Medieval towers and wine country meet in San Gimignano, where the best tours combine culture and Tuscan flavors. The most worthwhile experiences include small-group wine tastings at family-run vineyards, where you’ll learn about Vernaccia wine production while sampling local wines and snacks. For something special, vintage Fiat 500 tours wind through Chianti’s backroads, offering an authentic Italian driving adventure. Walking tours of the historic center efficiently cover the main sites and medieval towers in about 2 hours, with guides who know their stuff and skip the fluff. Nature lovers shouldn’t miss horseback rides through the countryside – they’re especially magical at sunset. Check our recommended tours below for the best ways to experience San Gimignano.
Key Points
- Wine tasting experiences in San Gimignano offer immersive tours focused on local cellars, traditional Tuscan aperitifs, and tastings of signature wines and regional specialties.
- Guided vineyard and olive oil tours provide an opportunity to explore the region’s winemaking and production processes, with tastings and educational components.
- Outdoor and adventure tours, such as horseback riding and e-bike tours, combine the natural beauty of San Gimignano with wine experiences for a unique sightseeing experience.
- Guided walking and private tours offer personalized exploration of San Gimignano’s UNESCO World Heritage-listed medieval architecture and landmarks, with opportunities to sample local delicacies.
- Tour logistics and flexibility, including private tours, small group sizes, and flexible cancellation policies, ensure a tailored and convenient experience for travelers.
Visit Best Wineries in Tuscany – Wine Tasting & Tour
For oenophiles seeking an immersive Tuscan wine experience, the wine tasting and tour at Tenuta Torciano in San Gimignano is a must-try.
With a 4.7-star rating from 231 reviews and 92% of travelers recommending it, this activity offers a chance to learn about the winemaking process while savoring a selection of renowned Tuscan varietals.
The tasting session includes a platter of Tuscan salami, cheeses, bruschetta, and dessert, allowing you to discover the perfect food pairings.
You’ll have the opportunity to sample Brunello di Montalcino, Vernaccia, and Chianti Classico wines, all while gaining insights from the knowledgeable staff.
The experience is accessible, with wheelchair and stroller access, as well as infant seats available.
Priced starting at $41.61 per person, the wine tasting and tour at Tenuta Torciano offers a customizable experience, accommodating dietary restrictions.
With hotel pickup and drop-off included, this activity ensures a seamless and memorable exploration of Tuscany’s renowned wine culture.
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Horseback Riding With Wine Tour From Florence
Offering a unique blend of outdoor adventure and oenological exploration, the Horseback Riding with Wine Tour from Florence takes visitors on a captivating journey through the picturesque Tuscan countryside.
Priced at €200 per person, this 7-hour excursion begins with a 1-hour van ride to a nearby horse stable, where participants embark on a 1-hour horseback ride through vineyards and rolling hills, regardless of their prior experience.
The tour then leads to the medieval town of San Gimignano, where guests enjoy 1 hour of sightseeing.
Afterward, they indulge in a 2-hour lunch with a guided wine tasting, savoring the region’s renowned Chianti.
Throughout the experience, an English-speaking guide provides informative commentary, and participants have the opportunity to purchase and ship local products, such as wine, balsamic vinegar, and olive oil.
With convenient hotel pick-up and drop-off options, this tour offers a well-rounded taste of Tuscany’s natural beauty and gastronomic delights.
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Wine Tour With Lunch and Wine Tasting
Nestled just 1 km from the medieval town of San Gimignano, the Wine Tour with Lunch and Wine Tasting offers visitors a chance to escape the crowds and enjoy the serene surroundings of a small family-run estate.
With a maximum of 16 travelers per tour, this intimate experience allows guests to discover the estate’s three estate-made wines through an informative tasting. The tour also includes a delectable lunch featuring local Tuscan specialties like charcuterie, pappa al pomodoro, and dessert. An olive oil tasting adds to the culinary delight.
Praised for its friendly staff and high-quality offerings, the tour has earned a Badge of Excellence and boasts a 98% recommendation rate from travelers.
While not wheelchair accessible, the estate does accommodate strollers and service animals. With free cancellation and a pay-later option, this wine tour is a convenient and highly-rated way to explore the stunning countryside outside San Gimignano.
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San Gimignano: Vineyard and Cellar Tour With Wine Tasting
What better way to experience the charm of San Gimignano’s wine country than with the San Gimignano: Vineyard and Cellar Tour With Wine Tasting? This guided tour offers a 1.5-hour immersion into the region’s winemaking traditions.
You’ll explore the vineyards, visit the wine cellar, and learn about the production process, vinification, and aging techniques. The tasting includes Vernaccia di San Gimignano D.O.C.G, Chianti Colli Senesi D.O.C.G (Vintage and Riserva), and Vinsanto del Chianti D.O.C., accompanied by cured meats, cheese, dried fruits, and olive oil.
With a maximum of 8 participants, this personalized experience promises an intimate and non-touristy atmosphere. Reviewers rave about the knowledgeable staff and the quality of the wines.
Priced at €45 per person, this tour offers excellent value for money. Cancellation is free up to 24 hours in advance, and you can reserve your spot now and pay later.
Don’t miss the opportunity to learn about San Gimignano’s wine heritage.
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Gourmet Wine Tour San Gimignano Wine Tasting – San Quirico Winery
For those seeking an intimate and immersive wine tasting experience in the heart of San Gimignano’s picturesque countryside, the Gourmet Wine Tour at San Quirico Winery is a must-try.
Located just 2 miles from the historic town, this private, tutored tasting offers visitors the chance to sample four Tuscan wines paired with bruschetta, salami, and cheese.
The experience begins with a tour of the winery’s cellar, where guests will learn about the region’s winemaking techniques.
Visitors will then have the opportunity to taste the Vernaccia di S. Gimignano Traditional DOCG, Vernaccia di S. Gimignano Riserva, Chianti Colli Senesi DOCG, San Gimignano Rosso DOC, and the Vinsanto San Gimignano DOC.
Complementing the tasting, the winery also offers high-quality Organic Extra Virgin Olive Oil, which can be purchased at discounted prices.
With a 96% recommendation rate and an average rating of 4.8 stars, the San Quirico Winery’s Gourmet Wine Tour is an excellent choice for those looking to enjoy the rich wine culture of San Gimignano.
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Frantoio Di San Gimignano: Oil Mill Tour and Tasting
The Frantoio di San Gimignano oil mill offers visitors an immersive tour and tasting experience, providing a glimpse into the ancient traditions and technological progress of olive oil production in the region.
The 1.5-hour tour, available in English and Italian, features multimedia displays, interactive panels, and virtual reality stations. Guests can explore the mill’s olive oil production process and learn about the history and evolution of the industry.
The highlight of the visit is the olive oil tasting, where visitors can sample the mill’s extra virgin olive oil accompanied by typical regional bread and a technical explanation of the product’s properties.
The tasting experience aims to elevate the visit and engage the palate. The mill also offers a range of products for purchase, including olive oils, traditional sauces, preserves, and cosmetics.
While reviews are mixed, with some appreciating the multimedia aspects and others expecting more guided interaction, the positive feedback on the tasting experience and learning about local products suggests a worthwhile visit for those interested in the regional olive oil heritage.
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Private Tour: San Gimignano Walking Tour
Visitors can embark on a captivating private walking tour of the UNESCO World Heritage site of San Gimignano. This customizable tour allows groups of up to 15 people to explore the town’s medieval landmarks and picturesque Tuscan countryside.
Departing from the main entrance, Porta San Giovanni, the tour starts along the Francigena pilgrimage road, passing a 12th-century pilgrim shelter.
Along the way, travelers will enjoy panoramic views of vineyards, olive groves, and cypress trees. The tour then focuses on the central plaza, visiting the Romanesque cathedral, the Torre Grossa, and the Sant’Agostino church.
Guests can also choose to see optional sites like Gothic frescoes and medieval towers. At the end, the tour concludes in the heart of San Gimignano, where the guide provides recommendations for dining and further exploration.
With a 5-star rating and 100% traveler recommendation, this private walking tour offers an informative and enjoyable experience led by knowledgeable local guides.
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San Gimignano: Mini Wine Tour With Tuscan Aperitif
A 2-hour mini wine tour with a Tuscan aperitif allows visitors to savor the flavors of San Gimignano’s renowned wineries. Guests are introduced to the region’s rich winemaking heritage as they explore local cellars and sample a selection of the area’s finest vintages.
The tour culminates with a traditional Tuscan aperitif, where participants can enjoy a selection of local cheeses, cured meats, and other delectable bites paired with the region’s signature wines.
Throughout the experience, knowledgeable guides share insights into the unique terroir, grape varieties, and production methods that contribute to the distinctive character of San Gimignano’s wines. Participants have the opportunity to engage in lively discussions, ask questions, and gain a deeper appreciation for the art of winemaking in this historic Tuscan town.
The mini wine tour provides a perfect complement to the area’s stunning medieval architecture and scenic landscapes, offering a well-rounded cultural and culinary experience.
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Chianti and Castle Small Group Tour From San Gimignano
Although a full-day small-group wine tour in Tuscany’s Chianti region, this excursion promises an immersive exploration of the area’s renowned wineries and historic landscapes.
Visitors will have the chance to visit two esteemed wineries, Castellina In Chianti and Fattoria Lornano, where they’ll enjoy two wine tastings paired with traditional Tuscan snacks. The tour includes transportation from San Gimignano in an air-conditioned minivan or minibus, ensuring a comfortable and personalized experience for a maximum of 8 participants.
Along With the wine tastings, the tour also offers an olive oil and balsamic vinegar sampling, as well as the opportunity to savor local products like bread and salami.
Knowledgeable multilingual guides will lead the way, providing insights into the region’s winemaking traditions and cultural heritage. With gratuities included, this tour offers excellent value for money, starting from $90.68 per person.
Though some past guests have noted minor scheduling issues, the overall feedback is positive, with praise for the tour guide’s expertise, the stunning scenery, and the memorable winery visits.
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San Gimignano: Premium Wine Tour With Lunch
If you’re seeking a premium wine tour that offers an immersive glimpse into San Gimignano‘s renowned viniculture, the “San Gimignano: Premium Wine Tour With Lunch” is an exceptional choice.
This tour takes you to two renowned wineries, where you’ll enjoy tastings of the region’s celebrated Vernaccia di San Gimignano and other local varietals.
During the tour, you’ll learn about the winemaking process from expert vintners and discover the unique terroir that gives these wines their distinctive character.
The highlight of the experience is a delectable lunch at one of the wineries, featuring regional specialties expertly paired with the wines you’ve sampled.
With a small group size, you’ll enjoy a personalized experience and have ample opportunities to ask questions and engage with the knowledgeable guides.
Whether you’re a wine enthusiast or simply seeking to learn about the rich cultural heritage of San Gimignano, this premium wine tour is a must-do activity during your visit.
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San Gimignano Family Farm Tour With Wine and Olive Oil Tasting
Enjoy the rich agricultural heritage of San Gimignano with the captivating “San Gimignano Family Farm Tour With Wine and Olive Oil Tasting.”
This private experience offers an intimate glimpse into the daily workings of a local farming family, where you’ll discover the secrets behind the region’s renowned wines and olive oils.
Guided by the farming family, you’ll stroll through picturesque vineyards and olive groves, learning about their sustainable practices.
Indulge in a tasting of four organic wines, alongside artisanal Tuscan pecorino cheeses and bruschetta.
Savor the robust flavors of the family’s award-winning extra virgin olive oil, complemented by freshly baked bread.
With a 93% traveler recommendation and an average rating of 4.7 out of 5, this tour promises an authentic and memorable experience.
Whether you’re a wine enthusiast or simply curious about Italian culinary traditions, this family farm tour isn’t to be missed during your visit to San Gimignano.
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From Florence: San Gimignano Winery Tour With Wine Tasting
This captivating half-day tour from Florence takes visitors to the renowned Tenuta Torciano winery in the picturesque town of San Gimignano. Priced from $84.89 per person, the 4-hour tour includes pickup and drop-off from the Florence city center, as well as a free cancellation policy up to 2 days in advance.
At the winery, guests will meet the winemaker and explore the vineyards and cellars, learning about the winemaking process and different Tuscan wines. A guided tour led by a charismatic wine expert provides an immersive experience.
The highlight is a tasting of 4 Tuscan wines and extra virgin olive oil, accompanied by local snacks such as cheese, bread, and cured meats.
Visitors can take in the scenic beauty of the surrounding gardens and woods, and enjoy a viewpoint overlooking the rolling hills of San Gimignano and Tuscany.
With an English and Italian speaking host, this tour caters to dietary requirements and offers the opportunity to purchase wines, oils, and balsamic vinegar for home delivery.
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San Gimignano Guided Tour Review
Although San Gimignano‘s picturesque medieval towers and charming town center are a major draw for visitors, a guided tour can elevate the experience by providing valuable historical context and insider knowledge.
The San Gimignano Guided Tour offers just that, led by authorized guides who share their expertise on this UNESCO World Heritage site. Starting at 11 am in Piazza Duomo, the tour accommodates up to 20 travelers and promises a comprehensive exploration of the town’s highlights, with the option to return to the meeting point upon completion.
Priced at $21.34 per person, the tour provides excellent value, with a Lowest Price Guarantee and flexible cancellation policy. Accessibility features, including wheelchair and stroller access, make the tour inclusive.
While some reviewers suggest issues with bilingual tours, the guides’ ability to provide insights in both English and Italian is generally praised.
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San Gimignano: Winery Tour With Wine Tasting and Lunch
For those seeking to savor the renowned wines of the Tuscan region, the San Gimignano: Winery Tour With Wine Tasting and Lunch promises an immersive experience.
Priced at $7326 per person, this 2-hour tour offers a comprehensive wine and food adventure. Guests will enjoy a tasting of 5 wines, along with a Tuscan-inspired lunch featuring local products, cold cuts, cheeses, and even a grappa tasting.
The guided tour provides an in-depth look at the winemaking process, with visits to the cellar and vineyards. The tour accommodates small groups, ensuring a personalized experience.
Accessibility is also a consideration, as the tour is wheelchair-friendly. Prospective guests can take advantage of the flexible cancellation policy, with full refunds available up to 24 hours in advance.
With an impressive 4.8/5 rating based on 8 reviews, this tour is sure to delight wine enthusiasts seeking an authentic Tuscan experience.
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Private Walking Tour in San Gimignano With a Local Licensed Guide
Travelers seeking an immersive exploration of San Gimignano’s iconic landmarks will find the Private Walking Tour in San Gimignano With a Local Licensed Guide to be an excellent choice. This personalized tour covers the town’s main attractions, including the Bell Tower, 13th-century Church of Sant’Agostino, Duomo, and Cisterna squares.
The tour is ideal for first-time visitors and can be tailored to individual tastes and schedules, ensuring a truly bespoke experience.
Led by a knowledgeable local guide, the tour provides a rundown of San Gimignano’s rich history and architecture. Travelers will benefit from the guide’s expertise and engage in an informative and interactive experience.
The tour is wheelchair and stroller accessible, making it suitable for a wide range of participants. With positive reviews highlighting the guide’s friendly demeanor and the tour’s intimate and personalized nature, this private walking tour offers an excellent opportunity to discover the hidden gems and less-touristy areas of this picturesque Tuscan town.
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San Gimignano Wine Tour From Florence Top Rated Free Shuttle
Those seeking a comprehensive wine experience can consider the San Gimignano Wine Tour from Florence. Priced from €89.00 per person, this 4-hour activity takes visitors to an authentic Tuscan winery established in 1720.
The tour includes a guided exploration of the vineyards and cellars, followed by a tasting of four different Tuscan wines accompanied by local snacks.
The tour also features a scenic viewpoint stop to observe the iconic San Gimignano skyline and Tuscan hills.
Transportation is provided, with a free shuttle service from Florence city center to the Tenuta Torciano Winery and back.
While weather-related changes may occur, the tour is designed to be flexible, with the opportunity to purchase wines, oils, and balsamic vinegar directly from the producer.
Dietary requirements can be accommodated if communicated during booking.
With personal assistance from the Torciano staff and insights into the winemaking process, this tour offers a memorable and immersive Tuscan wine experience.
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Private Tour in San Gimignano
Visitors seeking a personalized exploration of San Gimignano, the UNESCO-listed medieval gem, can embark on a private walking tour. The 2-hour experience offers a guided discovery of the historic center, renowned for its Etruscan history and well-preserved architecture.
With a local guide leading the way, travelers won’t miss any of the town’s top attractions, from the iconic Civic Museum and Cathedral to the medieval towers that dot the skyline.
Throughout the tour, guests can enjoy the charming ambiance, stopping to sample local delicacies like wine and gelato.
The experience is accessible for all, with wheelchair and stroller accommodations available upon request. Comfortable attire and a moderate fitness level are recommended, as the tour involves walking medium distances.
With a 5.0 rating and 100% recommendation from previous travelers, this private tour promises an engaging and memorable introduction to the enchanting town of San Gimignano.
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Florence: Wine Tasting and Paring Class Guided Tour
Although located in the heart of Florence, the Wine Tasting and Pairing Class Guided Tour transports participants to the picturesque Tuscan countryside.
This 1.5-hour experience allows guests to sample a selection of Tuscan wines, including Chianti Classico, Chianti Classico Reserve, Tuscan Prosecco, and White Wine. Accompanied by a platter of traditional Tuscan appetizers, the tasting is led by expert guides who provide insights into local wine production and history.
Priced from £38.65 per person, the tour caters to both amateurs and experts, with options for 3 or 7 wine varieties.
Wheelchair-accessible and with dietary requests accommodated, the experience receives an impressive 4.9/5 rating from past participants.
With free cancellation up to 24 hours in advance, the Wine Tasting and Pairing Class Guided Tour offers a convenient and highly-rated way to take in the flavors of Tuscany, right in the heart of Florence.
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Chianti E-Bike Tour From Florence With Wine Tasting
Setting out on a Chianti e-bike tour from Florence, travelers can explore the picturesque landscapes of San Gimignano while indulging in a wine tasting experience. This private tour offers a personalized adventure, with only your group participating.
Setting off at 9:00 am, you’ll have the opportunity to pedal through the rolling hills and vineyards of the Chianti region.
The tour includes the use of a bicycle and helmet, as well as air-conditioned transportation. Enjoy a delectable Tuscan lunch featuring local delicacies like cold-cuts, pecorino cheese, and bruschetta. Bottled water and gratuities are also provided.
The meeting point is at the COOP supermarket in San Donato, and the tour returns to the same location.
Though not recommended for those with physical limitations, this moderate-intensity tour promises breathtaking views and a chance to savor the flavors of the Chianti countryside.
With exceptional reviews and a free cancellation policy, this e-bike adventure is an excellent way to experience the best of San Gimignano.
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Brunello Di Montalcino Wine Tour From San Gimignano
Seeking to explore the renowned Brunello di Montalcino wines, travelers can embark on a guided wine tour from the charming town of San Gimignano. The 6.5-hour “Brunello di Montalcino Wine Tour” offers an immersive experience, including visits to two renowned wineries, wine tastings, and local snacks, all for a starting price of $109 per person.
The tour starts from Porta San Giovanni in Siena and accommodates a maximum of 8 people, with tour guides fluent in Italian, English, and Spanish. While pickup and drop-off services are available for an additional fee, the tour itself includes air-conditioned transportation and expert multilingual escorts.
Highlights of the itinerary include exploring the medieval town of Montalcino and its historic fortress, enjoying scenic photo stops, and experiencing free time to wander the charming streets.
Customer reviews generally praise the friendly guides and beautiful scenery, though some note limited wine tastings and lack of food options. Nonetheless, this tour provides an opportunity to explore the world-class Brunello di Montalcino wines in the heart of Tuscany.
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San Gimignano Wine Tour and Tuscan Appetizer for Small Group
Travelers seeking an immersive introduction to Tuscany’s renowned viticulture can join the “San Gimignano Wine Tour and Tuscan Appetizer for Small Group” experience.
Located in the picturesque town of San Gimignano, this 5-star rated tour offers a delightful blend of wine tasting and traditional Tuscan appetizers.
The experience begins with a starter of Tuscan appetizers, including pecorino cheeses, Tuscan salami, bruschetta, and olive oil, accompanied by wine tasting. Guests can then savor the flavors of the region with a dessert of cantuccini biscuits and dessert wine.
Included in the tour are private transportation, a wine and oil tasting, and a lunch.
The meeting point is easily accessible, with the tour being wheelchair and stroller friendly, as well as welcoming service animals.
With a maximum of 300 travelers, this small-group experience provides an intimate and personalized exploration of San Gimignano’s renowned winemaking heritage.
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Chianti and San Giminiano Wine Tour – Private Experience
For those looking to explore the rich wine heritage of Chianti and San Gimignano, the “Chianti and San Giminiano Wine Tour – Private Experience” offers an unparalleled opportunity.
This private tour whisks you away to the picturesque Tuscan countryside, where you’ll visit renowned wineries and savor the finest local vintages.
Your journey begins with a visit to a Chianti winery, where you’ll learn about the region’s acclaimed winemaking traditions. Indulge in tastings of the region’s signature Chianti Classico, exploring its complex flavors and aromas.
Next, you’ll venture to the charming medieval town of San Gimignano, known for its striking skyline of historic towers. Here, you’ll visit a family-owned winery and sample the renowned Vernaccia di San Gimignano, a white wine that has been produced in the area for centuries.
Throughout the tour, you’ll have the opportunity to savor local delicacies and gain insights into the rich culinary heritage of Tuscany.
This private experience ensures a personalized and immersive journey into the heart of the region’s wine culture.
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Private Vintage Fiat 500 Tour in Chianti From San Gimignano
Imagine traversing the picturesque Chianti region in a classic Fiat 500, enjoying the essence of Tuscan charm. This private tour from San Gimignano offers an unforgettable experience, complete with a professional guide, wine-tasting, and a delightful lunch.
Departing from Porta San Giovanni, you’ll have the option of arranging a pickup, ensuring a seamless start to your adventure. The tour, which runs from 9:30 am, promises a day filled with the best of Chianti’s sights and flavors.
While the tour isn’t wheelchair accessible, it’s suitable for most travelers, and a vegetarian option is available. Service animals are welcome, and you’ll need a valid driver’s license to take the wheel of the vintage Fiat.
Cancellation is free up to 24 hours before the experience, and you can reserve your spot now and pay later for added flexibility.
Don’t miss the opportunity to explore Chianti’s enchanting landscapes and savor its renowned wines in the comfort of a classic Fiat 500.
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Private Guided Tour in San Gimignano
Set out on a captivating private guided tour through the enchanting medieval town of San Gimignano. Priced at $144.10 per person, this 2-hour walking experience takes you on a journey through the town’s historical landmarks, including the Cistern Piazza, Civic Museum, Montestaffoli Fortress, and Piazza Duomo.
Along the way, you’ll learn about the local legends and noble families that have shaped San Gimignano’s past. The tour offers the option to visit the Rocca di Montestaffoli and the interior of the Cathedral, as well as the opportunity to indulge in award-winning ice cream and local DOCG white wine.
Led by a live, knowledgeable guide available in English and Italian, this private group experience ensures a personalized and engaging exploration of the town. Headphones are provided for larger groups at an additional cost.
With free cancellation up to 24 hours in advance and a “reserve now, pay later” option, this tour is a flexible and hassle-free way to discover the enchanting San Gimignano.
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From San Gimignano: Half-Day Chianti Wine Tour
Departing from San Gimignano, this half-day Chianti wine tour offers an immersive exploration of the renowned Chianti wine region. Priced from $94.32 per person, the 5.5-hour experience includes roundtrip transportation, a guided tour led by a local expert, and tastings of up to 9 different wines, including Chianti Classico DOCG and Super Tuscan varieties.
Participants will first visit the Tuscany Wine Tasting School for an educational wine tasting lesson, followed by a guided tour and tasting at a local winery. The tour also includes a brief stop in the picturesque town of San Gimignano.
Along With the wine tastings, the experience features samplings of extra virgin olive oil and balsamic vinegar. Snacks and lunch are provided.
This Chianti wine tour isn’t suitable for pregnant women or children under 18. A minimum of 4 participants is required, with a maximum group size of 60.
Cancelations can be made up to 24 hours in advance for a full refund. The tour operates rain or shine.
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Sum Up
San Gimignano offers a range of fantastic tour options for wine enthusiasts and sightseers alike. From winery visits and tastings to horseback riding and vintage car excursions, there’s something to suit every interest. Whether you’re looking to explore the region’s renowned vineyards or discover the historic town’s charming streets, these tours provide an unforgettable way to experience the best of San Gimignano.