Montalcino is a place where wine is woven into the landscape, history, and soul of the region. Known for Brunello di Montalcino, the town offers more than just tasting wines—it’s about enjoying the sights, smells, and flavors of Tuscany. Whether you’re picnicking among rolling vineyards, exploring ancient castles, or tasting rare vintages, Montalcino’s tours promise authentic, memorable experiences. We’re particularly fond of the vineyard picnic with a bottle of wine, which combines stunning views with homemade Tuscan specialties, or the vertical Brunello tasting, perfect for wine lovers curious about how vintages influence flavor.
Quick Overview
On this list, we’ve gathered a diverse selection of tours—from vineyard picnics and tastings to castle visits and olive grove tours. You’ll find options suited for different budgets, time constraints, and interests. If you’re into wine, options like the Brunello wine tasting experience or the winery tour with vertical tastings will satisfy your curiosity. If you prefer a more relaxed day with delicious food, the wine tasting and Tuscan lunch delivers a hearty, authentic experience. For a family-friendly outing, the vineyard picnic with a bottle of wine offers spectacular views and homemade treats.
1. Montalcino: Vineyard Picnic with a Bottle of Wine
At number 1, the Vineyard Picnic with a Bottle of Wine combines the best of Tuscany’s scenic landscapes with genuine, homemade food. This 1.5 to 2.5-hour experience takes place at the Corte Pavone Winery, where you’ll enjoy a private picnic surrounded by lush vineyards. The highlight is sampling local wines and tasting a basket of Tuscan specialties like homemade bread, cheeses, and cured meats, all while taking in sweeping views of Montalcino’s valleys.
Guests love the intimate setting and the personalized attention. One reviewer mentioned how the spectacular scenery enhanced their experience, creating tears of joy for their family. The tour is perfect for those wanting a relaxing, scenic afternoon with good food and excellent wine. It offers great value at $45.55 per person, especially given the private setting and quality food.
Bottom line: Ideal for couples or families wanting a relaxed, authentic taste of Tuscany’s wine country with breathtaking views.
2. Montalcino: Vinyard Tour with Vertical Brunello Tasting
At number 2, the Vinyard Tour with Vertical Brunello Tasting offers a deep dive into how different vintages influence Brunello di Montalcino. This private 1-hour tour takes you through the cellars and vineyards, where you’ll meet the winemakers and learn about the terroir. The highlight is tasting five products, including two vintage Brunellos, which reveals how climate and aging impact flavor.
Guests rave about the opportunity to meet the winemakers and get insider knowledge. This experience is best suited for serious wine enthusiasts interested in vintage comparisons. The intimate setting and personalized approach make it stand out, with the added bonus of exploring the winery’s biodynamic practices.
Bottom line: Perfect for wine lovers wanting a focused glimpse into vintage differences and winemaking techniques, all in an exclusive setting.
3. Montalcino: Wine Tasting and Tuscan Lunch
Coming in at number 3, the Wine Tasting and Tuscan Lunch combines organic wine tastings with a hearty local lunch. Over 2 to 6 hours, you’ll visit a family-run vineyard, walk through organic vineyards, and enjoy hot homemade bread with cured meats and cheeses. The experience is hosted in a beautifully renovated cellar that exudes rustic charm.
Reviewers highlight the warmth of the owner and the authenticity of the meal, often noting the delicious food paired perfectly with their wines. The longer duration allows for a relaxed pace, making it ideal for those who want to savor both the wine and local cuisine.
Bottom line: This is a great choice for those wanting a comprehensive, authentic Tuscan wine and food experience in a cozy, family ambiance.
4. Montalcino: Castle and Vineyards Tour with Tasting
Number 4 offers the Castle and Vineyards Tour with Tasting. Here, you’ll explore a medieval castle and learn how wine production has evolved in the region. The tour includes visiting a historic estate, meeting local winemakers, and sampling local wines paired with local appetizers.
While the tour is shorter—about an hour—guests enjoy the spectacular castle architecture and the intimate setting. The guided visit provides insights into regional history and winemaking techniques that make Brunello special.
Bottom line: Ideal for history buffs and those intrigued by medieval architecture combined with authentic wine tasting.
5. Castiglion Fiorentino: Wine Flight & Charcuterie Board
At number 5, the Wine Flight & Charcuterie Board offers a casual, no-fuss tasting of three selected wines with fresh bread, extra virgin olive oil, and a selection of local cheeses and salumi. This boutique family-run winery boasts wines not available in mass markets, with roots dating back to 1625.
Guests love the personalized attention and the fact that it’s a small, independent operation. The limited wines allow for focused tasting, and the surrounding valley scenery adds to the relaxed vibe.
Bottom line: Perfect for those seeking an authentic, small-scale, high-quality wine experience with a laid-back atmosphere.
6. MONTALCINO: Wine Tasting with Tuscan Cold Cuts and Cheese
Ranked 6th, this Wine Tasting with Cold Cuts and Cheese focuses on Brunello and Rosso di Montalcino paired with local cured meats and cheeses. Tasting directly from barrels and enjoying the spectacular landscape, this two-hour experience offers insight into what makes Montalcino wines so special.
Reviewers mention the passion of the owner and how outstanding the Brunello wines are. It’s ideal for visitors wanting a focused tasting with local food in a scenic setting.
Bottom line: Suitable for those who want to understand wine production and enjoy great regional pairings.
7. Montalcino: Brunello Wine Tasting Experience
Number 7, the Brunello Wine Tasting Experience offers a guided tasting in an elegant medieval castle. Over about 1.5 hours, you’ll learn what makes Brunello di Montalcino unique while savoring three local wines paired with “ciaccini”—a traditional local snack.
This experience is perfect for travelers wanting a refined setting and a guided explanation from a knowledgeable sommelier. Reviewers praise the setting and the tasting quality.
Bottom line: Ideal for those seeking an elegant atmosphere with expert-led tastings.
8. Picnic in the organic vineyards of Brunello
Number 8 features a Private Picnic in the Organic Vineyards. For around two hours, relax in the vineyards with a homemade specialties picnic basket and a bottle of Brunello or Rosso di Montalcino. Guests enjoy spectacular sunset views, with homemade bread and local cured meats enhancing the experience.
Guests describe it as a peaceful, top-quality experience with great service. It’s perfect for those wanting a combination of scenic beauty and culinary delights.
Bottom line: A superb pick for couples or families wanting a laid-back, scenic picnic with wine.
9. Seggiano: Guided Tour of the Olive Grove and Food Tasting
Number 9 explores olive oil production with a guided tour of the olive grove. Over 2-2.5 hours, you’ll learn about sustainable olive cultivation and sample organic EVO oil, along with local foods like cheese, salami, and wine.
Reviewers value the passionate guide and knowledgeable explanations. This experience is suited for those interested in food production and sustainable farming.
Bottom line: Great for culinary enthusiasts who want to understand olive oil and enjoy authentic Tuscan flavors.
10. Montalcino: a unique and engaging tour of the Brunello winery
Number 10’s Winery Tour with Brunello features Land Art in the vineyards, frescoes depicting Montalcino’s history, and a video projection. The 1-hour tour includes walking through the vineyards and cellars, with tastings of Rosso, Brunello, and Brunello Riserva.
This immersive experience combines art, history, and wine for a multi-layered visit. Reviewers appreciate the visual storytelling and beautiful setting.
Bottom line: Perfect for those interested in art and history along with wine.
11. Montalcino: Vineyard Picnic with Rosso di Montalcino Wine
Number 11 offers a Vineyard Picnic with Rosso di Montalcino. Similar to the Brunello picnic, this experience features a private picnic basket with homemade specialties and a bottle of Rosso di Montalcino. Guests relax in the vineyards with views of the Montalcino valleys.
The reviews highlight the peaceful atmosphere and delicious local food, making it a favorite for romantic or family outings.
Bottom line: Excellent for those seeking a casual, scenic picnic with good wine.
12. Montalcino: Winery Tour & Brunello Vertical Tasting
Number 12’s Winery Tour & Brunello Vertical Tasting invites you to taste Brunello from four different vintages. The tour lasts from 45 to 105 minutes and includes a walk through the vineyards and cellar, with a focus on how climate and terroir influence flavor.
Guests find this tour to be insightful and engaging, especially as they compare vintages side by side. It’s a perfect fit for serious wine lovers wanting to understand vintage variation.
Bottom line: Best suited for wine connoisseurs wanting to see how climate impacts taste.
13. Chianciano: Olive Mill Tour with Oil and Food Tasting
Number 13 features a guided tour of an olive mill. In about an hour, you’ll see antique artifacts like a 16th-century wooden press and learn how extra virgin olive oil is made, followed by a tasting of oil, salami, cheese, and wine.
Reviewers appreciate the family’s passion and the quality of the products. It’s ideal for foodies interested in traditional olive oil production.
Bottom line: Perfect for those wanting a short, educational, yet delicious experience.
14. Welcome to Casale del Bosco
Finally, the Visit Casale del Bosco offers a brief vineyard tour and a peek into the aging cellars. The 1-hour experience highlights the interior of their underground cellar and biodiversity, with tastings of their wines.
Guests enjoy the tranquility of the setting and the opportunity to see traditional winemaking up close. It’s suited for those interested in boutique wineries and authentic production methods.
Bottom line: Good for travelers seeking an intimate, behind-the-scenes look at local wine craft.
How to Choose Your Montalcino Tour
When selecting a tour, consider your budget, interest level, and time available. For serious wine tasting and vintage comparison, the vertical Brunello or Brunello experience are excellent. If you prefer a relaxed day with scenic views and good food, the vineyard picnic or Tuscan lunch fit the bill. For families or those on a budget, the shorter castle tour or olive oil tour provide authentic experiences without a hefty price tag.
Booking early is wise, especially during peak harvest season in fall or special events. Also, think about walking ability if visiting castles or vineyards—some tours involve a lot of standing or walking on uneven ground.
Final Thoughts
Montalcino offers a wide range of tours that cater to different tastes, from intimate tastings and food pairings to artistic vineyard visits. If you’re after an authentic taste of Tuscany, the vineyard picnics provide unbeatable views and relaxed atmosphere, while the vertical Brunello tasting is perfect for wine aficionados wanting depth. For families or those craving culinary immersion, the Tuscan lunch is a memorable choice. No matter your preference, booking early will ensure you secure the experience that suits your style and schedule.