More about: 9 Best Wine Tours in Siena
Siena is located in the region of Tuscany, Italy, famous for its delicious wines and historic beauty. Among the best things to do in Siena, taking a wine tour is an excellent way to get to know the region and delight in some of the most renowned Italian wines. There are options for all tastes, from walking tours to Vespa or horseback tours, which will take you through the vineyards and wineries.
Its red wines are elegant and complex, and with this type of tour you can taste some of its best vintages, as well as learn more about the production process. It's true that when there are so many options it can be difficult to know where to start, which is why I have selected the most outstanding wine tours in Siena. Keep reading, you won't regret it.
1. Wine tour with tasting in Siena

Take a relaxing tour of an organic vineyard in Tuscany, just 2 km from the historic centre of Siena. You'll learn about the wine-making process, the grapes and their agronomic cycle. This is a unique experience, where you can witness every step of the process, from the vineyard to the glass.
This is undoubtedly one of the best tours in Siena. It will allow you to discover one of the region's most distinctive features in detail, as its wines are famous throughout the world. Afterwards, you will enjoy a tasting of four different varieties of wine, all typical of Tuscany.
In addition to the tasting in the winery, a light lunch with local seasonal products is included, where you can be sure that delicious extra virgin olive oil from Siena will not be missing. An unmissable tour for lovers of flavour.
Details of interest
- Price: from £76 per person.
- Duration: approximately 3 hours in total.
- Transport: transport to the venue is not included.
2. Vespa tour of Siena with lunch at a Chianti winery

Experience a different kind of adventure. Hop on a classic Italian Vespa and ride through the roads of Tuscany, enjoying lunch and wine tasting at a local winery. While there are many wine tours in Siena and the surrounding area, this one is unique in that you can drive yourself through the green Italian countryside and follow your guide for a complete experience.
Of course, if you don't feel like driving, your guide can also take you. You'll get to know the region in the most typically Italian way and enjoy the Chianti Valley and Monteriggioni with its medieval castles. Then you'll stop along the way to enjoy lunch and a tasting of locally made wines. Considered one of the 10 best food tours in Siena, this experience is unbeatable.
One detail to keep in mind is that this tour includes a guide in English, so if you don't speak Italian, don't worry, you won't miss a thing.
Details of interest
- Price: from £126 per person.
- Duration: approximately 7 hours and 30 minutes in total.
- Transport: you will tour Siena on a classic Italian Vespa motorbike.
3. Tour with dinner in the vineyards of Siena

On this tour, you will have the opportunity to enjoy an authentic Italian dinner in an incomparable setting. You will be taken in a comfortable minivan to an estate in Tuscany, more precisely in the Chianti Valley region. There you will visit the vineyards and wineries where one of the world's most famous wines is produced.
After a walk along the beautiful paths and plantations, and as the sun sets, you will enjoy a delicious traditional Italian dinner. You will savour dishes made with fresh seasonal produce, paired with the most delicious wines of Tuscany. This is undoubtedly one of the best things to do in Siena at night.
It is a unique experience, as wine tours are usually held during the day. You will be able to taste some of the Chianti wine varieties and enjoy an exceptional atmosphere under the stars. In addition, your guide will tell you everything you need to know about Tuscany and its delicious wines.
Details of interest
- Price: from £89 per person.
- Duration: approximately 5 hours in total.
- Transport: you will be driven in a comfortable minivan.
4. Classic Tuscan wine tour

Immerse yourself in the world of Tuscan wine and learn everything you need to know to fully enjoy one of the most renowned wines in the world. Tuscany is famous for being a region with centuries of history, medieval castles, stone streets and dreamlike landscapes. But without a doubt, one of its main attractions and one of the reasons why it welcomes so many visitors every year is its wine.
At this school, located in the centre of Siena, you will learn the secrets of good wine tasting, what to look for, its texture, body and colour. Put yourself in the hands of professionals and become an expert in Tuscan wines.
Details of interest
- Price: from £60 per person.
- Duration: approximately 2 hours in total.
- Transport: the school is located in the centre of Siena, transport is not included.
5. Walking tour of Siena with food and Chianti wine

This option will take you on a tour of the historic centre of Siena with a local guide. You will learn all the secrets and stories of this incredible place, stroll through Piazza del Campo, which has been declared a UNESCO World Heritage Site. You will see all the charm of its monuments and taste the best of Tuscan cuisine, accompanied by Chianti wine.
This tour is not your typical excursion, as it takes you to places and meeting points frequented by locals, where you can taste Pecorino cheese, Tuscan prosciutto, traditional finocchiona salami and artisan bread, finishing with some delicious Ricciarelli, the typical sweets of Siena.
If you are in Siena for just a few days, this tour is ideal for getting a taste of the local flavours and history. Definitely one of the best tours to do in Siena in 2 days, you won't regret it.
Details of interest
- Price: from £49 per person.
- Duration: approximately 2 hours in total.
- Transport: walking tour through the centre of Siena.
6. Tour with wine tasting in a medieval cave in the heart of Siena

What could be better than enjoying a tasting of Tuscan wines in a place steeped in history? This experience will take you to the hidden heart of Siena, through its underground tunnels, to a stone cave located very close to Siena Cathedral, which dates back to the year 600.
The tour begins at the Basilica Cateriniana San Domenico, where you can enjoy excellent views of the city. Next to it, you will visit Piazza San Domenico, before descending through stone passageways to the tasting site. Here you will have the opportunity to taste some of the most renowned local wines, such as Chianti Classico, Super Tuscans and Brunello di Montalcino.
Details of interest
- Price: from £55 per person.
- Duration: approximately 1 hour and 15 minutes in total.
- Transportation: the tour is on foot.
7. Wine tasting and typical Tuscan products on a panoramic terrace

Visit the beautiful San Giorgio a Lapi vineyard and winery, where you can sit on a beautiful panoramic terrace located just 6 km from the centre of Siena, more precisely on the border between Chianti Colli Senesi and Chianti Classico. From there, you can admire the Church of San Giorgino and the white mulberry tree while tasting three glasses of the most delicious homemade wine.
In a pleasant and relaxed atmosphere, the owners will tell you everything about the cultivation and production of both wine and extra virgin olive oil. You can also enjoy a brunch with local products in an absolutely majestic natural setting.
Details of interest
- Price: from £25 per person.
- Duration: approximately 1 hour and 30 minutes in total.
- Transport: does not include pick-up or return to the hotel.
8. Horseback riding tour with wine tasting in Siena

Experience all the charm of Tuscany in a completely different way. On this tour, you will see the rows of vineyards and olive groves around Siena on horseback. Your guide will take you to explore the fields and hills of one of the most beautiful regions in Italy.
You will visit the winery and learn about the wine-making process, from the vine to the bottle. Afterwards, you will visit an organic farm, where you can enjoy an authentic Tuscan lunch and a tasting of their best wines, as well as their extra virgin olive oil.
An excellent way to get in tune with nature and learn more about Tuscany and its incredible wines.
Details of interest
- Price: from £280 per person.
- Duration: approximately 5 hours in total.
- Transport: you will go on a horseback ride.
9. Self-guided walk and wine tasting in Siena

Take a walk through the charming medieval streets of Siena and finish by tasting the most incredible Tuscan wines in a local winery. The tour is self-guided, meaning that you will receive all the instructions on your mobile phone to take a tour of the best of Siena.
Sometimes, these types of tours allow you to go at your own pace and not have to deal with other travellers. You'll visit the most interesting corners of the city until you reach the winery, where an exclusive tasting of Tuscan wines and a typical regional lunch await you. It's a family-run winery, so you'll feel right at home.
Details of interest
- Price: from £102 per person.
- Duration: approximately 8 hours in total.
- Transport: you will explore the city on foot.
How to book a wine tour in Siena

As I always say, the best way to book an excursion is online, so you can see what other users think about the excursion. Plus, you can pay online from the comfort of your mobile phone or computer.
Duration of a wine tour in Siena

The duration ranges from just over 1 hour to 8 hours. It will always depend on the type of excursion you prefer. Don't forget that if you are travelling with young children, a tour that is too long is not recommended.
What will I see on this type of excursion?

These tours focus on experiences related to the world of wine in Tuscany. You can choose between wine tastings and walks around the city and its surroundings, or authentic traditional meals with tastings of different local wines.
Tips for a wine tour in Siena

Keep in mind that if the tour you have chosen does not include any meals, it is best not to go on an empty stomach, as you may feel sick or dizzy.