When visiting San Gimignano, you’ll find several standout tours that make the most of this medieval gem. The intimate wine tastings at Tenuta Torciano are outstanding, offering an authentic peek into Tuscan wine-making traditions. For great value, try the small-group Chianti and Castles Tour – it’s the perfect mix of history, wine, and local flavors.
I’m particularly fond of the e-bike wine tours, which let you experience the stunning countryside while stopping at top wineries. The private walking tours through the historic center are informative and well-paced, giving you the full story of this remarkable hilltop town.
For something unique, the vintage Fiat 500 tours and TukTuk wine adventures offer a fun twist on traditional sightseeing. They’re especially memorable when exploring the surrounding Chianti region.
Let’s explore the best tours San Gimignano has to offer.
Key Points
- Tenuta Torciano Wine Tasting & Tour offers guided tastings of Brunello di Montalcino, Vernaccia, and Chianti Classico, accommodating up to 100 participants.
- Chianti and Castles Tour is a 6-hour small-group tour featuring wine and olive oil tastings with local history insights, limited to 8 participants.
- Private San Gimignano Walking Tour is a highly recommended private tour showcasing UNESCO World Heritage sites, customizable for groups up to 15 people.
- Original Tuscany Wine Tour by TukTuk is a half-day tour priced at $209.33 per person, limited to two passengers for a personalized experience, including a local lunch.
- Tuscany Highlights Tour covers San Gimignano, Siena, and the Chianti region, highly rated with 4.5 stars from over 2,500 reviews, priced at $66.84 per person.
Visit Best Wineries in Tuscany – Wine Tasting & Tour
Although located in the heart of historic San Gimignano, Tenuta Torciano offers visitors a chance to experience the renowned wines of Tuscany.
The winery’s wine tasting and tour provides an in-depth look into the winemaking process, from grape to bottle. Guests can sample a variety of Tuscan varietals, including Brunello di Montalcino, Vernaccia, and Chianti Classico, paired with light Tuscan appetizers or an optional light lunch/dinner.
The guided tour takes visitors through the vineyards and production facilities, offering insights into the region’s winemaking traditions.
With a maximum of 100 participants, the experience provides a personalized and informative session, catering to dietary needs and accessibility requirements.
Praised for its friendly staff, excellent food and wine, and memorable ambiance, the Tenuta Torciano wine tasting and tour offers great value, though some found it slightly commercialized compared to a more in-depth wine education.
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Chianti and Castles Tour From San Gimignano
Nestled in the heart of the historic town of San Gimignano, the Chianti and Castles Tour provides visitors with an immersive experience exploring the renowned wine region of Chianti. Priced at $87.41 per person, this 6-hour small-group tour takes participants on a scenic journey through the rolling Tuscan hills, stopping at the medieval town of Monteriggioni, two local wineries, and the charming village of Castellina in Chianti.
The tour includes guided exploration, wine and olive oil tastings, and the opportunity to learn about the history and traditions of the Chianti region. Guests can savor the flavors of Chianti’s renowned wines made from Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes.
With a maximum of 8 participants, the tour offers a personalized experience and the chance to interact with fellow travelers. Complimentary cancellation up to 24 hours in advance ensures flexibility for participants.
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Wine Tour With Lunch and Wine Tasting
Priced at $79 per person, the Wine Tour with Lunch and Wine Tasting in Guardastelle provides visitors a chance to enjoy the renowned Vernaccia di San Gimignano wine region.
Accommodating up to 16 travelers, the tour offers private transportation, gratuities, and a tasting of 5 wines alongside an olive oil tasting. Guests can expect a culinary experience featuring local Tuscan specialties, including charcuterie, pappa al pomodoro, and regional desserts.
Tour guides educate visitors on the history and production of the area’s signature Vernaccia varietal. With an overall rating of 5 stars, the experience is praised for its informative and friendly staff, stunning views, and high-quality offerings.
The tour is easily accessible, situated just 1 km from San Gimignano, and welcomes guests with confirmed bookings, including those with dietary restrictions and service animals.
This wine tasting tour provides an authentic, immersive opportunity to discover the treasures of San Gimignano’s renowned winemaking heritage.
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San Gimignano: Premium Wine Tour With Lunch
One of the premier wine tours in San Gimignano, this Premium Wine Tour with Lunch offers an exceptional opportunity to take in the region’s acclaimed Vernaccia wine heritage.
Rated 4.5 stars by GetYourGuide, this 6-hour experience combines a guided e-bike tour through the picturesque Tuscan countryside with a visit to a local winery.
During the tour, you will have the chance to explore the charming medieval town of San Gimignano, renowned for its well-preserved towers and stunning vistas.
The highlight of the day is a guided tasting of the area’s renowned Vernaccia wines, accompanied by a delicious Tuscan-style lunch featuring regional specialties.
With transportation and tastings included, this tour provides a seamless and indulgent way to discover the best of San Gimignano’s wine and culinary traditions.
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Private Tour: San Gimignano Walking Tour
For those seeking an in-depth exploration of San Gimignano’s medieval charms, the Private Tour: San Gimignano Walking Tour offers a captivating 100% recommended experience.
This private walking tour, led by knowledgeable local guides, takes visitors through the UNESCO World Heritage-listed city center, showcasing its iconic Romanesque cathedral, the towering Torre Grossa, and the charming Sant’Agostino church.
Along the way, guests will stroll the historic Francigena pilgrimage road, seeing the city’s rich past. Optional activities, like entering the cathedral to admire Gothic frescoes or climbing the Torre Grossa, provide opportunities to delve deeper.
Accommodating groups of up to 15 people, the tour offers customizable itineraries to suit various interests. With morning and afternoon departures available, travelers can seamlessly fit this engaging experience into their San Gimignano exploration.
Concluding in the city center, the tour provides recommendations for dining and further discovery, ensuring visitors make the most of their time in this captivating Tuscan gem.
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From Florence: San Gimignano Winery Tour With Wine Tasting
Travelers seeking an authentic Tuscan winery experience can embark on the From Florence: San Gimignano Winery Tour With Wine Tasting. This half-day tour from Florence to San Gimignano lasts 4 hours and costs from Kč 2,048 per person.
Guests will visit a renowned winery that’s been producing wine since 1720. The experience highlights include wine tasting of Tuscan wines and extra virgin olive oil, a meet-and-greet with the winemaker, and a guided tour of the cellars and winemaking process.
Visitors will sample 4 different wines accompanied by local snacks like cheese, bread, olive oil, and cured meats. There’s also free time to explore the gardens and surrounding nature.
Transportation is provided via a free round-trip shuttle service from Florence city center. Dietary requirements should be advised during booking, and guests can purchase wines, oils, and balsamic vinegar directly from the producer with a home delivery option.
With free cancellation up to 2 days in advance, this tour offers an immersive Tuscan winery experience.
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Gourmet Wine Tour San Gimignano Wine Tasting – San Quirico Winery
Situated just 2 miles (3 km) from the medieval town of San Gimignano, the San Quirico Winery offers a private tutored wine tasting experience that delves into the distinctive terroir and winemaking traditions of this renowned Tuscan region.
During the 4-hour tour, guests will explore the winery’s cellar, learn the basics of winemaking, and sample four exceptional Tuscan wines accompanied by bruschetta, salami, and cheese.
The winery’s 12-hectare vineyard produces a range of acclaimed wines, including the Vernaccia di San Gimignano DOCG, Chianti Colli Senesi DOCG, and the San Gimignano Rosso DOC.
Guests can also purchase the winery’s organic extra virgin olive oil, which boasts a 0.1% acidity from its first cold pressing.
Praised by 96% of travelers, the Gourmet Wine Tour San Gimignano offers an intimate, informative experience with knowledgeable hosts, catering to a minimum of 2 people.
With wheelchair accessibility, near public transport, and a flexible cancellation policy, this tour provides an excellent opportunity to take in the flavors of Tuscany.
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San Gimignano Wine Tour From Florence Top Rated Free Shuttle
Although Florence offers a wealth of cultural attractions, visitors seeking to explore the picturesque medieval town of San Gimignano can opt for a convenient wine tour with a free shuttle service.
This popular 12-hour tour departs from Florence and takes guests to San Gimignano, Siena, and the Chianti region, allowing them to experience the highlights of Tuscany. The tour is highly rated, with 4.5 stars from over 2,500 reviews, and it’s booked frequently, with 28 reservations just yesterday.
At $66.84 per person, the tour provides excellent value, including hotel pickup, transportation, and the chance to visit wineries, taste local wines, and savor a Tuscan lunch.
For those interested in a more immersive wine experience, a 7-hour Vespa wine tour with lunch and tastings is also available, though at a higher price point of $205.67 per person.
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Private Tour in San Gimignano
For those seeking a more personalized exploration of San Gimignano’s rich history and medieval architecture, a private walking tour provides an immersive experience.
This 2-hour guided tour takes visitors through the UNESCO World Heritage Site, highlighting Etruscan history and the town’s iconic medieval structures. With visits to the Town Hall, Cathedral, Civic Museum, and the famous big tower, the tour ensures travelers won’t miss any of the top attractions.
Included in the experience are admission fees, wine and ice cream tastings, and optional hotel pick-up and drop-off.
The tour is wheelchair and stroller accessible, though a moderate fitness level is required for the walking. Guides are praised for their knowledge, friendliness, and ability to provide personalized experiences tailored to each group.
With a 5.0 rating from 32 reviews and a 100% recommendation from travelers, this private tour offers an exceptional way to discover the wonders of San Gimignano.
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San Gimignano: Winery Tour With Wine Tasting and Lunch
Travelers seeking an immersive winery experience in the historic town of San Gimignano can embark on a 2-hour tour that promises to delight the senses. Priced from £57.94 per person, this tour takes visitors to a family-run winery near San Gimignano, where they’ll explore the cellar and vineyards while learning about the winemaking process, history, and local curiosities.
The highlight of the tour is the wine and food tasting experience. Guests will sample 5 wines, including Chianti and Grappa, accompanied by a platter of typical local products such as cold cuts, cheeses, first courses, Cantucci, and Vinsanto. A small grappa tasting is also included, allowing visitors to delve deeper into the region’s spirits.
The tour is conducted in Italian and English, and the winery is wheelchair accessible. With a small group size for personalized attention, this experience has received an impressive 4.8/5 rating from previous guests, who praised the delicious food and wine, beautiful setting, and attentive staff.
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Chianti and Castle Small Group Tour From San Gimignano
Tourists visiting San Gimignano can embark on a small-group tour that explores the renowned Chianti wine region. The tour takes participants to two wineries – Castellina In Chianti and Fattoria Lornano – where they’ll enjoy tastings of 7 different local wines paired with traditional Tuscan snacks.
Along With the wine tastings, the tour includes stops in two charming towns, providing a well-rounded experience.
The tour is limited to a maximum of 8 participants, ensuring a personalized experience led by expert multilingual guides. They’ll share insights into the history and winemaking process of the region.
The tour includes comfortable transportation in an air-conditioned minivan or minibus, and an optional pickup service is available for an extra cost.
With an overall rating of 4.1 out of 16 reviews, the tour offers a chance to discover the beauty of Tuscany’s Chianti while indulging in its acclaimed wines and local delicacies.
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Brunello Di Montalcino Wine Tour From San Gimignano
What better way to experience the renowned Brunello di Montalcino wine than on a guided tour from San Gimignano? This 6.5-hour tour takes you to the heart of the Montalcino region, where you’ll visit the historic fortress and explore two local wineries.
Along the way, you’ll learn about the ancient winemaking traditions and techniques that go into crafting these prestigious Sangiovese-based wines.
The tour is priced at $106.95 per person and can accommodate up to 8 participants. You’ll travel by air-conditioned minivan, with the option to be picked up and dropped off at your accommodation within 10 km of San Gimignano for an additional fee.
However, the tour isn’t suitable for wheelchair users, as you’ll need to climb and descend stairs.
While the overall rating is 3.7/5 based on 7 reviews, customers have provided mixed feedback, with some highlighting the knowledgeable guides and beautiful scenery, while others noted limited tastings and a lack of food options.
Keep these considerations in mind when deciding if this tour is the right fit for your Brunello di Montalcino wine experience.
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Private Walking Tour in San Gimignano With a Local Licensed Guide
For those seeking an immersive introduction to the historic town of San Gimignano, the Private Walking Tour with a Local Licensed Guide provides an excellent option.
This private walking tour, which lasts a couple of short hours, is ideal for first-time visitors. Highlights include the iconic Bell Tower, the Church of Sant’Agostino, the Duomo, and the picturesque Cisterna squares.
Personalized to individual tastes and schedules, the tour is led by a knowledgeable local guide who brings the town’s rich history to life. With a 100% recommendation rate from 11 five-star reviews, the tour offers a consistently positive experience, with travelers praising the guide’s expertise and passion.
Private transportation is provided, and Collegiata tickets are included, making for a seamless and enjoyable exploration of San Gimignano’s top sights.
Accessible to wheelchair users and stroller-friendly, this tour is suitable for most travelers seeking an in-depth, personalized introduction to this enchanting Italian town.
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Florence: Wine Tasting and Paring Class Guided Tour
Although the historic town of San Gimignano has numerous sights to explore, visitors seeking a deeper appreciation for Tuscan wine culture can opt for the Florence: Wine Tasting and Pairing Class Guided Tour.
Priced from $47.30 per person, this 1.5-hour experience led by a certified guide allows guests to sample a variety of Tuscan wines, including Chianti Classico, Chianti Classico Reserve, and Tuscan Prosecco or white wine.
The tour also includes a platter of Tuscan appetizers, such as olives, bruschetta, salami, prosciutto, and Parmesan cheese. Guests will learn about the region’s wine production history and receive an educational wine pairing class.
With an overall rating of 4.9/5 and high praise for the personalized wine selection and knowledgeable sommelier, this tour offers an immersive and informative experience for oenophiles.
Travelers can also opt for a VIP experience with a Brunello di Montalcino bottle or request gluten-free or vegetarian menu options.
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Chianti E-Bike Tour From Florence With Wine Tasting
Seeking to explore the picturesque Tuscan countryside beyond the confines of Florence? Consider the Chianti e-bike tour from Florence with wine tasting. This 5-star rated tour takes you on a scenic e-bike ride through the rolling hills of the Chianti region, stopping for a wine tasting and a Tuscan-style lunch.
The tour includes the use of a bicycle and helmet, as well as private transportation to and from the meeting point in San Gimignano. Along the way, you’ll enjoy bottled water and a lunch featuring local specialties like Tuscan cold-cuts, pecorino cheese, and bruschetta.
The wine tasting allows you to sample the region’s renowned vintages. This private tour is ideal for those with a moderate fitness level, though it’s not recommended for those with certain medical conditions.
With free cancellation up to 24 hours before the start, the Chianti e-bike tour offers a convenient and immersive way to experience the beauty of Tuscany. Priced from $272.13 per person, it’s a must-do activity for visitors to the San Gimignano area.
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From San Gimignano: Half-Day Chianti Wine Tour
Set out on a captivating half-day Chianti wine tour from San Gimignano, where you’ll explore the rich winemaking heritage of the region.
Priced at Kč 2,276 per person, this 5.5-hour tour is guaranteed to depart with a minimum of 4 and a maximum of 60 participants, rain or shine.
You’ll enjoy a guided tour led by a local, knowledgeable guide, and participate in a professional wine tasting lesson, sampling 9 different wines, including Chianti Classico D.O.C.G. and Super Tuscan.
The tour also includes tastings of extra virgin olive oil, balsamic vinegar, and local Tuscan products.
You’ll visit the Tuscany Wine Tasting School for 4 wine tastings and an olive oil tasting, then head to a local winery for a guided tour and 3 more wine tastings.
Finally, you’ll have the opportunity to stroll through the picturesque town of San Gimignano before returning.
Roundtrip transportation, an English-speaking tour leader, and more are included.
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From San Gimignano: Original Tuscany Wine Tour by Tuktuk
Travelers seeking a unique and immersive way to explore the Tuscan countryside can embark on the Original Tuscany Wine Tour by TukTuk from San Gimignano.
This half-day tour aboard a charming Ape Calessino (3-wheeled Italian tuk-tuk) takes guests through the rolling hills, vineyards, and cypress forests of the Chianti region.
The tour departs from Poggibonsi, near San Gimignano and Siena, and includes a visit to a local winery.
Here, travelers will enjoy an authentic Tuscan lunch, as well as wine and olive oil tastings. They’ll also have the opportunity to purchase and ship home any local products they’d like.
The tour is led by an English-speaking guide who provides informative commentary throughout.
With a vehicle capacity of two passengers plus the driver, this is a private experience catered to your group.
At $209.33 per person, the tour offers a lowest price guarantee and free cancellation up to 24 hours in advance.
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Private Guided Tour in San Gimignano
For those interested in exploring the historic town of San Gimignano, the Private Guided Tour offers an immersive experience. The 2-hour tour, priced at Kč 3,477 per person, takes visitors through the town’s key sites, including the Cistern Piazza, Civic Museum, Montestaffoli Fortress, and Piazza Duomo.
Along the way, the live English and Italian-speaking guide provides historical context and insights. Highlights of the tour include the option to visit the Rocca di Montestaffoli, taste award-winning ice cream and local DOCG white wine, and witness panoramic views from the Montestaffoli Fortress.
Reviewers have praised the guide’s charisma, extensive knowledge, and ability to engage participants. The tour is wheelchair accessible, and headphones are available for larger groups.
With free cancellation up to 24 hours in advance and a reserve now, pay later option, the Private Guided Tour in San Gimignano is a convenient and immersive way to explore this historic Tuscan town.
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From San Gimignano: Vintage Fiat 500 Self-Drive Chianti Tour
Those seeking a unique adventure in Tuscany can enjoy the Vintage Fiat 500 Self-Drive Chianti Tour. This 4-hour experience allows participants to drive an original restored Fiat 500 through the scenic Chianti countryside.
The tour includes a visit to a Chianti winery for wine tasting and local snacks, as well as the opportunity to explore medieval villages and breathtaking landscapes.
The tour is priced from $132.66 per person and offers free cancellation up to 24 hours in advance. Drivers must be at least 18 years old and have a valid driver’s license.
Groups are limited to 8 participants, ensuring a personalized experience. Reviewers praise the knowledgeable guides and the fun of driving with other couples. However, some note the tour’s transportation and organization could be improved.
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San Gimignano Private Walking Tour
The San Gimignano Private Walking Tour offers visitors an immersive journey through the town’s rich history and architectural wonders.
Lasting 1.5 hours, this guided experience explores San Gimignano’s Etruscan roots and the impact of Attila the Hun, as well as the town’s historical rule under the bishops of Volterra and the Guelphs-Ghibellines conflict.
Participants will discover the medieval charm of this UNESCO World Heritage Site, renowned for its unique skyline of towering medieval buildings.
Priced at $257.09 per group of up to 15 people, the tour includes a local professional guide who can customize the experience on-site.
Meeting at the Porta San Giovanni, the tour is offered in English and Italian, with free cancellation up to 24 hours in advance.
Highlighting the outstanding examples of secular and religious architecture, as well as local products like saffron and white wine, this private walking tour provides an immersive glimpse into San Gimignano’s rich cultural heritage.
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Lucca Private Day Tour to Chianti and San Gimignano
Although visitors to San Gimignano can explore the historic town on their own, the Lucca Private Day Tour to Chianti and San Gimignano offers a comprehensive and personalized experience.
This full-day tour takes travelers from Lucca to the picturesque Chianti region and the iconic town of San Gimignano.
Over the course of 11.5 hours, the tour provides an in-depth look at the area’s rich history, culture, and renowned wine production. Highlights include visits to charming villages, stops at family-owned wineries for tastings, and free time to wander the medieval streets of San Gimignano.
With a small group size and a private driver, the experience is tailored to individual interests and pace.
Rated 4.5 out of 5 stars by over 3,700 reviewers, this tour is an excellent way to experience the best of Tuscany’s countryside and historic towns in a single day.
The price of $61.70 per person makes it a cost-effective option for those seeking an immersive and memorable day trip from Lucca.
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Chianti and San Giminiano Wine Tour – Private Experience
For those seeking an immersive and personalized exploration of Chianti and the historic town of San Gimignano, the Chianti and San Giminiano Wine Tour – Private Experience offers an unparalleled opportunity.
Rated 4.8 out of 5 stars by 64 reviews, this small-group tour takes you on a 9-hour journey from Siena, allowing you to discover the region’s renowned vineyards and picturesque landscapes.
You’ll visit local wineries for tastings and a delectable lunch, while also spending time wandering the charming streets of San Gimignano, a UNESCO World Heritage Site famous for its medieval towers.
The tour’s compact size ensures a more intimate and tailored experience, with the opportunity to ask questions and learn directly from your expert guide.
Whether you’re a wine enthusiast or simply seeking an immersive Tuscan experience, the Chianti and San Giminiano Wine Tour – Private Experience is an exceptional choice, offering a perfect blend of culture, cuisine, and stunning scenery.
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From San Gimignano: Vespa Tour in Chianti
Situated just a short car ride from the medieval town of San Gimignano, the Vespa Tour in Chianti offers an exhilarating way to explore the picturesque Tuscan countryside.
This 4-hour tour allows participants to drive an original Vespa scooter through the scenic Chianti Hills, with a guided tour and time for sightseeing in the charming town of Castellina in Chianti.
The tour also includes a visit to an exclusive winery, where guests can enjoy a guided tour, wine tasting, and local snacks.
Participants must be at least 13 years old, with drivers required to be 18 or older and have a valid driving license. The tour isn’t suitable for children under 12, pregnant women, or inexperienced scooter riders.
With an overall rating of 4.2 out of 5 based on 19 reviews, this Vespa tour promises an unforgettable experience, showcasing the beauty of the Tuscan countryside and offering the thrill of riding a classic Italian scooter.
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The Sum Up
San Gimignano offers a range of tours that allow visitors to explore its historic sights, sample local wines, and experience the Tuscan countryside. Whether it’s a walking tour, a wine tasting, or a Vespa adventure, there’s something to suit every traveler’s interests. With a variety of options available, visitors can create a personalized itinerary to make the most of their time in this picturesque hilltop town.