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The 15 Best Wine Tours in Siena
Siena is a treasure trove for wine lovers. Its location in Tuscany means access to some of Italy’s most renowned vineyards, and the city itself offers an authentic Tuscan backdrop for tasting Italy’s finest wines. Whether you're interested in premium Brunello di Montalcino, exploring small family-run wineries, or learning about Tuscan wines through a hands-on class, Siena's wine tour options are both varied and deeply engaging. One standout is the Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena, which combines expert guides, visits to three wineries, and a Tuscan feast, making it perfect for those wanting a comprehensive experience.
If you're short on time but eager to sample local wines and learn the basics, the Siena: A Wine Tour and Tasting Experience offers a compact, personalized introduction. For a more interactive approach, the Wine Class – Tuscan Classics helps you recognize regional reds and whites with local experts. With such options, Siena proves to be a superb base for exploring Tuscany’s vineyards.
Quick Overview
Our list of top Siena wine tours includes everything from luxury full-day trips to intimate tastings and educational classes. For those seeking a deep dive into Brunello di Montalcino, the Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch offers a full-day experience in some of the finest vineyards. Budget travelers will appreciate the Classic Wine Tasting and Typical Tuscan Products for its affordability and relaxed atmosphere. Looking for something more active? The Tuscany Hiking Tour from Siena Including Wine Tasting combines scenic walks with tasting stops. No matter your style, Siena has a wine tour that’s worth your while.
1. Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
This carefully curated day trip takes you to Montalcino — the birthplace of Brunello di Montalcino — with visits to three wineries, exploring vineyards, cellars, and enjoying a Tuscan meal paired with wine. The tour’s small-group format (with rave reviews like “personable and knowledgeable guides”) guarantees an intimate, relaxed experience. You’ll visit a family-run winery, tour the Abbey of Sant’Antimo, and learn the nuances of this exceptional wine.
What makes this tour stand out is the combination of education, local flavors, and authentic environments. Guests rave about the guides’ vinicultural expertise and the generous tastings at each stop. The included Tuscan lunch enhances the value, making it a full-day immersion that’s ideal for wine enthusiasts wanting a comprehensive look at Montalcino’s vineyards. Expect to taste both Rosso and Brunello di Montalcino, plus local delicacies.
Bottom line: A perfect choice if you want a small-group, deep-dive experience into one of Italy’s top wine regions, with expert guides and a delicious meal to round out your day.
2. Siena: A Wine Tour and Tasting Experience
For those pressed for time but eager for authentic Tuscan wine insights, this Siena wine tour offers a compact, personalized experience around the vineyards near Siena. Led by a knowledgeable sommelier, you’ll explore a historic cellar, learn how to identify subtle flavors, and sample at least four wines. The tour also includes a light Tuscan lunch, making it ideal for a cozy, educational afternoon.
This tour’s strength lies in its personalized attention and focus on educating your palate. Guests especially appreciate the detailed explanations of organic wine-making and the picturesque setting of Azienda Agricola La Lastra. At just around three hours, it’s tailored for those who want a quality taste of Tuscany without a full-day commitment.
Bottom line: A highly rated, intimate tasting perfect for beginners and seasoned wine lovers alike who want to learn and taste in a friendly setting.
3. Wine Class – Tuscan Classics
If you’re curious about the fundamentals of Tuscan wines, this wine class is your best bet. In just two hours, you’ll explore the main white and red wines of Tuscany, learn about the different grapes and regions, and taste four or five wines paired with finger foods.
Ideal for travelers who want to understand Tuscan wines better and return home with more confidence in ordering or buying local bottles, this class is held in a central Siena location for easy access. Guests praise the instructor’s enthusiasm and the generous tastings, making it both fun and educational.
Bottom line: A perfect choice for beginners or anyone wanting a guided, relaxed introduction to Tuscany’s most important wines.
4. Total Immersion Wine Tour in Chianti
This Chianti tour offers a hands-on experience in one of Italy’s most famous wine regions. You’ll visit a family-run organic winery, learn about organic wine production, and taste Chianti Classico wines. The tour emphasizes experience over just tasting, with insights into organic farming and wine-making techniques.
What makes this tour stand out is its small size (max group 8), fostering a more personal atmosphere, and the inclusion of cheese, salami, and extra virgin olive oil, which enhances the tasting experience. Guests appreciate the guide’s thorough knowledge and the chance to smell, taste, and learn how to recognize quality wines.
Bottom line: Best suited for those interested in organic wine-making, with a relaxed pace and authentic Chianti experiences.
5. A Brunello Cooking Class with Vineyards View Winery
Combine your love of wine and food with this cooking class. Held on a panoramic terrace, it includes making classic Tuscan dishes like pasta and braised beef, paired with local wines. The experience includes a visit to a vineyard and a 13th-century castle, deepening your appreciation of Tuscany’s history and viticulture.
Rated highly for its informal yet comprehensive format, guests rave about the fun chef Adriana and the delicious meal that ends the class. The tour also includes a wine cellar tour and optional transportation from Siena.
Bottom line: This is ideal for foodies wanting a hands-on experience with excellent wine pairings in a beautiful setting.
6. Tuscany Hiking Tour from Siena Including Wine Tasting
If you’re after a combination of outdoor activity and wine, this hiking tour takes you along the historic Via Francigena, ending with a wine tasting in Monteriggioni. The approximately four-hour walk covers scenic hills, vineyards, and villages, with an expert guide explaining the area’s agricultural history.
Guests love the informative botanical commentary and the relaxed pace, suitable for all fitness levels. The reward is a visit to a local winery and tasting some genuine Chianti wines in a tranquil setting.
Bottom line: Fits travelers who want scenic exercise combined with authentic Tuscan wine tasting, perfect for active day-trippers.
7. Siena walking tour with lunch & Chianti wine
For those seeking a cultural and culinary immersion, this Siena city tour combines exploring Siena’s landmarks with tastings of regional food and Chianti wines. Starting near Basilica of San Domenico, you’ll visit underground caves, medieval alleys, and enjoy a wine tasting with sparkling wines.
Guests enjoy the local stories and hidden gems uncovered during the walk and the hearty Tuscan lunch that follows. It’s a great way to experience Siena’s urban charm and regional flavors in one afternoon.
Bottom line: Best for those who want both history and food on a short guided tour with tastings included.
8. Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch
This full-day tour is perfect for serious wine lovers wanting to visit two of Montalcino’s top wineries and enjoy a pairing lunch in the hill town itself. The itinerary includes cellar tours, tasting Brunello reds, and a scenic drive through Val d’Orcia.
The tour’s value lies in the combination of multiple tastings, a substantial lunch, and seamless transport. Guests highlight the high-quality wines and the opportunity to explore Montalcino’s scenery. The fact that all logistics are handled makes it a stress-free day.
Bottom line: Best suited for those wanting an immersive, full-day experience with expert tastings and regional scenery.
9. Small-Group Chianti Trip with Wine Tasting from Siena
This Chianti tour offers a full-day journey through Tuscany’s most iconic wine region. Visiting Castello di Brolio and Castello di Ama, you’ll taste Chianti Classico wines, explore historic castles, and enjoy a traditional Italian lunch.
Rated highly for its small group size (max 8 people), the tour offers personalized insights and a relaxed atmosphere. Guests love the combination of historic sites, scenic drives, and engaging wine tastings.
Bottom line: A great choice if you want a comprehensive, personalized Chianti experience with cultural and culinary highlights.
10. “CLASSIC” Wine Tasting and Typical Tuscan Products
For a quick, enjoyable taste of Tuscan wines and local delicacies, this classic tasting offers six wines, charcuterie, cheese, and beautiful views from a terrace. It’s an hour-long experience perfect for a relaxed break from sightseeing.
Guests praise the friendly staff, generous tastings, and stunning scenery. It’s especially suited for travelers who want to sample regional flavors without a full-day commitment.
Bottom line: An accessible, informal experience ideal for a quick introduction to Tuscany’s wines and foods.
11. San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
This full-day excursion combines three iconic Tuscan towns with wine and regional cuisine. You’ll explore San Gimignano’s towers, wander Monteriggioni’s medieval walls, and enjoy a lunch with wine tasting at a local winery.
Reviewed positively for its well-organized itinerary and friendly guide, it offers a balance of sightseeing and tasting. Travelers love the flexible free time and the chance to see more than just Siena.
Bottom line: Ideal for travelers who want a comprehensive day trip with sightseeing and wine tasting in a well-structured package.
12. Savor Siena Food and Wine Tour
This foodie tour focuses on Tuscany’s culinary traditions, combining a lesson on regional wines and delicacies with a stroll around Siena. Tasting sheep cheese, olive oil, and local jams, you’ll explore the city’s food scene firsthand.
Guests enjoy the informal atmosphere, friendly guide, and the chance to sample regional specialties in authentic settings. It’s perfect for those who want to combine cultural exploration with flavorful tastings.
Bottom line: Great for foodies wanting a relaxed, in-depth look at Siena’s culinary gems.
13. Siena Underground Wine Tasting in a Medieval Cave
This unique underground wine tasting takes you into a medieval aqueduct beneath Siena’s city center. Savor Brunello di Montalcino and Super Tuscan wines paired with cheese in brick vaults dating back to 600 BC.
Guests love the atmosphere and storytelling, with reviews highlighting the knowledgeable owner and the distinctive setting. It’s suited for those seeking a memorable, atmospheric wine experience close to Siena’s main sights.
Bottom line: A memorable, atmospheric experience that combines history, wine, and a touch of adventure.
14. Chianti and Castle Small Group Tour from Siena with Wine Tasting
This half-day tour explores Chianti’s medieval castles and vineyards, with stops at Castellina in Chianti and Monteriggioni. The highlights include tastings at two wineries and visits to historic sites, all within a small-group setting.
Reviewed for its informative guides and beautiful scenery, this tour balances cultural history and wine tasting effectively. It’s perfect for travelers with limited time but wanting a thorough introduction to Chianti.
Bottom line: An excellent option for a shorter, enriching Chianti experience with personalized service.
15. Pienza, Val d’Orcia, Montalcino Wine and Pecorino Cheese Private Tour from Siena
Finally, for those seeking a luxurious, customizable day, this private tour offers personalized visits to Pienza, Montalcino, and Val d’Orcia. You’ll enjoy wine tastings in top-rated wineries and savor fresh Pecorino cheese in small towns.
Rated highly for Roberto’s expert guidance and the flexibility of an private itinerary, it’s ideal for travelers who prefer an exclusive experience, with the comfort of hotel pickup and drop-off.
Bottom line: Perfect for couples or groups seeking an intimate, tailored day with premium wines and local food.
How to Choose the Right Wine Tour in Siena
When selecting a wine tour, consider your budget, interest level, and time availability. For a full immersion into Brunello, the Brunello di Montalcino Wine Tour is unbeatable. If you prefer a shorter, more casual experience, the Classic Wine Tasting provides quick access to local wines and scenery.
For those wanting a hands-on experience, the Cooking Class is ideal. Active travelers might enjoy the Hiking Tour, which combines walking with tastings. Budget-conscious visitors will find the Affordable Tasting appealing, while those craving exclusivity might prefer the Private Tour.
Always book early, especially in high season, to secure your preferred date and time. Consider the tour length, group size, and whether transportation is included when making your choice.
Final Thoughts
Siena’s wine tours offer a fantastic way to experience Tuscany’s flavors and landscapes without the hassle of planning. From relaxing tastings at small family wineries to full-day explorations of Brunello and Chianti, there’s something for every wine enthusiast. If you’re pressed for time, a shorter experience like the Siena wine tour will give you a good taste of regional wines. For more in-depth adventures, the Brunello di Montalcino wine tour or the full private day offer immersive experiences.
No matter your choice, booking ahead ensures you’ll get the most out of your Tuscany visit. These tours provide a perfect blend of wine, food, scenery, and storytelling—a true taste of Siena’s rich viticultural heritage.