Beneath Siena's streets lies a second city: cellars, tunnels and cisterns, some of them part of the medieval water system known as the Bottini. This experience takes you underground for a wine tasting in a medieval cave, which is a memorable way to taste Tuscan wine in a setting that is cool in summer and calm in winter. The tasting is rated a perfect 5.0 by guests, with more than sixty reviews. A host introduces a few wines from the region, usually including Chianti Classico and other local reds, explains how to taste them, and serves them with a few simple local products. The cave adds atmosphere that a bar cannot match, with stone vaults, soft lighting and a sense of history. The session is short enough to fit between sightseeing and dinner, and it is a good choice for couples and small groups.
The setting
Siena grew on three ridges with no river, so for centuries the city relied on an underground network of tunnels that collected spring water and carried it to the fountains. This network, the Bottini, runs for kilometres under the old town, and many of the cellars and vaults beside it have been used for storage and, today, for tastings.
The cave used in this experience is described as a medieval cave, and the tasting takes place in its stone chamber. The air underground is cool and steady, which is why wine and food were stored there. If you are sensitive to cold or to enclosed spaces, bring a light layer and tell the host.
The tasting
You can expect a small flight of wines, introduced one at a time with notes on the grapes, the producers and the places they come from. The Sangiovese grape is the backbone of Chianti, Brunello and Vino Nobile, and tasting several wines side by side is an easy way to hear the differences.
The wines are usually paired with a few bites of local products such as cheese, cured meats, bread and olive oil, but check the details when you book, because the exact selection varies. The talk is relaxed and aimed at curious beginners as well as people who already know their wine.
Who it suits
Couples, friends and small groups who want a short, atmospheric activity that does not demand a day trip. It also suits travellers who like wine but do not want to drive, since the tasting takes place in the city and you can walk back to most hotels. Children are not usually part of a wine tasting, so check the age policy. Because access may involve steps and uneven stone, it may not suit people with limited mobility, and you should ask the operator before booking.
Planning
Sessions are scheduled at set times, often in the afternoon or early evening, and groups are small. Book ahead for weekends and holidays, and arrive on time, since the tasting begins together. Pair the session with a visit to Piazza del Campo and the Fonte Gaia, which is the fountain that the Bottini fed, so you can see both ends of the water system in a single afternoon.
For a longer wine experience, add a Chianti day trip, where you taste at the estates where the wines are made. Read cancellation terms when you book, as they depend on the date.
What to expect
The experience
A guided tasting of several Tuscan wines with local bites in a medieval cave beneath Siena, led by a host who explains the wines.
Best time
Late afternoon or early evening, as a break between sightseeing and dinner.
How long
Allow about ninety minutes for the tasting, plus time to reach the meeting point.
Tips
Bring a light layer for the cool air, wear shoes for uneven stone, tell the host about allergies and arrive on time.
Quick picks
- Best for
- Wine lovers and curious visitors who want an atmospheric tasting in the city itself.
- Families
- A wine tasting is for adults, so check the age policy before bringing children.
- Couples
- A candlelit-feeling cave and a glass of Tuscan red make an easy and romantic start to the evening.
- Pair with
- Piazza del Campo and the Fonte Gaia, a food tour or dinner in the old town.
- Time needed
- An hour and a half.
Good questions
Where does the tasting take place?+
In a medieval cave under Siena's old town. You will get the exact meeting point when you book.
Which wines will I taste?+
Tuscan wines are typical, often including Chianti Classico and other local reds. The exact selection varies, so check the booking details.
Is food included?+
Local bites such as cheese, cured meats and bread are usually served with the wine. Confirm what is included when you book.
Is it suitable for people with limited mobility?+
Access to underground spaces can involve steps and uneven stone, so ask the operator before booking.
Is it cold underground?+
The air in caves stays cool all year, so bring a light layer, particularly in summer when the contrast with the street is greatest.







