering an unforgettable setting to sample some of Italy’s best wines, including Brunello di Montalcino, Chianti Classico, and Super Tuscan selections. The tour also includes local pecorino cheese and snacks, making it a flavorful journey into the region’s wine culture.
Ideal for wine enthusiasts and those curious about Siena’s history, this experience balances educational insights with delicious tastings in a small group setting. With many reviews rating it a perfect 5, it clearly resonates with visitors for its atmosphere, knowledge, and exclusivity. The tour departs from Via del Paradiso, 54, conveniently close to Siena’s Cathedral, making it easy to combine with sightseeing adventures.


This tour centers on an ancient aqueduct, a secret subterranean space hidden beneath Siena’s historic core. Built around the time of 600 BC, the cave features brick vaults and tunnels carved directly into the stone. Visitors walk through this fascinating structure, gaining a sense of Siena’s long-standing engineering ingenuity and medieval history. The atmosphere of the underground chamber adds a layer of ambiance that enhances the wine tasting, making it more than just a simple event.
The location near San Domenico offers fantastic views over Siena and the Basilica, providing a scenic walk before descending into the historic cellar. The private access in such a significant archaeological site ensures that the experience feels intimate and exclusive. Most reviews highlight how the historical setting makes this tour truly special compared to standard wine tastings.
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Guests will sample a curated selection of wines that include Brunello di Montalcino, Chianti Classico, and Super Tuscan options. The Brunello di Montalcino, recognized by Spectator Magazine as a top 10 wine, is served alongside pecorino cheese and snacks, providing a perfect pairing. The Super Tuscan wines bring a modern twist to traditional flavors, showcasing the diversity of Siena’s vineyards.
The guide, a certified sommelier, explains the nuances of each wine, offering insights into vintage differences and regional characteristics. Multiple reviews mention the high quality of wines and how the guide’s knowledgeable narration enhances understanding. For wine lovers, this focused tasting offers an educational edge that elevates the experience beyond casual sipping.

Frederico, or the guides involved, are consistently praised for their enthusiasm, expertise, and friendly approach. Reviewers note that Frederico’s storytelling makes the experience engaging and informative. He shares fascinating facts about Siena’s history and the discovery of the crypt, making the tour both educational and entertaining.
The small group size (up to 13 guests) allows for personalized attention, which many reviews highlight as a major plus. Visitors appreciate how the guide balances technical wine knowledge with friendly conversation, creating a warm and welcoming environment.

The tour begins at Via del Paradiso, 54, close to the Siena Cathedral. The location’s proximity makes it easy for visitors to incorporate this activity into their city sightseeing. The tour is suitable for most travelers, as it is rain or shine and most people can participate, provided they are 18 years or older.
Accessibility is noted with service animals allowed, and the tour’s duration makes it manageable for a wide range of visitors. The small group format ensures an intimate experience, and the mobile ticket feature allows for straightforward check-in.

This experience’s main appeal lies in its setting. The brick vaults and stone tunnels evoke a genuinely medieval ambiance, transporting guests back in time as they enjoy their wine tasting. The cave’s history adds an extra layer of cultural richness, with many reviews mentioning how the atmosphere enhances the wine.
The lighting and architecture contribute to a romantic, warm environment where guests can relax and savor the wines. Many visitors mention that the cave’s uniqueness makes this tasting more memorable than a typical vineyard visit.
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Priced at $75.15 per person, this tour offers a competitive price considering the exclusive access to a medieval underground space, the premium wines, and the expert guidance. Most reviews agree the experience is well worth the cost, especially given the quality of wines and the atmosphere.
The booking window is approximately 54 days in advance, indicating high interest. The tour includes all tastings and cheese, with free cancellation available if canceled more than 24 hours before the scheduled time. This flexibility adds to the tour’s value proposition for visitors planning their trip.

This wine tasting in Siena’s underground cave is perfect for wine enthusiasts, history buffs, and adventurers seeking a distinctive experience. It suits those who appreciate authentic settings and want a personalized and educational introduction to Tuscan wines.
It’s especially ideal for visitors who enjoy small-group environments and guided storytelling about local culture and history. The heightened atmosphere makes it a great activity for couples, small groups of friends, or solo travelers looking for an enriching, flavorful experience.
“This was a unique and fun experience. Frederick was so knowledgeable and fun to talk to. Definitely recommend this event.”

How long does the wine tasting last?
The tour runs for approximately 75 minutes, including the walk to and from the underground cave.
Where does the tour start and end?
It begins at Via del Paradiso, 54 and ends back at the same location, making it easy to continue sightseeing afterward.
Is the tour suitable for children?
No, the minimum drinking age is 18 years old, but most other visitors can participate easily.
What wines are sampled during the tour?
Guests enjoy Brunello di Montalcino, Chianti Classico, and Super Tuscan wines.
Are food options included?
Yes, pecorino cheese and snacks are provided to complement the wines. Bruschetta is no longer available.
Can I cancel the tour if my plans change?
Yes, free cancellation is available if canceled more than 24 hours before the start.
Is the cave accessible for everyone?
The tour is suitable for most travelers, with most participants able to access the underground space, and service animals are permitted.
How far in advance should I book?
Most bookings are made around 54 days in advance, so early reservations are recommended for guaranteed availability.
What makes this tour different from a vineyard visit?
The underground medieval setting and historical atmosphere offer a more intimate and distinctive experience than traditional vineyard tours.
Is the tour suitable if I already know about wine?
Yes, the expert guides provide insights into regional wines and discussions on aging and vintage variations, enriching even seasoned wine lovers’ understanding.
Can I combine this with other Siena sightseeing activities?
Absolutely; its location near Siena’s Cathedral makes it easy to add to a day of exploring the city’s historic sites.
This Siena Underground Wine Tasting offers a blend of history, culture, and wine in a medieval setting that few other experiences can match. Highly rated and uniquely atmospheric, it appeals most to those seeking a personalized, educational, and delicious journey into Tuscany’s wine heritage.