Siena is a city that packs a punch when it comes to lunch experiences. Unlike generic tourist spots, Siena offers a mix of culinary delights, historical tasting tours, and scenic winery visits that reflect the true spirit of Tuscany. We especially love the Siena walking tour with lunch & Chianti wine for its blend of discovery and local flavor, tasting regional Pecorino cheeses, homemade pici pasta, and regional wines—plus discovering secrets from a knowledgeable guide. If you’re after a full-day immersion, the Brunello di Montalcino wine tour of 2 wineries with pairing lunch offers exquisite wines, scenic vineyard visits, and a taste of Montalcino’s legendary Brunello. For a more hands-on experience, the Cooking Class: Italian Authentic Recipes with Lunch provides a delicious way to take a piece of Tuscany home with you.
These experiences span a variety of tour styles: from small-group walking tours, wine tastings in historic cellars, full-day winery excursions, to interactive cooking classes. Each offers its own flavor of Tuscany—whether you seek cultural insight, wine mastery, or culinary skills. Keep reading as we explore each top-rated Siena lunch experience in detail.
1. Siena walking tour with lunch & Chianti wine
At number 1, this 2.5-hour guided walking tour combines Siena’s hidden stories with regional tastings. The small-group format ensures personalized attention, and the tour includes a visit near the Basilica of San Domenico, underground medieval caves, and views over the oldest bank in the world. Along the way, you’ll sample organic gelato flavors, regional Pecorino cheese, and homemade pasta called pici, finishing with a wine tasting of local sparkling wines like Prosecco. The guide shares lesser-known tales of Siena’s medieval past, making this a rich cultural experience that also satisfies your appetite. The reviews highlight the friendly hosts and delicious tastings, with many calling it one of the best ways to experience Siena’s authentic flavors.
Bottom Line: Perfect for those wanting an intimate tour combining history, local food, and regional wines—all in just a few hours.
2. Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch
Number 2 on our list offers a full 8-hour day in the vineyards. It focuses on Brunello di Montalcino, one of Italy’s most acclaimed wines. The tour includes a visit to historic wineries with cellar tours, tastings, and a lunch in Montalcino featuring regional dishes paired with Brunello. The drive through Tuscany’s rolling hills with a knowledgeable guide makes the experience both scenic and educational. Guests praise the expert insights into wine production, as well as the chance to purchase bottles directly from boutique wineries. This tour is ideal for serious wine lovers who want a relaxed day with ample tastings, beautiful vistas, and authentic local cuisine.
Bottom Line: A premium, wine-focused experience suited for connoisseurs and those seeking a comprehensive taste of Montalcino’s famous wines.
3. Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch
This 8-hour tour takes you beyond Siena to explore the stunning town of Montepulciano. You’ll visit two boutique wineries, each with its own story, and enjoy Brunello tastings amid centuries-old vineyards. The highlight is a lunch in Montepulciano featuring local specialties paired with regional wines, including the renowned Brunello. You’ll also take time to wander through Montepulciano’s Renaissance streets and admire medieval architecture, finishing with a cheese tasting. Guests love the relaxed pace and the chance to meet winemakers behind the bottles. It’s perfect for those who want a blend of wine, food, and cultural sightseeing.
Bottom Line: An excellent choice for travelers eager to combine wine, medieval towns, and regional cuisine in one full day.
4. Chianti and San Gimignano – 2 Wineries with Pairing Lunch
Number 4 offers a well-rounded 8-hour Chianti experience. Starting with a visit to a Chianti Classico winery near Monteriggioni, you then drive through the Chianti hills, with commentary from your guide. The journey includes a stop in San Gimignano, famed for its medieval towers and gelato, giving you free time to explore. The day concludes with an authentic Tuscan lunch paired with local wines, including Vernaccia and Vin Santo. Reviewers mention the knowledgeable guide, beautiful scenery, and delicious food. The combination of wine, history, and picturesque towns makes this a top pick for those who want a taste of everything.
Bottom Line: Great for couples and small groups wanting a flexible day with wine, sightseeing, and culinary delights in Tuscany.
5. San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
This 11-hour guided tour covers three iconic towns. It offers free time in San Gimignano to explore its towers and art, a visit to Monteriggioni with its medieval walls, and a scenic drive through Chianti. The highlight is a lunch and wine tasting at a local Chianti winery. With a knowledgeable guide providing insights en route, the tour is ideal for travelers wanting an overview of Tuscany’s highlights without the hassle of planning. Reviewers praise the smooth organization and the opportunity to see major towns with professional commentary.
Bottom Line: Perfect for first-timers who want to see the classic Tuscan towns with a relaxed pace and included lunch.
6. Small Group E-Bike Chianti Tour with farm lunch from Siena
Number 6 offers a 6-hour active experience on electric bikes, perfect for those who want to combine sightseeing with a bit of exercise. Meeting in Siena, you’ll bike through quiet Chianti roads, crossing vineyards, olive groves, and shaded forests. The guided ride includes visits to a restored monastery and a farm/winery, where you’ll enjoy a traditional farm-to-table lunch and regional wines. Many reviews emphasize the personalized touch, the stunning scenery, and the ease of e-biking, even for newcomers.
Bottom Line: Ideal for active travelers or families wanting an immersive, scenic tour with a delicious farm lunch.
7. Guided tour of the cellars with wine tasting and lunch
Number 7 is a more intimate experience, focusing on the winemaking process. Starting at the historic San Giorgio a Lapi estate, you walk through vineyards, visit frescoed churches, and explore the cellars to learn how their wines are made and aged. The tour ends with a tasting on a panoramic terrace overlooking the landscape. It’s perfect for those interested in wine production and the artistry behind a good bottle. Guests praise the personable guide and the high-quality wines and food.
Bottom Line: Best suited for wine enthusiasts eager to understand the craftsmanship of Tuscan winemaking.
8. VIP Chianti, Brunello wine & Pienza with lunch From Siena
Number 8 provides a luxurious full-day experience with a small group. You’ll visit boutique wineries in Chianti and Montalcino, enjoy tastings, and explore Pienza’s quaint streets. The tour includes a Tuscan lunch and free time in Pienza, making it perfect for travelers seeking comfort and exclusivity. Reviewers love how personalized and flexible the day is, with many mentioning the breathtaking views and quality wines.
Bottom Line: Excellent for couples or small groups wanting a high-end, personalized wine and cultural tour.
9. Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch
Number 9 offers a fun twist—cruising in a vintage Fiat 500 through Tuscany. This 6.5-hour tour includes a scenic ride past the Siena countryside, with stops in Monteriggioni and a local winery for wine tasting and lunch. Many reviews mention the nostalgic charm and the fun of driving or riding in such an iconic car, along with the beautiful scenery. It’s a unique, photo-worthy experience that blends culture and cuisine in a relaxed format.
Bottom Line: Perfect for travelers craving a bit of nostalgia and memorable photos in Tuscany.
10. Vespa Tour with Lunch&Chianti Winery from Siena
Number 10 is for those who want to see Tuscany in true Italian style—on a Vespa. Over 6.5 hours, you’ll ride through Chianti’s winding roads, stopping at a winery for lunch and wine tasting. The reviews highlight the exhilaration and picturesque scenery, as well as the chance to drive or be a passenger. The tour requires passing a driving test, making it suitable for confident scooter riders.
Bottom Line: Best suited for adventurous travelers who want a fun, scenic way to explore Tuscany’s wine country.
11. Siena: winery tour, wine tasting and lunch
This shorter 2.5-hour experience offers a guided visit to a family-run winery near Siena, including tastings and a typical Tuscan lunch. Guests praise the personalized service, the beautiful scenery, and the delicious food. It’s ideal for those wanting a quick yet authentic wine and food experience that captures the essence of Tuscan viticulture.
Bottom Line: Great for visitors short on time but eager to taste local wines and enjoy a scenic meal.
12. Chianti: Lunch with Wine Tasting at Poggio ai Laghi Winery
Number 12 offers an intimate cozy lunch at a family-owned Chianti winery, with a guided wine tasting. The focus is on learning about winemaking while enjoying regional foods. Many reviews mention the passion of the host and the memorable wine and food pairing.
Bottom Line: Suited for those looking for a relaxed, educational wine and lunch experience in Chianti.
13. Classic: Tuscan Vineyard Lunch with Wine Tasting
This short but sweet experience offers a lunch paired with wine tasting at Poggio ai Laghi vineyard. It provides a quick, authentic taste of Tuscany’s wine culture in a beautiful setting. Ideal for travelers wanting a bite-sized but high-quality experience.
Bottom Line: Perfect as a add-on or for those with limited time who want a taste of Tuscany’s vineyards.
14. Cooking Class: Italian Authentic Recipes with Lunch
Number 14 combines hands-on cooking with lunch and wine tasting. You learn to prepare traditional Italian recipes, then enjoy your creations paired with regional wines. Reviewers enjoy the interactive experience and the opportunity to bring home new skills. It’s perfect for food lovers wanting more than just tasting.
Bottom Line: Best for those who love to cook and want an immersive culinary experience.
How to Choose the Right Lunch Experience in Siena
When selecting your ideal Siena lunch tour, consider your budget, time, and interests. If you’re short on time but want a taste of Siena’s culinary and historic charm, the guided walking tour with lunch offers excellent value. For wine enthusiasts, full-day Montalcino or Montepulciano winery tours provide immersive tastings and scenic views, especially if you love Brunello or Vino Nobile. If you prefer a more active outing, try the E-Bike Chianti Tour for a scenic ride combined with farm-fresh lunch. For a fun, nostalgic twist, the Vintage Fiat or Vespa tours promise memorable adventures with beautiful photo ops. And for those who love to cook, the hands-on cooking class adds a flavorful, participatory element.
Booking early ensures you get your preferred date and experience, especially during peak months in spring and fall. Also, check whether tours include transportation, meals, and tastings to maximize value.
In summary, Siena offers a wide range of lunch experiences—from quick tastings and scenic tours to full-day winery visits and interactive cooking classes. For a balanced mix of time, price, and authenticity, the Siena walking tour with lunch and Chianti wine is a top choice for its blend of history, food, and intimate setting. For wine lovers seeking depth, the Brunello di Montalcino wine tour is hard to beat. And if you want to learn to cook like a Tuscan, the cooking class with lunch is an experience you’ll remember long after the last sip of wine.
Whatever your style, Siena’s culinary scene is sure to satisfy. Don’t forget to book early—these experiences fill up quickly when the weather’s just right!
