Monteriggioni is a small medieval hilltop town that packs a surprising punch when it comes to memorable tours. Its rich setting—surrounded by rolling vineyards, olive groves, and ancient walls—makes it an ideal place for immersive activities. Whether you’re interested in tasting world-class wines, exploring historic castles, or learning to cook authentic Tuscan dishes, Monteriggioni offers options that cater to different tastes and budgets. We particularly love experiences like the Lunch with Wine Tasting at Poggio ai Laghi Winery, which combines a delicious meal with expert-guided tastings, and the Horseback Riding Tour through Vineyards, offering a scenic ride through Tuscany’s iconic landscape.
In this guide, we’ll walk you through the nine best tours in Monteriggioni, covering everything from wine tastings and castle tours to organic brunches and horseback rides. Each offers a unique way to experience the charm and flavors of Tuscany, helping you decide which fits your style and schedule best.
What Types of Tours Made the List?
Our list includes a variety of experiences, ensuring there’s something for every type of traveler. For those who love wine and food, there’s the Tuscan Wine Tasting and Local Cheeses and Tasting of Wines, Oils & Vinegars. History and culture buffs can enjoy the Castle Cellar Tour with Wine Tasting, while adventure seekers might prefer the Horseback Riding Tour through Vineyards. For food lovers, the Cooking Class for Dessert & Tuscan Wine Tasting offers hands-on culinary fun, and the Vineyard Golf Cart Tour combines sightseeing with a relaxed lunch.
Below, you’ll find detailed descriptions of each tour to help you pick the perfect fit for your Tuscan adventure.
1. Classic: Lunch with Wine Tasting at Poggio ai Laghi Winery
At number one, this lunch and wine tasting experience combines culinary delight with expert guidance. For around $59 per person, you’ll spend about two hours immersed in the heritage of Poggio ai Laghi, one of Tuscany’s renowned Chianti wineries. The tour includes a hearty Tuscan lunch paired with Poggio ai Laghi’s premium wines, oils, and vinegars. An enthusiastic wine expert will walk you through the tasting, sharing insights about the region’s history and art.
What makes this tour stand out is the combination of a delicious meal with a deep dive into Tuscan wine culture. Guests rave about the quality of the wines and the engaging commentary from the guide. The setting is relaxed yet informative, making it ideal for foodies or anyone wanting a genuine taste of Tuscany. While it’s a bit on the pricier side, the value is clear: a well-rounded experience with excellent food, wine, and storytelling.
Bottom line: A perfect choice if you want a friendly, comprehensive introduction to Tuscan wines paired with local cuisine.
2. Classic: Tasting of Wines, Oils & Vinegars
For just $47 per person, this tasting experience offers an intimate look at Poggio ai Laghi wines, oils, and vinegars over 1.5 hours. It’s ideal for those who want to explore the depth of Tuscan flavors without a full meal. Guided by a knowledgeable wine expert, you’ll sample Poggio ai Laghi’s finest products, complemented by Tuscan appetizers designed to bring out each flavor.
What makes this tour special is the small-group setting, which fosters a relaxed atmosphere and personalized attention. The focus on oils and vinegars alongside wine offers a broader culinary perspective. Reviews highlight the passion of the guide and the exceptional quality of the products. This experience offers great value for those interested in food and wine pairing, especially if you’re short on time but eager to taste the authentic flavors of Tuscany.
Bottom line: Perfect for food and wine enthusiasts who want a rich tasting experience without a lengthy commitment.
3. Tuscan Vineyard Dinner with Wine Tasting
Offering a romantic and scenic dinner, this Vineyard Dinner takes about two hours in Poggio ai Laghi’s stunning vineyard setting. The experience includes a curated selection of Poggio ai Laghi’s premium wines, oils, and vinegars, paired with a delicious Tuscan dinner crafted to enhance each wine’s profile. An expert guides you through the tastings, sharing insights about the region’s art and history.
What makes this experience stand out is its beautiful outdoor setting, perfect for sunset sipping and savoring local flavors. It’s rated highly for the quality of the wines and the ambiance. This tour is best suited for couples or anyone celebrating a special occasion. While the price isn’t specified here, the combination of dinner, wine, and the scenic environment offers excellent value.
Bottom line: Ideal for romantic evenings or special celebrations with a taste of Tuscany’s finest wines and cuisine.
4. Classic: Vineyard Golf Cart Tour & Wine Tasting and Lunch
This Golf Cart Vineyard Tour combines a fun ride through Poggio ai Laghi’s scenic vineyards with wine tasting and a traditional Tuscan lunch. Lasting around two and a half hours, this experience is rated 5/5 by two reviewers, who appreciated its relaxed pace and personable guide.
You’ll explore the vineyard’s landscape from the comfort of a golf cart, then enjoy Poggio ai Laghi’s excellent wines, oils, and vinegars. The lunch includes Tuscan appetizers that perfectly complement the tasting. The tour is perfect for those who want a bit of everything—scenery, wine, and food—without extensive walking or activity. The value is high given the combination of tour, tasting, and meal.
Bottom line: A laid-back but comprehensive way to experience Tuscan vineyards, especially if you enjoy a bit of fun in your wine tour.
5. Tuscan Brunch & Organic Wines
For around two hours, this Tuscan Brunch pairs a hearty local breakfast with organic wines from Monte Chiaro Winery. Led by a certified sommelier, you’ll learn about wine and food pairing while enjoying a selection of family-produced wines and local delicacies.
This tour emphasizes organic and sustainable practices, appealing to eco-conscious travelers. The experience offers insights into Tuscan culinary traditions and includes a relaxed atmosphere ideal for a leisurely morning. Reviewers mention the quality of the wines and the friendly guide, making it a good pick for those interested in organic foods and wines.
Bottom line: Great for a slow, culture into Tuscan organic wine and local breakfast flavors.
6. Chianti: Castle Cellar Tour with Wine Tasting
This 1.5-hour tour, priced at $47 per person, takes you inside a medieval castle’s cellar to explore its history and wine production. You’ll learn about the castle’s role through the centuries and see the tools and techniques used from 1800 to today. The highlight is tasting three wines cultivated in the castle’s own vineyards.
The guided tour offers a detailed look at ancient wine-making methods, providing a tangible connection to Tuscany’s past. The reviews are mixed—some mention the lack of detailed reviews—so it’s best suited for history buffs or those wanting a deeper understanding of wine production techniques. The setting in a castle adds a romantic medieval touch.
Bottom line: Perfect for history lovers who want to combine wine tasting with a glimpse into Tuscany’s past.
7. Chianti: Horseback Riding Tour through Vineyards
For about 1.5 hours, this Horseback Riding Tour offers an active way to see Chianti’s countryside. You’ll ride through vineyards and olive groves, with a short practice session for beginners. Guided by experienced guides, you’ll hear stories about local traditions and history along the way.
This tour appeals to outdoor lovers and those looking for a different perspective on the landscape. Participants should be comfortable with horses and wear suitable clothing—long pants and closed-toe shoes are recommended. The tour is suitable for ages 14 and up and is ideal for those who want a bit of adventure during their Tuscan visit.
Bottom line: An excellent option for active travelers interested in combining nature, history, and a gentle horseback ride.
8. Classic: Tuscan Wine Tasting and Local Cheeses
This 1.5-hour guided tasting experience is a delightful way to explore Chianti wines paired with local cheeses. While the price isn’t specified, the experience emphasizes learning how to match Tuscan wines with traditional cheeses, with a focus on heritage. The expert guide adds layers of art and history to the tasting, enriching your understanding of the region.
Ideal for wine lovers who also appreciate cheese, this tour offers a well-rounded tasting session in a friendly atmosphere. It’s rated without reviews here, but based on similar experiences, expect a personable guide and quality product.
Bottom line: Perfect for those who enjoy wine and cheese pairings and want to learn more about Tuscan culinary traditions.
9. Cooking Class: Dessert & Tuscan Wine Tasting
This three-hour hands-on cooking class is a sweet way to bring home authentic Tuscan flavors. You’ll learn to make Tiramisú and Cantucci, two classic desserts, guided by a chef. Afterward, you’ll enjoy a full meal of the dishes prepared, accompanied by Poggio ai Laghi’s wines, oils, and vinegars.
What makes this experience special is the interactive nature—learning recipes that you can recreate at home—and the opportunity to taste your own creations. It’s suitable for all skill levels and perfect for those who want a memorable culinary experience. The guide’s expertise, combined with the delicious results, makes it a favorite.
Bottom line: Ideal for dessert lovers and home cooks eager to master authentic Tuscan sweets.
How to Choose
Picking the right tour depends on your interests, budget, and schedule. If you’re after a comprehensive wine and food experience, the Lunch with Wine Tasting offers an all-in-one package. For those wanting a shorter, focused tasting, the Wines, Oils & Vinegars is perfect. Adventurers can opt for the Horseback Riding, especially if they enjoy outdoor activities.
If culture and history are your priorities, the Castle Cellar Tour offers a fascinating glimpse into Tuscany’s past. Foodies and families may prefer the Cooking Class, while those seeking a romantic evening might choose the Vineyard Dinner. Consider your interests, physical activity level, and how much time you want to spend—most tours can be booked in advance for peace of mind.
Final Thoughts
Monteriggioni and its surrounds offer a diverse array of tours that cater to wine lovers, history buffs, foodies, and outdoor adventurers alike. If you’re looking for a well-rounded experience, the Lunch with Wine Tasting provides a truly immersive taste of Tuscany. For a more active outing, the Horseback Riding delivers scenic views with a dash of adventure.
Booking early is recommended, especially during peak season, to secure your spot in these popular experiences. Whatever your choice, you’re sure to enjoy a memorable slice of Tuscany that will leave you craving more.
