Montepulciano is a town that practically breathes history — its winding streets, medieval architecture, and centuries-old wine cellars make it a perfect place for exploring the past. What sets Montepulciano apart from other Tuscan towns is its deep-rooted winemaking tradition, preserved underground in vaulted cellars carved into the rock. If you’re passionate about wine and history, one of these guided cellar tours will give you a richer understanding of the town’s heritage. We particularly like the Montepulciano: Historical Cellars Guided Tour & Wine Tasting for its comprehensive experience and great reviews, offering a perfect blend of cultural insight and delicious wine.
Below, you’ll find a list of the best historical tours in Montepulciano, each offering a unique look into the town’s cellar history, along with expert guides and memorable tastings.
1. Montepulciano: Historical Cellars Guided Tour & Wine Tasting

At number one, this tour shines with a 4.4-star rating from 81 reviews, making it a favorite for those who value depth and quality. The 2.5-hour experience takes you through two underground cellars in Montepulciano’s historic center, where you’ll learn about the centuries-old tradition of wine aging in brick vaults and oak barrels. The tour begins with a walk through the charming Piazza Grande, then descends into the tunnels carved into the tuff, revealing the caves that have stored and matured wine for generations. The guide, well-versed in local history, explains how these cellars supported Montepulciano’s fame as a wine hub.
What makes this tour stand out is the in-depth tasting of Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano DOC, giving a taste of the region’s finest. The guide’s storytelling enhances the experience, connecting the wine to the town’s story. This is an excellent choice for travelers seeking a well-rounded, engaging experience that combines history, culture, and excellent wine. The tour’s value lies in its balance of informative guidance and generous tastings, making it suitable for both wine aficionados and history lovers alike.
Bottom Line: Ideal for those wanting a detailed, expert-led exploration of Montepulciano’s underground wine cellars paired with tastings of top regional vintages.
2. Tour of the historical cellars in Montepulciano

Coming in at a solid 4.0-star rating from 24 reviews, this approximately 2.5-hour private tour offers a more intimate look at Montepulciano’s underground world. Starting from Piazza Grande, this guided walk takes you into two of the town’s most famous vaulted cellars, where you will see gigantic oak barrels used for aging the celebrated Vino Nobile di Montepulciano. The tunnels, carved into the tuff stone, have been part of local life for centuries, and this tour provides a detailed look into their history and significance. Your guide, Laura, is praised for her knowledge and engaging storytelling, making the history come alive.
This tour stands out because of its private setting, giving you personal attention and the chance to ask questions. It’s priced at $67.99 per person, offering good value for a small-group experience. Visitors consistently mention the quality of the explanations and the opportunity to see the cellars up close — a rare glimpse into the town’s wine heritage. The tasting of both Rosso di Montepulciano DOC and Vino Nobile DOCG caps the visit on a high note. If you’re after a more personal experience with expert guidance, this tour is a smart pick.
Bottom Line: Perfect for those seeking an exclusive, guided exploration of Montepulciano’s underground cellars and history, with a focus on quality and personal attention.
How to Choose Between These Tours
When deciding which Montepulciano cellar tour fits your style, consider your priorities. The first option (Montepulciano: Historical Cellars Guided Tour & Wine Tasting) offers a longer, group-oriented experience with a focus on storytelling and a broader overview of the town’s wine culture. It’s great if you want to learn in a lively setting and enjoy tasting multiple wines.
The second option (Tour of the historical cellars in Montepulciano) caters to travelers who prefer a more private, personalized experience. If you value intimacy and detailed explanations from an expert guide, this private tour is the way to go, especially since reviews highlight Laura’s detailed knowledge.
Consider your budget, time available, and whether you prefer a small group or a more social atmosphere. Booking early is advisable, especially during peak seasons, to secure your preferred date and guide.
Final Thoughts
Both tours offer exceptional insights into Montepulciano’s wine cellars and history, but they cater to slightly different preferences. The guided group tour is perfect for those who enjoy a lively atmosphere and want to sample a variety of wines along the way. Meanwhile, the private cellar tour appeals to travelers seeking a more intimate, detailed experience.
If you’re a wine enthusiast eager to understand the roots of Montepulciano’s famous vintages, either choice will serve you well. For those with limited time, the 2-hour experience still packs a punch, giving you a meaningful taste of the town’s rich winemaking heritage. Remember to book early, especially in high season, to ensure you don’t miss out on these memorable tours.
No matter which tour you pick, you’ll walk away with more than just wine — you’ll have a deeper appreciation for Montepulciano’s history and its legendary wines.


