Montepulciano is a feast for the senses—rich in wine, food, and scenery. The town’s proximity to rolling vineyards, historic cellars, and scenic countryside makes it a prime spot for memorable tours. We love the wine tastings in authentic cellars that reveal the craftsmanship behind Nobile di Montepulciano and Supertuscan wines—some even accompanied by food pairings like bruschetta or olive oil. For those seeking active fun, the e-bike experiences offer spectacular views without the fatigue, making for a perfect way to explore the Tuscan hills. And if you’re into cooking, the classes on making fresh pasta and tiramisu stand out for their hands-on approach and local authenticity. There’s a little something for all, whether you’re a wine lover, foodie, or outdoor enthusiast.
Quick Overview
Our list includes wine cellar tours (Tasting Tour in One of The Most Beautiful Cellars), e-bike adventures (Wine Tour Ebike Experience), cooking workshops (Cesarine Pasta and Tiramisu Class), and farm visits (Visit to the Cinta Senese farm). Below, we explore each experience, highlighting what makes them special and helping you decide which suits your style.
1. Tasting Tour in One of The Most Beautiful Cellars in the World
This 1-hour wine cellar tour in Montepulciano brings you face-to-face with stunning oak barrels while learning about local winemaking traditions. The experience is small-group, ensuring an intimate setting where you can truly soak up the atmosphere. What makes this tour stand out is the opportunity to taste 3-6 local wines like Nobile, Supertuscan, and Nobile Riserva, paired with bruschetta and extra-virgin olive oil. The guide is highly praised for their humor, knowledge, and storytelling, making it more than just a tasting—it’s a glimpse into Tuscan wine culture. Visitors often comment on how delicious the wines are and how informative the guide was, with a 5.0-star rating from 257 reviews, which speaks volumes about its quality. If you’re after a personalized and authentic experience, this is a top choice.
Bottom Line: Perfect for wine enthusiasts who want an in-depth yet relaxed look at Montepulciano’s winemaking, with excellent reviews and a great value at just over $39.
2. Montepulciano: Wine Tasting and Cellar Tour
For around $37, the Montepulciano: Wine Tasting and Cellar Tour offers a stellar introduction to Tuscan wines. This 1-hour experience includes a walk through a beautifully maintained cellar, where you can admire rows of oak barrels. The guide, Debbie, is known for her infectious passion and engaging storytelling, making the history of Montepulciano come alive. Tasting is paired with bruschetta with olive oil, and the wines—especially the local Nobile—are highly praised, with a 4.8-star rating from 412 reviews. This tour’s strength lies in its combination of history, scenery, and delicious wine, making it great for first-timers or those wanting a relaxed, educational experience. The price reflects excellent value for a memorable hour in Tuscany.
Bottom Line: An ideal choice for those wanting a comprehensive yet affordable wine experience with top-rated guides and a scenic cellar setting.
3. Wine Tour Ebike Experience
E-bikes are transforming how we experience Tuscany, and at number 3 we have the Wine Tour Ebike Experience. This 5-hour adventure combines cycling with tastings, giving you a chance to explore vineyards without tiring out. The electric bikes make hilly terrain manageable, meaning you can reach several wineries and enjoy panoramic views of the landscape. Along the way, you’ll visit scenic spots like Piazza Grande and the Tempio di San Biagio. The route is designed for all fitness levels, and reviews rave about the fun and the guide Enrico, who’s called the best guide ever. The experience includes two wine tastings, helmet protection, and rain gear if needed, making it both practical and fun.
Bottom Line: Best suited for active travelers who want to combine outdoor exploration with vino, and it’s a memorable way to see the Tuscan countryside.
4. Cesarine: Small group Pasta and Tiramisu class in Montepulciano
If you love cooking and authentic food, the Pasta and Tiramisu Class is a wonderful hands-on experience. Over approximately 3 hours, you’ll learn how to prepare two types of homemade Italian pasta and a classic tiramisu, guided by a local Tuscan cook in her home. The class is capped at 12 participants, so you get personal attention and plenty of opportunity to ask questions. The reviews highlight the friendly hosts and the delicious results, with a 5.0-star rating from 111 reviews. The tasting of your own creations paired with wines makes this a memorable culinary highlight.
Bottom Line: Ideal for food lovers eager to learn family recipes in a cozy setting, and it provides skills you can recreate at home.
5. Tuscan Cooking Class – Traditional 5 course menu
For a more comprehensive culinary experience, the Tuscan Cooking Class offers a full 5-course meal. Led by Giacomo, this 5-hour class covers appetizers, two pasta courses, and a dessert, all made from scratch. You’ll also enjoy local wines during the cooking process and then sit down to eat your handiwork. This class is well-loved, with guests praising the chef’s passion and the chance to learn traditional Tuscan recipes. Priced at just under $283, it’s a bit more expensive but offers exceptional value for a hands-on, in-depth culinary experience that ends with a feast.
Bottom Line: Perfect for serious foodies who want a comprehensive cooking experience with the chance to learn multiple dishes and enjoy them with wine.
6. Visit to the Cinta Senese farm in Montepulciano
A visit to Roberto’s farm (Cinta Senese pigs) offers a rural escape into Tuscan farm life. The 1.5-hour tour includes walking through vineyards, olive groves, and meeting Roberto’s prized pigs—especially the famous Cinta Senese breed. Visitors often call it an unforgettable experience, and the farm-to-table lunch with homemade wine, meats, and cheeses is a highlight. The farm is a real working operation, with a focus on sustainable practices and animal welfare, which shines through in the enthusiastic reviews. It’s an authentic way to understand the land, food, and farming traditions of Tuscany.
Bottom Line: Ideal for travelers interested in agriculture, local food production, and farm life, with a tasty tasting included.
7. Tuscan Cooking Class – Traditional Pasta Menu
If you want to master fresh pasta from scratch, this Pasta Menu Class is a great fit. Led by Chef Giacomo on his farm, the 3.5-hour session covers making pici and ravioli, plus sauces and appetizers. The relaxed setting allows for personalized instruction, and you’ll get to taste the dishes you make paired with local wines. Reviews rave about the quality of the food and the chef’s expertise, with many saying it’s a highlight of their Tuscany trip. It’s perfect for those who want an immersive, hands-on cooking experience.
Bottom Line: Best suited for those seeking authentic Italian pasta skills in a friendly farm environment.
8. Montepulciano: Artisan Heroic Wine Tasting at the Terrace
The Artisan Heroic Wine Tasting is a 1.5-hour tour that combines nature, tradition, and high-quality wine. Held on a terrace with stunning views, it features tasting 3 natural cru wines alongside assorted local products (“Tagliere”). The host, Andre, is praised for his lively presentation and depth of knowledge. Guests enjoy sampling wines in a setting perfect for a sunset toast. It’s a well-reviewed experience for those wanting a refined, picturesque wine tasting with a focus on artisanal wines.
Bottom Line: Great for lovers of natural wines and scenic views, with a warm, personal touch.
9. Italian Wine Tasting with Professional Sommelier in Montepulciano
For a more structured wine experience, this Sommelier-led Tasting offers an overview of up to nine different varietals, paired with snacks. The 2-hour 15-minute experience is hosted by Francesco, whose passion and expertise shine through. Guests learn about regional differences in Tuscan wines and enjoy tasting in a relaxed cellar setting. At just under $80, it’s a great value for a comprehensive tasting with professional guidance. The reviews highlight how much guests learned and enjoyed the personalized approach.
Bottom Line: Perfect for those ready to dive deep into Italian wines with an expert in a friendly atmosphere.
10. Montepulciano: Wine Tasting & Lunch in a Typical Winery
This Wine Tasting & Lunch offers a full experience: tour an ancient cellar, taste 4 local wines, and enjoy a Tuscan lunch. The 1.5-hour tasting showcases region-specific wines paired with local products, and the meal provides a satisfying conclusion. Many reviews praise the informative guide and the stunning landscape views. At just over $62 per person, this experience offers great value—balancing wine, food, and scenery in one package.
Bottom Line: Ideal for travelers wanting a comprehensive taste of Tuscany—wine, food, and landscape—without sacrificing quality.
11. Montepulciano: Winery Tour and Tasting
A 1.5-hour guided tour of a historic 16th-century cellar opens the door to prestigious Tuscan wines. The guide shares detailed insights into the winemaking process, and the tasting includes appetizers paired with the wines. Reviewers mention the generous and educational experience, emphasizing the cellar’s historic charm. This tour is suited for those who want a deeper understanding of wine production and the region’s traditions, with a price of $40 offering solid value.
Bottom Line: Excellent for wine aficionados interested in history and craftsmanship.
12. Montepulciano: Winery Tour & Tasting Experience
This underground 16th-century Etruscan cellar tour combines history, architecture, and wine. Tasting four wines, including Nobile di Montepulciano, is complemented by local appetizers. Reviewers love the unique atmosphere and the informative guide who explains the cellar’s history and methods. This experience is best suited for those interested in ancient wine storage and traditional production techniques. Priced at just over $40, it offers a rich, educational experience.
Bottom Line: A top pick for history-minded wine lovers who want to see an Etruscan cellar firsthand.
13. Horseback Riding Tour with Tuscan Picnic in Val d’Orcia and Valdichiana
For an active, scenic experience, this horseback ride and picnic takes you through vines and olive groves with panoramic views of UNESCO-listed landscapes. The 2 to 2.5-hour ride suits all levels and ends with a Tuscan picnic featuring local specialties. Reviewers love the stunning scenery and friendly guides like Davide and Lea. It’s perfect if you want to combine outdoor activity and culinary delights in a relaxed setting, with an experience that balances adventure with comfort.
Bottom Line: Great for outdoor lovers and food fans seeking a laid-back, picturesque outing.
14. Pasta Fresca in Valdichiana Senese
This 3-hour pasta-making class teaches you how to craft fresh pasta and sauces, then enjoy a homemade meal paired with wine. Running in the Valdichiana region, the class emphasizes hands-on learning with a professional chef. Guests highlight the friendly instructor Irene and the delicious dishes they create, which include ravioli and pici. The experience is perfect for families and food lovers who want to take home Italian cooking skills.
Bottom Line: Ideal for those wanting an interactive culinary experience that ends with a satisfying meal.
15. E-Bike Val d’Orcia Experience
This longer, flexible e-bike tour offers 4 to 6 hours of exploring the UNESCO World Heritage site of Val d’Orcia. You can visit villages like Monticchiello and Pienza, taste local ice cream, and shop at small shops—all at your own pace. The reviews praise the helpful staff and beautiful routes. It’s perfect if you prefer total independence and want to customize your day while enjoying the iconic scenery of Tuscany.
Bottom Line: Best for independent travelers with a sense of adventure who want to explore at their own pace.
How to Choose the Right Tour
When selecting a tour, consider your budget, interests, and physical activity level. Foodies might love the small-group cooking classes (Cesarine Pasta and Tiramisu), while outdoor lovers should check out the e-bike adventures (Wine Tour Ebike Experience). Wine enthusiasts will appreciate the deep dives into local cellars (Wine Tasting & Cellar Tours), especially those with historic or artisanal focuses. If you prefer a relaxing scenic experience, the Heroic Wine Tasting on the terrace is superb. For families or those interested in rural life, the farm visit (Cinta Senese farm) offers a genuine connection to Tuscan agriculture.
Booking early is advisable, especially for popular experiences like the cooking classes or e-bike tours, which often sell out in peak season. Check availability in advance and consider the season—spring and fall offer the best weather for outdoor activities.
Final Thoughts
Montepulciano offers a diverse range of tours that can satisfy a variety of interests. Whether you’re drawn to tasting the finest wines, learning to cook Italian classics, or exploring the countryside on a bike, there’s something here for you. For a deep dive into local wine, the small-family cellar tours are a highlight, while the cooking classes bring home authentic recipes and memories. Outdoor enthusiasts will find the e-bike experiences a perfect way to see the landscape, and the farm visits provide a genuine taste of Tuscan rural life.
With so many options, it’s best to decide based on your preferences—budget, activity level, and interest in food or history. Booking in advance guarantees a spot in the most popular tours, so plan ahead and prepare for a memorable trip to Montepulciano.