Siena is an excellent base if you’d like to explore the iconic Chianti wine region. The city is compact, has plenty of hotels, and is an ideal starting point for wine tastings in Tuscany. Due to its proximity to numerous estates, you will easily immerse yourself in the century-long tradition of Italian winemaking. Moreover, you’ll also visit Tuscany’s highlights through the best wine tours from Siena: from picturesque villages to breathtaking landscapes, everything will unroll out of your window.
Therefore, in this article, I handpicked several Chianti wine tours from Siena, together with descriptions and prices. Since I visited the region on an extensive Tuscany road trip, I preferred to split the article into two sections. In the first section, you’ll discover dedicated tours focusing exclusively on wine. On the other hand, if you are more interested in exploring this side of Tuscany and just sipping a glass of wine, the second section will be closer to your interests.
So, let’s start with the best Chianti wine tours from Siena, Italy, and see what you can expect from them.
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The best wine tours from Siena for wine lovers
As I already wrote, in this section, you will find wine tours dealing exclusively with visits to wineries. While you’ll see the Tuscan landscape unfolding out of the window, the goal here is to taste as much local wine as possible. There’s not that much exploration of towns or villages, and everything is about Chianti wine. However, the experience is rewarding, and you’ll get a great overview of the grapes and wines of the area.
Wine tour in Chianti
This is one of the most affordable Tuscany wine tours from Siena; therefore, if you’re on a tight budget, make sure to check it out. However, please keep in mind that transfer is not included in this tour. That said, you’ll have to visit the winery on your own.
So, this Chianti wine tour from Siena will let you explore a small, family-run organic winery. You’ll learn everything about organic winemaking, and you’ll taste Chianti Classico wines in the place they’re produced. Apart from learning the place’s history, you’ll have a walking tour through the vineyards, and you’ll visit the cellar. There, you can try all five wines of the estate accompanied by cheese and meat. And, of course, you can buy wine bottles at the tour’s end.
For people traveling to Tuscany on a budget, this is probably the best option for experiencing the region’s products and traditions up close.
Duration: 2 hours.
Price: from 39,99 euros.
How to book: Book here the Total Immersion in Chianti.
Romantic dinner in the Chianti Vineyards
That’s one of the most romantic wine tours from Siena you can book right now. Having a dinner with the Tuscan landscape on your feet is something unique, and this tour will bring you to a farm where you will initially participate in winetasting. Then, after a quick stop at the estate’s chapel, you’ll head for a candle-lit dinner under the stars.
The dinner consists of a four-course menu with traditional recipes from the area. You’ll taste pappa al Pomodoro or ribollita, meat, and seasonal organic vegetables. After enjoying several glasses of local wine and a dessert, you’ll return to Siena.
Duration: 4 hours.
Price: from 95 euros.
How to book: Book the Chianti dinner here.
Brunello di Montalcino wine tour
This Brunello wine tour from Siena will take you to the iconic town of Montalcino. Montalcino is one of the most beautiful places in Tuscany and is home to famous wineries. A minivan will pick you up from your accommodation in Siena and drive you back after the tour ends.
The Brunello di Montalcino is a world-famous wine. On this tour, you’ll stop in two wineries where you can try the Brunello, learn about its history, and explore the facilities of the wine estates. I find the price reasonable, especially if you consider what this wine tour offers and also its duration.
On a side note, I must admit that the Brunello di Montalcino was my favorite wine when I visited Tuscany.
Duration: 5,5 hours.
Price: from 119 euros per person.
How to book: Book the Brunello di Montalcino tour here.
Educational tour and wine tasting in Siena
If your journey’s goal is to learn everything about Italian wine, here’s an excellent guided tour for you. The Educational Wine Tour takes place on a farm in Siena, so it’s straightforward to reach. A wine expert will guide you through the wine cycle and explain the vineyard’s complexity and procedures to you. That’s a very rewarding tour if you’d like to learn everything about Chianti wine while tasting it.
Afterward, you’ll uncover the secrets of the cellar and learn about all the processes that take place there. A deeper understanding of the Chianti winemaking tradition is at the core of this tour and feels like a journey to flavors and tastes. Of course, after this wine masterclass, you’ll enjoy delicious food accompanied by wine.
Duration: 3 hours.
Price: from 85 euros.
How to book: Book the educational tour here.
The best Chianti wine tours from Siena for explorers
The second section of this wine tour guide is for people who prefer exploring the towns and villages of the Chianti region. While visiting a winery or a wine estate is included in every trip in this section, the focus is mainly on the places. After visiting one or more towns/villages, you’ll also stop at a winery for a glass (or two) of high-quality Chianti wine. However, these day trips mainly explore the region, and wine drinking is a nice plus.
These day trips are ideal for first-time visitors to Tuscany because they include visits to famous locations, background information, unbeatable countryside images, and, of course, Chianti wine tastings.
Chianti and Castle tour by minivan
This half-day trip will drive you through parts of the Tuscan landscape. The wine tour starts from Siena and brings you to two wineries. There’s a strong focus on high-quality wine tasting, and you’ll learn about the local grape varieties: Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon. On your way, you’ll also stop at ancient churches and castles, where you can discover how life unfolded in the region.
This is a small group tour, and the minivan can accommodate up to 8 people. Therefore, book your place in advance to secure your seat(s).
Duration: 5 hours.
Price: from 85 euros per person.
How to book: Book here the Chianti and Castle tour.
Brunello di Montalcino full-day tour
This day trip starts from Siena, and it’s a perfect option if you’d like to spend time in nature. However, please note that the organizer won’t pick you up from your Siena hotel. Instead, you’ll have to meet them at a designated point in Siena. The city is compact, and this won’t be a problem; however, keep in mind that you should arrive on time for the tour.
Since this is a day trip, part of the experience is all about the stunning landscape of Tuscany. The guide will drive you through the ancient Siena-Montalcino road, and your first stop will be at a local winery. There, you’ll taste the renowned Brunello di Montalcino. Afterward, you’ll visit the beautiful hill town of Montalcino, where you can explore its fortress and walk around it. If you’re up for some more wine, you can taste it at local wine bars.
The day trip will then take you to the Benedictine Abbey of Sant’Antimo, where you’ll have lunch at a family-run winery. Finally, late in the afternoon, a third winery awaits you. In this final stop of the tour, you’ll learn about the aging process in oak barrels, and you’ll taste the wines before heading back to Siena.
Duration: 9 hours.
Price: from 180 euros per person.
How to book: Book the full-day tour to Montalcino here.
Pienza, Montalcino, and Montepulciano wine tour from Siena
This day trip is somewhat similar to the above tour but even more extended in duration. It will take you to three Tuscan gems. I mainly add this tour here because you’ll be able to see one of the most stunning locations of the Renaissance: Pienza. I wrote extensively about it in my Pienza travel guide, so check it out if you decide to take this awesome wine tour.
So, this is one of the finest wine tours from Siena, and it’s available in several languages. Make sure to choose yours during the booking process. The tour departs from a meeting point in Siena, and you’ll visit first Montalcino, where you’ll taste local wines. Then, you continue to Pienza, the jewel of Tuscany located in the Val d’Orcia. Finally, the tour finishes at Montepulciano, where you’ll also enjoy a Chianti wine tasting.
In my opinion, that’s the best wine tour in Siena because it combines three of the most famous winemaking locations in Chianti. Seeing, understanding, and enjoying local wine at a slow pace will offer you a memorable experience.
Duration: ~11 hours.
Price: from 95 euros per person.
How to book: Book the Montalcino, Pienza, and Montepulciano tour here.
San Gimignano, Montalcino & Wine Tasting
That’s one more excellent wine tour from Siena. You will visit the medieval town of San Gimignano, one of the most iconic locations in Tuscany. The city is famous for its towers: people often refer to it as Medieval Manhattan. A UNESCO World Heritage Site, San Gimignano is a must-see on your trip. If you’d like to learn more about the medieval city, you can also read my San Gimignano travel guide here.
On this tour, you’ll have plenty of time to explore Italy’s world-famous medieval town. San Gimignano is known for the Vernaccia, a white wine produced only in this area. Then, you’ll head over to Monteriggioni, an ancient fortress mentioned in Dante’s Inferno. There, you’ll also visit a winery where you’ll have lunch and taste Chianti wines. Finally, you’ll visit Montalcino, where you can also taste local products and Brunello wine.
If you’re on a tight schedule, this tour is a great option for visiting both San Gimignano and Montalcino. Both places are must-sees, and visiting them on one trip is fantastic.
Duration: ~11 hours.
Price: from 140 euros.
How to book: Book the San Gimignano & Montalcino tour here.
Vespa & Chianti tour in the Tuscan hills
I doubt it gets more Italian than this. This wine tour from Siena will let you spend time driving a Vespa on the picturesque roads of Tuscany. You’ll visit numerous small villages in the Tuscan countryside, and you’ll stop on a famous farm for a Chianti wine tasting paired with a delicious lunch.
If you don’t feel comfortable driving a Vespa, don’t worry: you can ride with one of the guides. It’s a truly unique experience in the marvelous Italian landscapes.
Duration: 7,5 hours.
Price: 129 euros.
How to book: Book the Vespa & Chianti here.
Bonus: You can book a similar tour with a Fiat 500 instead of a Vespa. Everything is identical on this tour, but instead of a Vespa, you’ll drive an old-fashioned Fiat 500. Apparently, if you’re not up for driving yourself, one of the tour guides will drive the car, and you can just enjoy the region’s beauty.
The best wine tours from Siena: Final Thoughts
While Florence is the absolute highlight of the region, Siena enjoys a strategic location in Tuscany. Some of the best Chianti wineries are close to the city, and the Siena wines are among the best you can drink in Italy. Every Tuscany wine tour from Siena will expose you to the region’s beauty and will let you immerse yourself in local tastes and aromas. Exploring a region while sipping a glass of local wine is one of the nicest things to do while traveling.
Moreover, most wine tours from Siena to Chianti follow different paths, and if you decide on various wine tastings, you’ll have an even better impression of the area. Seeing iconic towns and enjoying the area’s famous wines is a must-do experience if you’re visiting Italy’s most beautiful region.
So, that’s it with the Chianti wine tours in Siena and the best wineries near the city. Let me know in the comments if you plan to visit Siena, Italy, and if you have already booked a wine tour.
More about Italy: Where to stay in Siena with a car, Piazza del Campo facts, Arezzo, San Marino, Florence Facts
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Last Updated on August 13, 2024 by George Pavlopoulos