Siena: Underground Wine Tasting in Private Medieval Cave

Summary

Private Siena wine tasting inside ancient Etruscan cave with sommelier

You’ll step through an unmarked door near San Domenico into Siena’s oldest underworld for a private wine tasting led by a local sommelier. Taste Brunello di Montalcino, Chianti Classico, and Super Tuscan wines inside an Etruscan-era cave with only a handful of guests. Expect stories, laughter over local cheese, and that rare feeling of being let in on something secret.

What’s the experience like?

We were already halfway down the narrow stone steps when I caught that first earthy chill — you know, that damp smell of old stone and something older. Our guide, Francesca, flicked on a little flashlight and grinned back at us. “This is the real Siena,” she said, her voice echoing just enough to make me shiver (in a good way). I’d read about medieval caves before but standing there, actually touching the rough wall, it hit different. There’s no sign outside — just this quiet door near San Domenico. I almost missed it.

Inside, the air was cool and heavy with something like wet clay and faint red wine. The table was set simply — pecorino cheese, some bread, nothing fancy. Francesca poured our first glass (a Chianti Classico) and started telling stories about Siena’s old rivalries and how these caves used to hide more than just bottles. She knew her stuff but didn’t make it feel like a lecture — more like chatting with someone who really loves this place. At one point I tried to pronounce “Brunello di Montalcino” right and she laughed — apparently my accent is hopeless.

I still think about the way the candlelight hit those dusty bottles lined up along the wall. We tasted three wines in total — including a Super Tuscan that made me pause longer than I expected (I’m not usually dramatic about wine). Between sips, Francesca gave us tips on where locals actually eat in Siena (“skip the main square if you want real pici pasta,” she whispered). There were only six of us down there so it felt private in that way you can’t fake. The tour finished before I was ready for daylight again — weird how fast time moves underground.

Step-by-step itinerary

Day 1 — Wine tasting in medieval cave

• View city and Basilica near San Domenico
• Arrive at underground medieval cave
• Taste selection of local wines
• Learn about Siena history from guide

Top questions

How many people are allowed on this Siena wine tasting tour?

The experience is limited to 12 people per day due to its private setting.

Is the underground wine tasting accessible by public transport?

Yes, public transportation options are available nearby in Siena.

Are service animals allowed during the tour?

Yes, service animals are allowed on this wine tasting experience.

Which wines are included in the tasting?

You’ll taste Brunello di Montalcino, Chianti Classico, and Super Tuscan wines from Siena’s region.

Is food included during the Siena underground wine tasting?

Pecorino cheese is served alongside the wines during your tasting.

Is this tour suitable for pregnant travelers?

No, it’s not recommended for pregnant travelers.

What is the minimum drinking age for this experience?

The minimum drinking age required is 18 years old and above.

Does the tour run rain or shine?

Yes, this Siena underground wine tour operates rain or shine.

What’s included

Your day includes exclusive access to a private medieval cave beneath Siena near San Domenico, guided by a certified sommelier who leads you through tastings of Brunello di Montalcino, Chianti Classico, and Super Tuscan wines paired with local pecorino cheese—plus personal tips on where to eat around town before you head back above ground.