Montalcino is a treasure for anyone passionate about wine, food, and authentic Tuscan charm. Its rolling vineyards, historic cellars, and spectacular views make it a perfect backdrop for memorable tours. We love the private vineyard tours, especially those that include vertical Brunello tastings—they give you a real sense of how terroir and vintage influence this world-famous wine. The Tuscan lunch tours stand out for combining wine tasting with delicious local cuisine, making them a great choice for foodies and wine lovers alike. Whether you’re interested in exploring family-run wineries or learning about olive oil production, Montalcino has something tailored for every kind of traveler.
Quick Overview
In this list, you’ll find a variety of wine-focused tours, including private vineyard visits (#1), wine and food tastings (#2), biodynamic experiences (#4), and vertical Brunello tastings (#10). There’s also an olive oil tour (#5) and vineyard picnics (#8) for those seeking a more relaxed experience. Each offers a different slice of Tuscan life—from learning about biodynamic farming to enjoying panoramic vineyard views.
1. Montalcino: Vinyard Tour with Vertical Brunello Tasting
At number 1, this private tour of vineyards ends with a vertical tasting of five Brunello di Montalcino vintages—a real treat for wine enthusiasts. The tour begins with a visit to the cellar and vineyards, where you meet the winemakers and get to see how the grapes are cultivated and processed. The highlight is tasting two Brunello di Montalcino vintages, alongside other wines, giving you insight into how climate and vintage influence flavor. It’s perfect for those wanting an intimate, behind-the-scenes look at a boutique winery. The reviews praise the private, appointment-only tastings, and the chance to discover what makes Brunello so special. This tour offers good value for serious wine lovers eager to compare vintages side by side.
Bottom line: An ideal choice for small groups or couples who want an exclusive, educational wine experience with a focus on vintage differences.
2. Montalcino: Wine Tasting and Tuscan Lunch
Number 2 on our list combines organic wine tasting with a traditional Tuscan lunch—a perfect pairing for food and wine lovers. The tour includes a visit to a beautifully renovated cellar, where you’ll sample organic wines while enjoying the scenic views of the vineyard landscape. The lunch features hot homemade bread, cured meats, cheeses, and a relaxed atmosphere where the family shares their passion. It lasts from 2 to 6 hours, so you can choose a half-day or full experience. The reviews highlight the warm, family-run ambiance and the delicious homemade food. This tour is better suited for those wanting a comprehensive taste of Tuscan hospitality and organic wines at a fair price point.
Bottom line: A well-rounded experience for travelers wanting to enjoy wine, food, and a genuine family setting in Tuscany.
3. MONTALCINO : Wine Tasting with Tuscan Cold Cuts and Cheese
Number 3 offers a tasting of Brunello and Rosso di Montalcino paired with a platter of Tuscan cured meats and cheeses. This experience is set on a small family-owned winery, where you can taste wine directly from the barrel, providing an authentic and immersive experience. The landscape of Brunello surrounds this property, making the setting both picturesque and intimate. Reviewers mention the passion of the owner and outstanding wines. It’s perfect for those who want to understand what makes Montalcino wines unique in a cozy, less commercial environment.
Bottom line: Ideal for wine drinkers wanting a personal touch and a chance to taste wines straight from the barrel in a scenic setting.
4. Exclusive Wine Lesson and Tasting near Montepulciano
Number 4 is a hands-on experience, where you explore Tuscan wines and olive oil with Paolo, a producer who shares 25 years of expertise. This personal, guided tasting includes learning how wines and oils are made, along with tasting the second-best rosé in Europe. The tour features a vineyard walk, a winery visit, and a food tasting at a local restaurant, making it a full sensory immersion. Reviewers appreciate the passion and personal attention from Paolo, describing it as less of a traditional tour and more a cultural experience. If you like learning by doing and want insider knowledge, this is a top choice.
Bottom line: Perfect for curious travelers who want to deepen their understanding of wine, olive oil, and rural life with a personable host.
5. Seggiano: Guided Tour of the Olive Grove and Food Tasting
Number 5 offers the chance to discover how extra virgin olive oil is produced. The tour explores sustainable, family-run olive groves with incredible views of Seggiano. You’ll learn about the production process, taste organic olive oils, and enjoy a food tasting that includes local specialties. Many reviews praise Elena’s passionate explanations and the complexity of olive oil. This experience suits those interested in agriculture and local food traditions, providing insights beyond wine.
Bottom line: An educational, flavorful experience for anyone wanting to understand olive oil’s journey from tree to table.
6. Discover Brunello Wines
Number 6 combines visits to boutique wineries for tastings of exceptional Tuscan products. The tour emphasizes authentic experiences away from tourist crowds, exploring smaller wineries with rich character. It’s a fantastic way to taste top-quality Brunello, Rosso, and local delicacies, with guidance that helps you appreciate what makes Tuscan wine unique. The reviews value the personalized approach and the chance to sample lesser-known gems**.
Bottom line: Best suited for travelers seeking an authentic, less commercialized winery experience that reveals hidden treasures.
7. Montalcino: a unique and engaging tour of the Brunello winery
Number 7 offers a guided visit among Brunello barrels and frescoes depicting Montalcino’s history. The tour includes a video projection and an exploration of art in the vineyards, making it stand out from standard tastings. The frescoes and artistic elements add a cultural layer to the wine experience, appealing to those interested in art and history as well as wine. Reviewers mention the fascinating presentation and the dedication to preserving local tradition.
Bottom line: Perfect for those who appreciate a blend of art, history, and wine in a guided setting.
8. Montalcino: exclusive vineyard picnic with wine
Number 8 offers a relaxed, intimate picnic experience in the vineyards. You’ll enjoy a delicate picnic with Tuscan specialties while soaking up spectacular views. This is perfect if you prefer a casual, scenic experience where the focus is on enjoying the landscape and local flavors. Reviewers describe it as magical and exclusive, ideal for couples or small groups seeking a private, memorable moment in the countryside.
Bottom line: Excellent for those wanting a laid-back, picture-perfect picnic amid Tuscany’s vineyard scenery.
9. Montalcino: Vineyard Picnic with Rosso di Montalcino Wine
Number 9 is a private picnic experience that combines Tuscan specialties and Montalcino wines, including Brunello or Rosso di Montalcino. The experience offers a relaxing setting with breathtaking views of the valleys. The picnic basket includes homemade bread, cured meats, and cheeses, perfect for unwinding after a day of exploring. Reviewers love the sunset views and the personalized service.
Bottom line: Ideal for travelers looking for a luxurious, scenic picnic with top-notch wine and local bites.
10. Montalcino: Winery Tour & Brunello Vertical Tasting
At number 10, this guided winery tour focuses on comparing Brunello across four vintages. You’ll visit Corte Pavone, walk through vineyards, and enjoy a 45-minute tasting of different vintages, illustrating how climate and age influence flavor profiles. The winery emphasizes biodynamic philosophy and sustainable practices. Reviewers mention the insightful comparison and stunning views of Montalcino as highlights. It’s great for those interested in wine aging and terroir.
Bottom line: A must for serious wine fans wanting to understand how vintage shapes Brunello’s character.
11. Chianciano: Olive Mill Tour with Oil and Food Tasting
Number 11 offers a guided tour of an olive mill, including artisanal oil tasting and local products like salami, cheese, truffle, and wine. You’ll see an antique wooden press and learn about olive oil craftsmanship. Many reviewers praise the family-run atmosphere and educational approach. It’s an excellent option for those curious about olive oil production and wanting a food-focused experience in Tuscany.
Bottom line: Suitable for travelers eager to explore olive oil as a key part of Tuscan culinary tradition.
12. Tenute Silvio Nardi: wine tour of 30 years of Brunello
Number 12 takes you through 30 years of Brunello evolution at Tenute Silvio Nardi. The private tour includes visits to vineyards and aging cellars and a tasting of seven wines, showcasing the development of the winery’s signature style. Reviewers note the magnificent interior and the biodiversity of the estate, making it ideal for wine enthusiasts interested in history and craftsmanship.
Bottom line: A comprehensive experience for those wanting to trace Brunello’s journey through time.
13. Welcome to Casale del Bosco
Our final pick, number 13, offers a short, engaging tour of vineyards and underground cellars. It’s perfect if you want a quick overview of Montalcino’s wine production without a long commitment. The biodiversity and beautiful cellar interior make it a charming, accessible introduction to local wines.
Bottom line: Suitable for travelers with limited time looking for a taste of Montalcino’s wine culture.
How to Choose the Right Tour
When selecting a tour in Montalcino, consider your interest level—are you looking for deep dives into Brunello vintages (#10), culinary experiences like lunch and food tastings), or educational olive oil tours (#5)? If your time is limited, the shorter winery visits (#7) or welcome cellar tours (#13) are perfect. For those wanting more immersion, tours combining vineyard walks, tastings, and meals (#2) are invaluable. And don’t forget to check availability and book early—these experiences fill fast, especially in high season.
Final Thoughts
Montalcino offers a range of experiences—from vertical Brunello tastings to scenic picnic tours—ensuring every traveler finds something memorable. For serious wine fans, #10 delivers a detailed vintage comparison, while #2 offers a hearty taste of Tuscan hospitality. Art lovers will appreciate the artistic touches of the winery #7), and foodies will enjoy the olive oil and food tastings (#5). Booking in advance is wise, especially for private or popular tours, so plan accordingly.
Whichever experience you choose, immerse yourself fully—Montalcino’s charm lies both in its wines and its landscape. Cheers to your Tuscan adventure!