San Gimignano isn’t just famous for its medieval towers and charming streets; it’s also a top destination for wine enthusiasts. The region offers a mix of traditional wineries, organic farms, and unique experiences like truffle hunting. We especially love tours that combine wine tasting with local food, like the San Gimignano: Wine and Oil Tasting with Tuscan Appetizers because they give a real taste of Tuscany’s culinary heritage. Plus, the breathtaking views of the rolling hills are a perfect backdrop for any wine adventure.
Among the wide selection, some tours stand out for their authenticity, variety, and local focus. Whether you’re after a short tasting or a full-day experience, San Gimignano has options that fit all interests and budgets. Below, we’ll explore each of these carefully chosen wine tours to help you find the perfect match.
1. San Gimignano: Wine and Oil Tasting with Tuscan Appetizers
At number 1, this wine and oil tasting experience offers a one-hour session that can be enjoyed any time after booking. You’ll taste world-class Tuscan wines and extra virgin olive oil directly at the bar, coupled with local Tuscan appetizers. Led by a professional wine expert, guests learn about each blend’s unique characteristics while soaking in stunning views of Tuscany’s vineyard landscapes. The reviews rave about the friendly staff and beautiful location, with many mentioning how this experience made their honeymoon memorable. The cost offers great value for such an immersive tasting that includes multiple wines, olive oil, and charcuterie.
Bottom line: A perfect choice for those wanting a relaxed, informative introduction to Tuscany’s wine and olive oil scene with spectacular scenery as a backdrop.
2. Organic Wine and Food Tasting at Historic Fattoria Majnoni
Next on our list is the Organic Wine and Food Tasting at Fattoria Majnoni, which runs over two hours and includes a guided tour of vineyards and underground cellars. This tour dives into natural, regenerative farming methods and showcases local history. Its unique appeal lies in the hands-on experience of visiting the ancient cellars and learning about organic winemaking. The highlight is the brunch paired with organic wines, cheese, and regional foods. Guests love the stunning landscape views and the chance to see real organic farming in action. The tour’s strong focus on sustainable practices makes it ideal for eco-conscious travelers.
Bottom line: Ideal for those interested in organic wine and learning about regenerative agriculture in an authentic setting.
3. Tuscan Lunch and Wine Tasting in San Gimignano Winery
For about $100, this Tuscan lunch and wine tasting offers a 1.5-hour experience at the magnificent Tenuta Torciano Estate. It’s perfect for those who want to combine food and wine in a scenic setting. The tour includes a farm-to-table meal featuring local cold cuts, pecorino, lasagna, and traditional Tuscan dishes. The small-group atmosphere and the chance to taste homemade wines paired with regional delicacies make it especially appealing. Visitors praise the quaint gardens and vineyards, which add a special touch. The tour is well-suited for a culinary-focused afternoon.
Bottom line: A great pick for foodies who want an immersive meal paired with excellent local wines in a charming setting.
4. San Gimignano: Tasting of Tuscan Wines and Cheeses
This guided wine and cheese tasting lasts about an hour at Tenuta Torciano and is perfect for those who want a focused experience. You’ll sample 5 different cheeses paired with local wines, including extra virgin olive oil and balsamic vinegar. The English-speaking host shares insights on pairing techniques, making it both educational and enjoyable. Reviewers highlight the informative guide and the high-quality wines. It’s a compact yet rich experience for travelers short on time but eager to learn in-depth about wine and cheese pairings.
Bottom line: Ideal for wine and cheese lovers wanting a guided tasting that’s both fun and educational.
5. Experience Tuscan Truffle Hunting with Wine and Lunch
This tour offers a unique outdoor activity—truffle hunting with trained dogs in the Tuscan woods. The Truffle Hunting with Wine and Lunch lasts about 3 to 5 hours and includes learning how to spot black and white truffles. Afterward, enjoy a four-course Tuscan meal with wine, olive oils, and truffle oils. Guests rave about watching the dogs work and the hands-on experience of hunting for truffles. The tour is ideal for those who want more than just wine—it combines culinary tradition, outdoor activity, and local flavors. The inclusion of free parking adds to its appeal.
Bottom line: Perfect for adventurous food lovers keen to experience truffle hunting firsthand with a delicious meal afterward.
6. San Gimignano: Wine, Olive Oil & Balsamic Vinegar Tasting
At Marronaia, this wine, olive oil, and balsamic tasting offers a one-hour guided session with organic, biodynamic products. You’ll taste local wines and homemade olive oils and balsamic vinegar, all while enjoying panoramic views of San Gimignano’s towers. The owner shares insights into the production process, adding educational value. Guests comment on the authentic family atmosphere and the beautiful scenery. It’s an excellent stop for those seeking a relaxed, authentic experience.
Bottom line: Well-suited for travelers wanting a short, authentic tasting with spectacular views.
7. Romantic Dinner and Wine Tasting in San Gimignano Winery
This romantic dinner and wine tasting lasts around 2.5 hours and is perfect for celebrating a special occasion. After a walk around the historic estate, you’ll enjoy a multi-course meal including Tuscan cheeses, truffle lasagna, roasted meats, and vanilla ice cream with balsamic vinegar. The experience includes a tasting of reserve wines and a beautiful setting with live music. Critics rave about the exceptional food and wines and the atmosphere suited for romance. It’s ideal for couples looking for a memorable, elegant evening.
Bottom line: Best for romantic getaways and special celebrations with a focus on food, wine, and ambiance.
8. Private Wine, Evo Oil, Balsamic Vinegar Experience & Meal
For those seeking exclusivity, this private tasting experience takes place at the historic Vernaccia vineyard. It includes a personalized introduction to biodynamic winemaking, followed by a private tasting of wines, olive oils, and balsamic vinegar, paired with delicious regional dishes. The intimate setting and deep land connection make this tour stand out. Reviewers mention the passionate hosts and beautiful vineyard views. It’s ideal for small groups or couples wanting a more personalized experience.
Bottom line: Perfect for travelers wanting an exclusive, in-depth tasting rooted in Tuscany’s land and traditions.
9. San Gimignano: Wine, Oil, Cheese & Balsamic Tasting
This one-hour family-run estate tasting combines organic wines, extra virgin olive oils, aged balsamic, and local cheeses. It offers a panoramic view of San Gimignano’s countryside and an informative host who explains local winemaking traditions. Reviewers appreciate the authentic atmosphere and the variety of tastings in a short period. It’s best suited for short visits or those wanting a taste of multiple products.
Bottom line: An excellent quick, authentic experience that covers the essentials of Tuscan flavors.
10. San Gimignano: Mini Wine Tour with Tuscan Aperitif
This mini wine tour lasts 1.5 hours and includes a guided tour of a vineyard and wine cellar. It features a tasting of 5 wines, including Vernaccia di San Gimignano, paired with a typical aperitif. Guests praise the friendly guides and the opportunity to learn about the wine production process firsthand. It’s suitable for short visits or as part of a larger day of sightseeing.
Bottom line: Great for those wanting a brief but informative taste of local wines and local snacks.
11. San Gimignano: Wine Tasting Experience at Il Colombaio
This wine and olive oil tasting is a scenic vineyard experience lasting 1-2 hours. You’ll enjoy local wines paired with artisanal cold cuts and cheeses. The hosts are passionate and eager to share winemaking stories. It’s an authentic, intimate experience suited for those who want to enjoy Tuscany’s flavors in a relaxed setting.
Bottom line: Ideal for wine lovers seeking a personal, scenic tasting with regional snacks.
12. Christmas Event at Tenuta Torciano: Lunch and Wine Tasting
During the festive season, this Christmas event offers a special holiday lunch paired with top-tier wines. The event features live music and a warm, celebratory atmosphere. It’s perfect if you want to enjoy Tuscany’s holiday spirit along with excellent food and drink.
Bottom line: Best suited for travelers visiting during the holidays who want a festive, memorable experience.
13. Event: Romantic Valentine’s Dinner in San Gimignano Winery
This Valentine’s Day dinner is a special multi-course meal paired with excellent Tuscan wines, including reserve bottles. The evening features live music and a candlelit setting perfect for couples celebrating love. Reviewers describe it as a once-in-a-lifetime romantic outing.
Bottom line: A top choice for romance and celebration, especially for couples seeking a luxurious dinner with wine.
14. Florence: Horseback Riding, Wine Tasting & Cooking Class
Last but not least, this full-day tour combines horseback riding through Chianti, a wine and olive oil tasting, and a cooking class. The 12-hour itinerary is perfect for travelers wanting a comprehensive Tuscan experience. It finishes with a dinner of the dishes you prepared and a visit to the medieval town of San Gimignano. The tour is praised for its balance of outdoor activity, culinary learning, and scenic beauty.
Bottom line: Best suited for adventurous foodies wanting to combine outdoor activities, wine, and cooking into one unforgettable day.
How to Choose Your Perfect Wine Tour in San Gimignano
When selecting a wine tour, consider your budget, time availability, and interests. If you prefer short, educational tastings, options like the Wine and Oil Tasting or Cheese & Wine Tasting are ideal. For those wanting a fuller experience with food and scenery, the Tuscan Lunch or Private Vineyard Tour may be better. Adventure seekers should consider the Truffle Hunting Tour, which combines outdoor activity with culinary delights.
Booking early is always wise, especially during peak seasons like spring and fall. Think about what aligns best with your travel style—whether that’s educational, romantic, adventurous, or gastronomic—and you’ll find a tour that hits the mark.
Final Thoughts
San Gimignano offers a diverse range of wine experiences, from short tastings to full-day adventures with food, outdoor activities, and cultural insights. For a classic introduction, the Wine and Oil Tasting is hard to beat, thanks to its balance of quality, scenery, and friendly guides. If you’re craving a more immersive experience, the Organic Wine and Food Tasting at Fattoria Majnoni provides a deep dive into sustainable farming.
Travelers seeking something special and romantic should explore the Romantic Dinner or the Valentine’s event, both offering memorable settings and exceptional wines. Whatever your style, San Gimignano’s wine tours promise authentic tastes, beautiful scenery, and a true slice of Tuscany.
Make sure to book ahead—these tours fill up quickly, especially during peak seasons. Now, all that’s left is to pick your perfect experience and enjoy a glass of Tuscany’s finest.