Siena is a treasure trove for anyone looking to combine great food with rich culture. Thanks to its compact medieval center and lush surrounding vineyards, the city offers a variety of lunch experiences that go beyond just eating. Whether you prefer a quick tasting, a scenic bike ride through the Chianti hills, or a full-day wine tour, Siena has something for every appetite. We’re especially fond of the Siena walking tour with lunch & Chianti wine because it combines city secrets with regional flavors, all in a small-group setting. And for lovers of deeper wine immersion, the Brunello di Montalcino Wine Tour offers a day of exploring iconic wineries with delicious paired lunches.
If you’re serious about wine or want a full day of Tuscan sights, these tours are excellent choices. But if a quick, authentic meal with a local touch is more your style, Siena’s many wineries and guided tastings won’t disappoint.
Quick Overview
Our list covers a wide range of lunch experiences in Siena, from quick food and wine tastings to full-day tours with visits to famous wineries and charming hill towns. You’ll find options like Siena walking tour with lunch & Chianti wine—great for culture and regional bites—and more comprehensive outings such as the Brunello di Montalcino wine tour, perfect for wine connoisseurs. Whether your focus is historical exploration, wine tasting, or scenic cycling, the list below highlights the best choices for every taste and budget.
1. Siena walking tour with lunch & Chianti wine
At number 1, this 2.5-hour walking tour combines the charm of Siena’s streets with regional food and wine. You’ll explore lesser-known stories and secrets from a friendly local guide, starting near the Basilica of San Domenico and underground medieval caves dating back to 600 BC. The experience includes sampling Pecorino cheese, homemade pici pasta, and regional Chianti wine. The highlight is a wine tasting in Piazza del Campo, which allows you to sip bubbly Prosecco while soaking up Siena’s lively atmosphere. It’s a small-group tour, so your guide can personalize the experience and answer your questions.
This tour is ideal for those who want a quick yet authentic introduction to Siena’s culinary scene, combined with cultural insight. Reviewers love Morad’s friendly attitude and the variety of local dishes. The price of around $100 offers excellent value, considering the food, drinks, and expert guidance included.
Bottom Line: A perfect blend for first-time visitors who want to taste regional specialties and learn about Siena’s lesser-known stories—great for food lovers and history buffs alike.
2. Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch
Positioned second, this full-day winery tour takes you into the heart of Tuscany’s wine country, focusing on Brunello di Montalcino—a world-renowned red wine. The tour includes visits to two historic wineries, a scenic drive through the Val d’Orcia, and a delicious lunch in Montalcino paired with local wines. You’ll tour centuries-old cellars and learn about the meticulous process that makes Brunello special. The small group ensures a personal experience, with plenty of time to ask questions and savor the wines.
Guests consistently praise the expert guides and the opportunity to buy bottles directly from boutique wineries. The $371 price includes tastings, lunch, and transport from Siena, making it cost-effective for those serious about wine. The highlight is the quality of the Brunello wines and the chance to explore the picturesque countryside.
Bottom Line: An excellent choice for wine enthusiasts seeking a comprehensive, immersive day in Tuscany’s most famous wine region, with expert tastings and a memorable lunch.
3. Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch
Ranking third, this 8-hour tour is perfect for those eager to explore beyond Siena and dive into Tuscany’s wine and culinary scene. Starting with visits to two boutique wineries, you’ll taste classic Brunello and regional specialties. In Montepulciano, you’ll stroll through medieval streets, take in amazing views of Val d’Orcia, and enjoy a traditional Tuscan lunch paired with local wines. The trip includes hotel pickup and drop-off, so no need to worry about driving.
Guests love the relaxed pace and the opportunity to meet wine producers behind the bottles. The $382 price covers tastings, lunch, and transport—great value for a full-day experience. This tour suits wine lovers who want to combine sightseeing and tasting with a laid-back atmosphere.
Bottom Line: For travelers wanting a comprehensive day of wine, food, and medieval towns, this tour offers a balanced, authentic taste of Tuscany.
4. Chianti and San Gimignano – 2 Wineries with Pairing Lunch
At number 4, this full-day Chianti tour features guided tastings at two distinguished wineries, plus a visit to the UNESCO-listed town of San Gimignano. The lunch in a winery includes regional dishes and wines like Vernaccia and Vin Santo, offering a true taste of Tuscany. You’ll also stop in San Gimignano, famed for its medieval towers and artisan gelato.
The tour balances wine education with sightseeing and cultural discovery. Visitors rave about the guide’s knowledge and the opportunity to sample both reds and whites. At around $324, it’s a good value considering the tastings, lunch, and sightseeing. It’s perfect for those who want to experience Tuscany’s most iconic towns and wines in one day.
Bottom Line: A well-rounded experience ideal for wine and history enthusiasts who want to see Siena’s countryside, taste fine wines, and enjoy medieval architecture.
5. San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
Ranking fifth, this 11-hour guided trip from Florence covers Siena, San Gimignano, and Monteriggioni with free time in each. It includes a lunch and wine tasting at a Chianti winery, plus visits to iconic towns with spectacular architecture and views. The tour offers a rundown of Tuscany’s highlights, with informative commentary along the way.
Reviewers mention how smoothly everything runs, especially the balance of sightseeing and tasting. Price is around $92, making it an accessible way to experience multiple towns with a guide handling logistics.
Bottom Line: Perfect for travelers short on time who want to see the major hill towns, enjoy a wine-tasting lunch, and gain insight from an engaging guide.
6. Small Group E-Bike Chianti Tour with Farm Lunch from Siena
Number 6 appeals to active travelers. This 6-hour E-bike tour takes you through the Chianti hills, with guided stops at a restored monastery and a working farm. The e-bikes make the ride accessible, even for less experienced cyclists, and you’ll enjoy scenic views of vineyards and olive groves. The tour includes a traditional farm lunch with wine tasting, providing an authentic taste of rural Tuscany.
Guests praise the knowledgeable guides and the intimate small-group atmosphere. The $214 price reflects a premium experience for those who love combining activity with food and wine. It’s ideal for adventurous, fitness-minded travelers who want a relaxed but engaging way to see Tuscany.
Bottom Line: For active travelers seeking a scenic ride with authentic farm-to-table food and wine, this is a memorable option.
7. Guided tour of the cellars with wine tasting and lunch
Coming in at number 7, this 2.5-hour tour focuses on the winemaking process at a family-owned winery. Starting from San Giorgio a Lapi, you’ll visit the vineyards, the historic church, and the cellars, where you’ll learn about aging methods. The highlight is a wine tasting on a panoramic terrace with regional cheeses and products.
Guests appreciate the personal touch, with reviews mentioning the guide’s enthusiasm and the scenic views. At $69, it’s an affordable way to deepen your understanding of Tuscan wines without a full-day commitment.
Bottom Line: A good choice for those who want an intimate, educational experience that combines history, art, and wine.
8. VIP Chianti, Brunello wine & Pienza with lunch From Siena
Positioned eighth, this small-group VIP tour offers a personalized experience of Tuscany’s top hill towns and wineries. It includes visits to boutique wineries, a lunch in Pienza, and a scenic drive through the Val d’Orcia. You’ll taste some of the best Chianti and Brunello wines, with free time to explore Pienza’s charming streets.
Guests commend the attentive guides and the exclusive nature of the tour. For around $219, it provides a luxurious, hassle-free way to enjoy Tuscany’s highlights with private transport and tailored experiences.
Bottom Line: Ideal for travelers seeking a premium, intimate day with wine, scenery, and cultural exploration.
9. Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch
Ranked ninth, this vintage Fiat 500 tour combines fun driving with wine tasting and scenic views. You’ll cruise in a classic car through Chianti’s countryside, stopping at a winery for lunch and wine tasting, and exploring picturesque towns like Radda. The small-group experience emphasizes fun and nostalgia, with guides sharing stories about Tuscany’s rural life.
Reviews highlight the unique nature of riding a vintage Fiat and the quality of the winery visit. At about $192, it’s a playful, memorable experience suited for those who love vintage cars and want a relaxed day in the Tuscan hills.
Bottom Line: For a fun, nostalgic way to visit wineries and towns, this tour offers a memorable twist on classic Tuscany exploration.
10. Vespa Tour with Lunch & Chianti Winery from Siena
Number 10 is perfect for those who want a taste of Italy’s iconic style. This Vespa day trip takes you through Chianti’s hills, with options to ride or hop on behind an escort. The lunch at a winery includes wine tasting and local dishes, all while exploring the countryside in a fun convoy.
Guests love the combination of adventure and scenery, though some mention passing the Vespa driving test is required. The $168 price makes it an affordable and exciting option for active travelers who want a hands-on experience.
Bottom Line: Great for travelers looking for a fun, active way to see Tuscany, combined with good wine and regional food.
11. Siena: winery tour, wine tasting and lunch
At number 11, this short 2.5-hour tour is ideal for a quick yet immersive taste of Tuscan wines. Starting at San Giorgio a Lapi, you’ll tour the vineyards and enjoy a lunch with wine tasting on the estate’s panoramic terrace. It’s perfect for those who want a concise experience that combines art, wine, and food.
Reviewers praise the friendliness and delicious food. For about $68, it’s a budget-friendly way to enjoy authentic regional flavors while learning about the winemaking process.
Bottom Line: An excellent, compact experience suited for travelers short on time but eager for quality wine and authentic Tuscan cuisine.
12. Chianti: Lunch with Wine Tasting at Poggio ai Laghi Winery
Number 12 features a cozy, authentic Chianti winery lunch. For approximately 1 hour and 45 minutes, you’ll learn about winemaking and taste a variety of wines, including local favorites like Vernaccia and Vin Santo. The focus here is on the passion and tradition behind each bottle, making this a memorable culinary experience.
Guests appreciate the intimate setting and the personal attention from the wine expert. It’s a great choice for those who want a relaxed, educational wine tasting paired with regional dishes, at a very reasonable price of just $57.
Bottom Line: Perfect for wine enthusiasts who want to learn about Chianti’s wine culture in a relaxed environment.
13. Assisi, Deruta & organic gourmet lunch at the olive oil farmhouse from Siena
Ranked 13th, this full-day tour combines art, culinary delights, and regional crafts. You’ll visit Assisi’s basilica, have a gourmet organic lunch with local olive oil, and explore Deruta’s ceramics. It’s an experience that mixes cultural sightseeing with tastings of olive oil and regional cuisine—an ideal option for those wanting to combine food, art, and spirituality.
Reviews mention the quality of the guide and the memorable meal. The $671 price makes it a premium experience, suited to travelers who want an in-depth, multi-sensory day.
Bottom Line: For those interested in art, spiritual sites, and gourmet food, this tour offers a comprehensive day of cultural and culinary discovery.
14. PRIVATE TOUR: Florence & Chianti in one day with Lunch and Tasting in Winery
Number 14 is a luxurious, customizable option for those wanting to combine Florence and Chianti. This private tour includes panoramic views from Piazzale Michelangelo, visits to two wineries for tastings, and a lunch in Chianti. The flexibility means you can tailor the day to your interests, making it perfect for couples or small groups.
Guests praise the personalized service and the scenic drive. At $289 per person, it’s a premium choice, offering exclusivity and convenience.
Bottom Line: Best suited for travelers seeking a private, tailored experience that combines art, wine, and scenery in one seamless day.
15. Vintage Jeep Tour, Wine Tasting & Lunch
Rounding out the list at number 15, this off-road Jeep tour combines adventure and wine. You’ll explore vineyards in a vintage Jeep, taste Poggio ai Laghi wines, and enjoy Tuscan appetizers. The tour emphasizes art, history, and the landscape, offering a less conventional but equally authentic experience.
Reviewers note the fun of off-road driving and the quality of the wines. The $199 price makes it an engaging, accessible option for adventurous travelers.
Bottom Line: For a lively, fun-filled day with scenic off-road driving and excellent wines, this tour adds a touch of excitement to your Siena lunch experience.
$199.28 per person
How to Choose Your Perfect Siena Lunch Experience
When selecting among these options, consider your priorities: Are you after a full-day wine immersion like the Brunello di Montalcino tour? Or do you prefer a shorter, city-focused tour with regional tastings, such as the Siena walking tour with lunch? For active travelers, the E-bike Chianti tour offers scenery and exercise, while the Vespa or Fiat tours bring a fun, nostalgic twist.
Budget is another consideration: Tours range from budget-friendly options around $57 to luxury experiences at over $370. Think about your interests—wine connoisseur? Opt for the full-day Montalcino or Montepulciano tours. Looking for culture and cuisine? The city walking tour hits all the highlights. Booking early is advised, especially in peak seasons, to secure your preferred date.
Final Thoughts
Siena offers a fantastic variety of lunch experiences that combine food, wine, and culture. For a balanced introduction, the Siena walking tour with lunch is a smart choice. Serious wine lovers should consider the Brunello or Montepulciano tours for deeper tastings and picturesque scenery. If you prefer active fun, the E-bike or Vespa tours deliver both exercise and adventure.
No matter your style or budget, these experiences demonstrate that Siena’s culinary and scenic richness can be enjoyed in many memorable ways. Book early, especially during high season, and prepare to indulge in some of Italy’s best flavors while soaking up the stunning Tuscan landscape.