Best Wine Tours in Siena, Italy: Picked by a Tuscan Wine Enthusiast

This is a list of 10 wine tours bookable from Siena – covering half-day and full-day options, from intimate small-group visits to Brunello and Chianti Classico wineries, to in-city wine classes and a rather special underground tasting in an Etruscan cave.

I’ve made several trips to the Siena wine region and have spent time in Montalcino, Montepulciano and the Chianti estates – staying in each area, visiting wineries, and drinking more Brunello, Vino Nobile and Chianti Classico than is probably sensible. 

I also regularly buy and drink wines from the region at home. 

Brunello di Montalcino is mine and my partner’s wine of choice for special occasions – which tells you everything you need to know about where I stand on it. Vino Nobile is the one most people underestimate. Chianti Classico, done well, is the one you end up drinking most of over the course of a week in the region.

The 10 tours below are organised by type. The tips section at the end covers what to actually look for when choosing between them.

3 Top Picks at a Glance

Top Pick: Small-Group Brunello di Montalcino Wine-Tasting Trip

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Duration: 9 hours

Selling points: Unique visits to 3 distinct wineries + traditional Tuscan lunch

Book this Tour

Second Pick: Educational Wine Tour & Tasting at La Lastra

Educational Wine Tour & Tasting

Duration: 3 hours

Selling points: In-depth exploration of organic winemaking + sensorial tastings

Book this Tour

Third Pick: Wine Class – Tuscan Classics

Wine Class – Tuscan Classics

Duration: 2 hours

Selling points: Interactive Tuscan wine education in Siena’s historic heart

Book this Tour

10 Wine Tours from Siena: Quick Comparison

10 Wine Tours from Siena

1. Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

★ RATING: 5/5 Stars | 🕰 TOUR LENGTH: 9 hours | ✓ Book now

This is my top pick and it isn’t particularly close. 

I chose it because the structure is exactly right for anyone who takes Brunello seriously – three distinct wineries in a single day means you actually start to understand the variation between estates, rather than forming an opinion based on one tasting. 

The small group size of eight is important too; I’ve been on wine tours where you’re processed through a cellar with twenty other people and it strips all the atmosphere out of it. This one doesn’t do that. 

The traditional Tuscan lunch at a family winery is included, and the tour also takes in Montalcino village and the Sant’Antimo Abbey. Over 600 five-star reviews backs up what the itinerary already suggests. 

I’d recommend this to anyone who has drunk Brunello before and wants to understand it better – and equally to anyone who hasn’t yet but wants to start properly.

Reviews:

“Highly highly recommended. Mattia was so knowledgeable and full of fun stories. The wineries that we visited were all very unique. The lunch! The location was fabulous. The hosts were even more fabulous and their wines amazing.” – Nancy_C

Read more reviews here.

2. Educational Wine Tour & Tasting

★ RATING: 4.9/5 Stars | 🕰 TOUR LENGTH: 3 hours | ✓ Book now

I picked this one because it’s the most genuinely educational option on the list, and because the location – 2km from the centre of Siena – makes it accessible without needing a full day or a driver. 

La Lastra is an organic winery, and the tour walks you through the full agronomic cycle from vineyard to cellar before sitting down to taste four organic wines. 

What I liked about the format is that it’s structured around understanding rather than just consuming – you leave knowing something about how the wine was made, which changes how you taste it. 

A light seasonal lunch is included and the group is capped at 12. 

I’d point this one at people who are curious about the winemaking process and want more than a standard tasting, but don’t want to lose a whole day to it.

Reviews:

“The wine tour and tasting at La Lastra was excellent. Our host spoke very informatively and passionately about their ‘terroir’. I’ve done a few wine tours over the years and expected this to be just another experience- but I genuinely learned a lot during our visit. The lunch and tastings provided were generous and delicious. Thank you so much – 5* – don’t miss it!” – GetYourGuide traveller, United Kingdom

Read more reviews here.

3. Wine Class – Tuscan Classics

★ RATING: 5/5 Stars | 🕰 TOUR LENGTH: 2 hours | ✓ Book now

I included this one specifically for people who are earlier in their Tuscan wine journey, or who want a convivial evening in Siena without committing to a full day out in the countryside. 

It’s a two-hour in-city class in the historic centre, tasting four to five Tuscan wines with food pairings, led by English-speaking local experts. 

The 5pm start makes it a natural aperitivo-hour activity – you’re essentially spending your evening learning to drink Tuscan wine properly, which is a very good way to spend an evening in Siena. 

I’d recommend it to anyone who wants to be able to hold their own in a Tuscan enoteca by the end of the trip, and to couples who want something structured and social rather than another restaurant dinner.

Reviews:

“Terrific class. Had a ton of fun. So convenient being in the city walls. Drank, laughed and learned a great deal. Manuel was a terrific teacher and good-natured person. No pressure sale. If you don’t know much about wine from Tuscany, want to learn and drink with a friendly group, this tour is for you.” – Hanan_S, May 2023

Read more reviews here.

4. Chianti and Castles Tour with Wine Tastings

★ RATING: 4.5/5 Stars | 🕰 TOUR LENGTH: 5 hours | ✓ Book now

I chose this for people who want to actually see the Chianti countryside rather than just taste the wine in a city setting – which matters, because the landscape is a huge part of why Chianti Classico tastes the way it does. 

It’s a five-hour half-day by minivan, taking in two wineries and the medieval town of Castellina in Chianti, with an olive oil tasting along the way. The group is capped at eight, which keeps it from feeling like a coach tour. 

I’d point this one at anyone based in Siena who has a half-day free and wants to get into the hills – it’s not a deep dive into any single estate, but it gives you a real feel for the region in a manageable format.

Reviews:

“Marvelous! The guide was very nice. He knew everything very well, he was able to explain everything. The wines were one better than another and the people from the vineyards have also given us special treatment! I recommend 100%, we have had a phenomenal day, I will never forget it.” – Gustavo, Spain

Read more reviews here.

5. Val D’Orcia Wine Tour

★ RATING: 4.1/5 Stars | 🕰 TOUR LENGTH: 8.5 – 10 hours | ✓ Book now

I included this primarily for travellers who don’t have a car. 

It’s the most logical solution if you want to reach Montepulciano, Pienza and the Val d’Orcia without driving yourself, and it handles all the logistics – air-conditioned minivan, multilingual guide, wine tastings and snacks at a cellar stop. 

The day runs eight and a half to ten hours, which is long, and the trade-off is that time at each location is limited. 

I’d be honest that if you do have a car, you’ll get more out of the Val d’Orcia by going independently and staying longer – but if you don’t, this is a well-organised way to see one of the most beautiful parts of Tuscany without the stress of navigating it yourself. 

Read recent reviews to check the current pace before booking.

Reviews:

“This is a great option for those without a car! This small group tour first stops at a winery, where you get to go down into the cellar cave to try multiple red wines. You then stop at two different picturesque towns and get time to explore on your own. Before you each stop, our guide gave us the history of the town and recommendations of what to see and do. The ride itself was very comfortable in a new luxury van.” – GetYourGuide traveller, United States

Read more reviews here.

6. San Gimignano, Montalcino & Wine Tasting

★ RATING: 4.6/5 Stars | 🕰 TOUR LENGTH: 11 hours | ✓ Book now

I picked this one for the sheer breadth of what it covers in a single day. 

Eleven hours is a genuine commitment, but the itinerary earns it: San Gimignano including a Vernaccia tasting, a drive through the Val d’Orcia, Montalcino and a Brunello tasting, plus lunch with Chianti at a winery en route. 

Group size is capped at eight with a bilingual guide throughout. 

I’d recommend this specifically to first-time visitors to the region who want to orient themselves across the different wine zones before deciding where to spend more time on a future trip – or to people who only have one day for the countryside and want to make it count. 

Go in knowing you’re getting a flavour of each place rather than a deep exploration of any one of them.

Reviews:

“An absolutely magical experience! My husband and I had a fantastic day and felt like we were in a film, sipping delicious wine with the backdrop of the beautiful Tuscan countryside. It was a good balance of wine tasting, eating and drinking and exploring. Our guide (Vincenzo, I think!) also gave a commentary about what we could see, while we were driving between destinations. It was expensive, but totally worth it. :)” – Lauren, United Kingdom

Read more reviews here.

7. Siena Underground Wine Tasting in a Medieval Cave

★ RATING: 5/5 Stars | 🕰 TOUR LENGTH: 1 hour 15 minutes | ✓ Book now

I chose this one because it’s unlike anything else on this list – or, honestly, on most wine tour lists. 

It’s a 75-minute tasting hosted by a sommelier in a medieval cave beneath the streets of Siena, dating to the Etruscan period around 600 BC, and it’s the only space of its kind accessible to the public in the city. 

I’m drawn to wine experiences that are rooted in place, and this one couldn’t be more rooted – you’re drinking Brunello di Montalcino, which regularly appears in Wine Spectator’s top 100, in a cave that’s been here for over two and a half thousand years. Local cheese and snacks are paired with the wines. 

It’s limited to 13 people per day, so you need to book ahead. I’d recommend it to anyone with a genuine interest in wine and Sienese history – and equally to anyone who just wants the most memorable hour and a quarter they’ll spend on the trip.

Reviews:

“Outstanding local tour leading to a wine store fully packed with all kinds Italian wines! Owner is knowledgeable and tells a great history. You should go!” – Carolyn_F, Apr 2023

Read more reviews here.

8. Vespa Tour with Lunch & Chianti Winery from Siena

★ RATING: 4.5/5 Stars | 🕰 TOUR LENGTH: 7 hours 30 minutes | ✓ Book now

I included this one because it approaches the Chianti countryside in the way I think it deserves – from the saddle of a Vespa rather than the back seat of a minivan. 

Seven and a half hours through the hills, stopping at Monteriggioni and several villages along the route before finishing with lunch and a tasting of Chianti Classico and Super Tuscan at Casale dello Sparviero winery. 

Previous scooter experience is required, and it’s not for everyone – but if it suits you, it’s the most immersive and enjoyable way on this list to spend a day in the Chianti landscape. 

I’d recommend it to couples or small groups who want an adventure with good wine at the end of it, rather than a structured tour with a clipboard.

Reviews:

“A bucket list item to check off! What an excellent way to see Chianti on a Vespa! Fredricho was an excellent guide leading us and stopping at 3 towns allowing plenty of time to sightsee, shop, and experience the local atmosphere. Stopping at Casale Dello Sparviero Winery was amazing! Jada was an inviting and knowledgeable host and the light lunch and tasting was perfect!” – Jeffrey_J, Oct 2023

Read more reviews here.

9. Dinner & Drinks in the Chianti Vineyards

★ RATING: 4/5 Stars | 🕰 TOUR LENGTH: 4 – 4.5 hours | ✓ Book now

I chose this one as the best evening option on the list, and because I think the aperitivo-at-sunset-in-a-Chianti-vineyard format is one of those experiences that sounds like a cliché until you’re actually doing it. 

It’s four to four and a half hours at a traditional Tuscan farmhouse, starting with an aperitivo as the light drops and moving into a four-course dinner with estate wines. Runs June to September only. 

The group size goes up to 30, which is larger than I’d usually recommend, and reviews are genuinely mixed – some guests find it magical, others find it falls a little short. 

I’d say read recent reviews before booking, but if the recent ones are strong, don’t hesitate. It’s the kind of evening that becomes a highlight of a Tuscany trip when the conditions are right.

Reviews:

“Amazing, would really recommend this if you want good food, amazing wine and excellent staff who will teach you a lot about the wine and how to taste it. Thank you so much for the wonderful evening.” – Maaike, August 14, 2023

Read more reviews here.

10. Wine Tasting at the Winery in the Panoramic Terrace

★ RATING: 5/5 Stars | 🕰 TOUR LENGTH: 1 hour | ✓ Book now

I included this because it’s the most personal and understated option on the list, and because family-run estates with a genuine story tend to produce better wine experiences than the polished commercial ones. 

The Winery San Giorgio a Lapi is 6km from Siena, has been in the same family since 1977, with eight family members each responsible for a different part of the production. 

The tasting is held on a panoramic terrace overlooking the Sienese countryside and covers both wines and olive oil from the estate. 

One hour, private, available Monday to Saturday from 3-7pm. I’d point this at anyone staying in the area who wants a quiet afternoon rather than a structured group tour – or as an add-on to a Siena day for people who want to end it properly.

Reviews:

“What an amazing way to spend an afternoon. We had Mariana who looked after us and she was both very knowledgeable and enthusiastic. She taught us about the wines we were being served and the family history. The setting was sensational along with the wines we tried and the meat and cheese board we had.” – katienichurraoin, Sep 2023

Read more reviews here.

What to Keep in Mind When Choosing Siena Winery Tours

Choosing the right winery tour in Siena involves more than just a love for wine; it’s about the whole spectrum of experiences each tour offers. Based on my experiences, here are some considerations that might help guide your decision:

Reflect on your wine preferences and knowledge: It’s important to align the tour with your understanding and interest in wine. If you’re just beginning to explore the world of wines, an educational tour could be ideal. Conversely, for the aficionados, tours that delve into specific varieties, like Brunello di Montalcino offer a more sophisticated experience.

Consider the tour size: I’ve always found smaller group tours to be more intimate and enriching. They provide an opportunity for deeper interaction with the guide and a more personalised experience.

Look beyond the wine: Siena’s winery tours are not just about the wine; they’re about history, scenery, and culture too. Tours that integrate historical insights or local culinary experiences can enhance your enjoyment significantly if you enjoy these things, too.

Time and duration matter: Keep the tour’s length in mind. If your schedule is tight, opt for a shorter tour. However, if time allows, a full-day tour with vineyard walks and lunches can be a truly delightful indulgence.

Seasonality and weather: The Tuscan landscape changes with the seasons, affecting the wine tours. Some are seasonal, and others might offer a different experience depending on the time of year. Note that harvest happens around autumn and that vineyards mightn’t have as much time for visiting groups as at other times of the year. 

Accessibility and comfort: Make sure the tour fits your physical comfort and accessibility needs. Some tours may involve significant walking or may not be wheelchair accessible.

Wine Tasting in Siena: FAQ

What are the best wine-tasting tours in Siena?

From my explorations, the cream of the crop includes the ‘Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena‘ for its intimate and comprehensive exploration of Montalcino’s renowned wineries. ‘Educational Wine Tour & Tasting’ is a must for those interested in organic winemaking, and ‘Wine Class – Tuscan Classics’ offers a deep dive into Tuscan wines within the enchanting walls of Siena.

What wine is Siena known for?

Siena, nestled in Tuscany, is celebrated for its rich wine heritage. The region is particularly famous for its Chianti, known worldwide for its robust, versatile nature. Another gem is Brunello di Montalcino, a red wine esteemed for its depth and complexity (and a particular favourite of mine). 

Can you visit wineries on your own in Tuscany?

Yes, you can visit wineries on your own in Tuscany. Many wineries welcome walk-in visitors for tastings and tours. However, for a more structured and in-depth experience (and so you don’t have to worry about logistics or designated drivers), I recommend booking a guided tour. Some boutique wineries may require prior appointments, so it’s always a good idea to plan ahead.

What time of year is best for wine tours?

The best time for wine tours in Tuscany is from late spring to early fall (May to October). This period offers pleasant weather and the beautiful vista of vineyards in full bloom. Harvest season (September to October) is particularly magical, providing a unique insight into the winemaking process. Do remember, however, that wine makers will also be particularly busy, too, during harvest season!

What do you wear to a wine tasting in Tuscany?

When dressing for a wine tasting in Tuscany, comfort and practicality are key. Opt for smart casual attire. Comfortable shoes are a must, as you might walk through vineyards or stand for extended periods. Layers are advisable as temperatures can vary, especially if the tasting includes cellar tours. Remember, Tuscany’s wine country has an understated elegance, so while comfort is essential, a touch of style is always appreciated!

Before You Book: A Few Final Thoughts

The Brunello trip is the standout on this list for anyone who takes wine seriously – 600+ five-star reviews and a full day built around three wineries is a strong combination. 

If you’re short on time or prefer to stay in the city, the underground cave tasting is the most distinctive hour-and-a-quarter you’ll spend in Siena.

For everything else about Siena and the surrounding region:

• For how to spend your time in Siena itself: One Day in Siena: What to See & Do, from Someone Who’s Stayed Twice
• For wine tours across the wider Tuscany region: 15 Best Wine Tours in Tuscany

• For where to stay while you’re here: Best Airbnbs in Siena: Luxury, Historic & Characterful Stays