The historic city of Siena serves up some of Italy’s finest lunch experiences, all within easy reach of its medieval center. The standout options combine great food with unforgettable activities. In nearby Montepulciano and Montalcino, winery tours offer the perfect mix of famous Tuscan wines paired with local specialties. Taking an e-bike through the rolling Chianti countryside leads to a fantastic family-style lunch that’s worth every pedal. For a classic Italian touch, zip around in a vintage Fiat 500 to visit local wineries and enjoy lunch at your own speed. The olive oil experience stands out for teaching visitors about premium Tuscan oils, followed by a wonderful country lunch. My favorite choice combines a morning walking Siena’s narrow lanes with an afternoon wine tasting and hearty lunch at a Chianti farmhouse.
These top food-and-wine adventures give you the real taste of Tuscany.
Key Points
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Guided Siena Tours with Winery Lunch offer a 9-hour small group tour focused on Siena’s attractions, culminating in a gourmet Brunello wine-paired lunch.
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Fully Escorted Tuscan Adventures include a delightful Tuscan lunch with local specialties like pecorino cheese and homemade dessert at a Chianti winery.
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Brunello di Montalcino Wine Tours and Chianti Wine Tours both feature a traditional Tuscan lunch as part of their wine tasting experiences.
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The EVO Oil Experience includes a freshly prepared meal in addition to an in-depth exploration of high-quality extra-virgin olive oils.
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Private Tuscany Tours incorporate a farmhouse wine tasting and Tuscan lunch in the Chianti region as part of their personalized excursions.
Vespa Tour With Lunch & Chianti Winery From Siena
The allure of a Vespa tour through Tuscany‘s picturesque Chianti hills has long captivated visitors to Siena. This full-day experience offers the opportunity to explore the countryside on a Vespa, guided by professionals.
The tour includes visits to vineyards, a wine tasting, and a light lunch, all for $139.10 per person. While the experience highlights riding through charming villages, mixed reviews suggest issues with safety, training, and logistics.
Participants should have a valid international driver’s license and be prepared for potential damages. The Vespa tour promises a unique way to discover Tuscany’s beauty, but customers should weigh the pros and cons based on their preferences and abilities.
Read our full review: Vespa Tour With Lunch & Chianti Winery From Siena Review
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Siena: EVO Oil Experience With Walk, Tasting and Lunch
For those seeking an immersive dive into Tuscany’s renowned extra-virgin olive oil culture, the Siena: EVO Oil Experience With Walk, Tasting and Lunch offers an unparalleled opportunity.
This 3-hour activity includes a guided tour through a 17th-century olive grove, a tasting of the farm’s exceptional EVOs, and a freshly prepared meal showcasing the oil’s unique qualities.
Led by a local producer, the experience provides an in-depth look at traditional Tuscan cultivation methods and the art of recognizing high-quality oils.
Priced at $68.76 per person with free cancellation up to 24 hours in advance, this immersive olive oil experience is a must for any foodie visiting Siena.
Read our full review: Siena: EVO Oil Experience With Walk, Tasting and Lunch Review
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Full-Day 2 Wineries Tour in Montepulciano With Tasting and Lunch
Exploring Tuscany’s renowned wine region, this full-day tour offers an immersive experience visiting two or three local wineries in the charming town of Montepulciano.
With a maximum group size of 8, guests enjoy personalized attention and the opportunity to learn about wine production while tasting regional specialties, including Brunello.
The tour includes hotel pick-up and drop-off, transportation in a luxury vehicle, and a traditional Tuscan lunch served at one of the wineries.
While the overall experience is praised by 95% of travelers, some feedback suggests room for improvement in communication and lunch quality at certain wineries.
Nevertheless, this tour is widely regarded as a must-do for wine enthusiasts visiting Tuscany.
Read our full review: Full-Day 2 Wineries Tour in Montepulciano With Tasting and Lunch Review
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From Siena: Chianti Countryside E-Bike Tour W/ Lunch & Wine
Departing from the charming city of Siena, this 6-hour e-bike tour offers an immersive journey through the captivating Chianti countryside.
Limited to just 8 participants, the tour provides guided access to scenic vineyards, olive groves, and the historic 13th-century fortress of Monteriggioni.
Riders will cover approximately 20km of secondary roads, with e-bikes ensuring an accessible experience for all fitness levels.
The highlight of the tour is a farm lunch featuring local wines and seasonal products.
With an overall rating of 4.8/5 from 39 reviews, this tour combines adventure, stunning landscapes, and the flavors of the Tuscan region.
Read our full review: From Siena: Chianti Countryside E-Bike Tour W/ Lunch & Wine Review
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Brunello Di Montalcino Wine Tour of 2 Wineries With Pairing Lunch
Travelers embarking on the Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch can expect an immersive journey into the heart of Tuscany’s renowned wine region.
The tour offers a specialization in Brunello di Montalcino, with visits to historic wine cellars and vineyards in Montalcino and Montepulciano. Guests will enjoy a pairing lunch at a historic winery, complemented by the region’s exceptional wines.
The tour accommodates a maximum of 8 travelers, ensuring a personalized experience guided by English-speaking professionals.
While some travelers noted minor itinerary discrepancies, the overall experience is praised for its breathtaking Tuscan scenery, knowledgeable guides, and exceptional wine and food pairings.
Read our full review: Brunello Di Montalcino Wine Tour of 2 Wineries With Pairing Lunch Review
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From Siena: Brunello Di Montalcino Guided Wine Tour W/ Lunch
For those seeking a deeper immersion into Tuscany’s renowned Brunello di Montalcino wine region, the From Siena: Brunello Di Montalcino Guided Wine Tour W/ Lunch offers an exceptional opportunity.
This 9-hour guided tour takes participants to three local wineries, where they’ll enjoy tastings and meet the winemakers. Visitors will also explore the charming town of Montalcino and visit the Abbey of Sant’Antimo.
The highlight is a traditional Tuscan lunch at a family-run winery, featuring regional dishes and wines. With roundtrip transportation from Siena, an English-speaking guide, and a small group size, this tour provides an intimate and immersive experience in the heart of Brunello country.
Read our full review: From Siena: Brunello Di Montalcino Guided Wine Tour W/ Lunch Review
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Small Group E-Bike Chianti Tour With Farm Lunch From Siena
Explore the picturesque Chianti countryside on an exhilarating small-group e-bike tour from Siena.
This full-day tour offers the chance to visit a restored monastery, a local farm and winery, and enjoy a traditional Tuscan meal accompanied by generous wine tastings.
With a maximum group size of 8 travelers, you’ll benefit from personalized attention and guidance from a professional guide.
Though not wheelchair accessible or suitable for those with health concerns, the tour is recommended for active travelers aged 14 and up who are comfortable riding an e-bike.
Receive complimentary use of the bicycle and helmet, as well as bottled water, during this highly-rated 4.8-star experience.
Read our full review: Small Group E-Bike Chianti Tour With Farm Lunch From Siena Review
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From Siena: Chianti Wine Tour With Lunch
Why not embark on an exhilarating Chianti wine tour from Siena that offers a delightful blend of scenic countryside, historic wineries, and a traditional Tuscan lunch?
This 8-hour tour, limited to just 8 participants, takes you on a journey through the picturesque Chianti region. You’ll visit local wineries, learn about the winemaking process, and indulge in tastings of the region’s renowned red wines.
The highlight is a traditional Tuscan lunch served with wine, allowing you to savor the flavors of the local cuisine.
With an expert guide, roundtrip transportation, and the flexibility of free cancellation up to 24 hours in advance, this tour promises an unforgettable wine-tasting experience.
Read our full review: From Siena: Chianti Wine Tour With Lunch Review
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Vintage Fiat 500 Tour From Siena: Tuscan Hills and Winery Lunch
Embarking on a Vintage Fiat 500 tour from Siena offers an exhilarating way to discover the enchanting Tuscan hills. The small-group tour whisks you away in the classic Italian car, driving through Chianti’s rolling vineyards and visiting the medieval village of Monteriggioni.
Refueling with a winery lunch at Poggio Amorelli, you’ll savor a 3-course meal and wine tasting.
While the tour promises beautiful scenery and a unique driving experience, some participants have reported logistics issues and mixed guide engagement.
Nevertheless, with included transportation, lunch, and tastings, this vintage tour provides a delightful way to learn about Tuscany’s charm.
Read our full review: Vintage Fiat 500 Tour From Siena: Tuscan Hills and Winery Lunch Review
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Siena: E-Bike Tour in the Chianti Senese With Lunch
Visitors looking to discover the picturesque Chianti Senese region can enjoy a 7-hour e-bike tour from Siena.
The tour takes participants through scenic roads, with stops at Tolfe, Colle Pinzuto, and San Giovanni a Cerreto. Riders will explore vineyards, olive groves, and medieval villages, while enjoying an effortless e-bike experience.
The tour includes a guided visit to a Chianti estate for wine and cheese tastings, accompanied by a traditional Tuscan lunch.
With a maximum group size of 10 and flexible cancellation policies, this tour offers a unique cultural experience and an opportunity to savor the flavors of the Chianti Senese.
Read our full review: Siena: E-Bike Tour in the Chianti Senese With Lunch Review
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Chianti and San Gimignano – 2 Wineries With Pairing Lunch
On a day spent exploring the Chianti wine region, travelers have the opportunity to experience two renowned wineries, savor a gourmet Tuscan lunch, and discover the medieval charm of towns like San Gimignano or Monteriggioni.
This full-day tour includes round-trip transport, two winery visits with tastings, and a lunch featuring local specialties paired with wine.
With an English-speaking driver-guide, a maximum of 8 travelers, and amenities like bottled water and air-conditioning, the experience promises an intimate and enjoyable day.
Priced at $268.50 per person, the tour has received overwhelmingly positive reviews, though some note a rushed pace and mixed opinions on the quality of the lunch.
Read our full review: Chianti and San Gimignano – 2 Wineries With Pairing Lunch Review
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Private Tuscany Tour to Siena and San Gimignano With Lunch
Travelers seeking a more personalized Tuscan experience can enjoy the rich history and stunning landscapes of Siena and San Gimignano on this private tour.
Priced at €500 per person, the 10-hour excursion includes pickup from Florence, a visit to the medieval hilltop town of San Gimignano, and a farmhouse wine tasting and Tuscan lunch in Chianti.
The tour also features a guided exploration of Siena, showcasing the Palio horse race, 17 contradas, and Piazza del Campo.
Highlights include the Torre del Mangia, Duomo, and marble inlaid floors.
Suitable for most travelers, the tour offers an in-depth look at Tuscany’s cultural and culinary treasures.
Read our full review: Private Tuscany Tour to Siena and San Gimignano With Lunch Review
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San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
Embarking on an immersive Tuscan adventure, this fully escorted tour whisks travelers to the picturesque towns of San Gimignano, Siena, and Monteriggioni.
Visitors explore each town independently, with the convenience of round-trip transportation and insights from a knowledgeable tour leader.
The highlight is a delightful Tuscan lunch and wine tasting at a Chianti winery, featuring local specialties like pecorino cheese, penne ragout, and homemade dessert.
Guests can also admire the grandeur of Siena Cathedral.
While the large group size may limit wine tasting experiences, the tour delivers a well-organized opportunity to discover Tuscany’s charm, history, and cuisine.
Read our full review: San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting Review
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Guided Siena Tour With Lunch in Winery – Private Experience
For those looking to delve deeper into the stunning city of Siena, a guided tour with a private winery lunch offers an immersive experience.
This 9-hour small group tour takes visitors to explore Siena’s top attractions, including the Duomo and Piazza del Campo, before heading to a local Brunello di Montalcino winery for a gourmet lunch and wine tasting.
With a certified guide leading the way, travelers can gain in-depth insights into Siena’s rich history and culture.
At the winery, they’ll savor regional specialties paired with the renowned Brunello wines, creating an unforgettable culinary and cultural encounter.
Priced at $190.40 per person, this private experience provides a well-rounded introduction to the best of Siena.
Read our full review: Guided Siena Tour With Lunch in Winery – Private Experience Review
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500 Vintage Tour: Chianti Roads Experience With Lunch From Florence
Venturing through the picturesque Chianti region in a vintage Fiat 500 offers a truly immersive Tuscan experience.
This self-drive tour from Florence allows participants to explore medieval villas, olive groves, and vineyards at their own pace. The tour includes a stop at a local winery for an authentic Tuscan lunch and wine tasting, led by a professional guide.
Participants must have a valid driver’s license and can travel in groups of up to 3 per car.
While reviews highlight the scenic beauty and driving fun, some mention issues with vehicle performance and tour organization.
The opportunity to savor Chianti’s local flavors in a classic Italian car makes this an enticing option for Siena visitors.
Read our full review: 500 Vintage Tour: Chianti Roads Experience With Lunch From Florence Review
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Private Tuscany Tour to Pisa, Siena, San Gimignano and Lunch
This private Tuscany tour takes visitors on an immersive journey through some of the region’s most iconic destinations.
Over 11 hours, guests explore medieval Siena, the picturesque Chianti Hills, historic San Gimignano, and the famous Leaning Tower of Pisa.
The highlight is a wine tasting and Tuscan lunch at a family-run estate, where they savor homemade pasta, salads, cured meats, and regional cheeses.
With a knowledgeable guide, air-conditioned transportation, and the option to skip the line at Pisa’s tower, this comprehensive tour offers a seamless and enriching Tuscan experience.
While the lunch is described as basic, the tour’s overall quality and service receive positive reviews from previous guests.
Read our full review: Private Tuscany Tour to Pisa, Siena, San Gimignano and Lunch Review
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Club Brunello Private Tasting With Lunch in a Castle Winery
Visitors seeking an immersive Tuscan wine experience can indulge in the Club Brunello Private Tasting with Lunch in a Castle Winery.
Situated in Siena, this 5-star rated activity offers a private tour of a castle winery, a delectable 3-course Tuscan lunch with Rosso and Brunello wine pairings, and Tuscan snacks.
Priced from $269.58 per person, the experience includes private transportation and alcoholic beverages.
The activity is for individuals over 18 and not wheelchair accessible, but most travelers can participate.
With free cancellation up to 24 hours prior and a reserve now, pay later option, this exclusive winery tour is a must for wine enthusiasts visiting Siena.
Read our full review: Club Brunello Private Tasting With Lunch in a Castle Winery Review
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PRIVATE TOUR: Florence & Chianti in One Day With Lunch and Tasting in Winery
Travelers seeking a comprehensive Tuscan experience can embark on a private tour that combines the rich history and iconic sights of Florence with the tranquil beauty of the Chianti region.
Priced from $269.58 per person, this full-day excursion offers air-conditioned transportation, a 3-course lunch at a typical Tuscan farm, and five wine tastings featuring local varietals.
Pickup is provided from the traveler’s hotel, apartment, or private address, and the tour is accessible to most participants, including those with strollers or wheelchairs.
With a 5.0 rating from past travelers, this tour promises an immersive exploration of Florence and the surrounding Chianti countryside, complete with delicious culinary and wine experiences.
Read our full review: PRIVATE TOUR: Florence & Chianti in One Day With Lunch and Tasting in Winery Review
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Frequently Asked Questions
Can I Customize the Tour to Fit My Dietary Restrictions?
Yes, many tour providers in Siena can customize lunch experiences to accommodate dietary restrictions. They’ll work with you to create a personalized itinerary that fits your needs, ensuring you enjoy a memorable dining experience.
What Is the Cancellation Policy for the Tour?
The tour company typically allows cancellations up to 24 hours before the scheduled departure time, with a full refund. Specific cancellation policies may vary, so it’s best to check with the company directly for the most up-to-date information.
How Many People Are Typically in a Tour Group?
Tour group sizes typically range from 8 to 20 people, though some may be smaller or larger depending on the specific tour and operator. The size can affect the overall experience and level of personalization.
Are Children Welcome on the Tour, and Is There a Discount?
Children are welcome on the tour, and there’s often a discount for younger participants. The tour group size can vary, but guides strive to provide a personalized experience regardless of the group’s composition.
Is It Possible to Extend the Tour Duration or Add Additional Stops?
Yes, it’s possible to extend the tour duration or add additional stops. Many tour providers offer customizable options to accommodate visitors’ needs and preferences. However, any changes may incur additional fees.
Recap
Siena offers an array of exceptional lunch experiences for visitors. From Vespa tours with Chianti wine tastings to e-bike adventures through the Chianti countryside, there’s something to suit every taste. Whether you’re interested in exploring olive oil production or indulging in the region’s renowned Brunello wines, Siena provides a delightful culinary journey that perfectly complements the city’s rich history and stunning landscapes.