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San Gimignano is surrounded by quiet countryside dotted with small wine estates. Visit one of these traditional farms and connect with local hosts on this tour and wine tasting experience. Take in the organic farm's garden, orchard, vineyard, olive grove, "vinsantaia" aging room, and cellar. Then enjoy a tasting of eight organic wines of your choice paired with the farm's own olive oil plus local cheeses and cold cuts and other culinary combinations.
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Wine and food tasting in an organic family winery
2 hours 45 minutes
Free Cancellation
5.0
(176)
from
$93
A sunset dinner with panoramic views over San Gimignano. As golden light falls over the medieval towers, the terrace becomes an intimate setting where wine, cuisine, and landscape come together. What makes it special: Exclusive panoramic terrace at sunset overlooking San Gimignano Guided tasting of 8 wines, including Chianti Classico Riserva and Supertuscan Selection of premium olive oils and balsamic vinegars Full Tuscan dinner with appetizers, homemade lasagna, and a traditional meat course Dessert with Vin Santo to conclude the experience A refined and atmospheric evening, perfect for those who want to experience Tuscany at its most scenic and authentic moment.
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San Gimignano Sunset Belvedere Dinner and Wine Tasting
2 hours 15 minutes
Free Cancellation
5.0
(3)
from
$73
Escape the crowds of San Gimignano by visiting a small family-run estate just outside of town. During this experience, you'll learn all about the winery and its history, as well as its grape varietals, olive orchards, and wine cellar visit. You'll enjoy a delicious lunch prepared with local products and a tasting of four different wines, each produced at the estate.
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Wine Tour with Lunch and Wine Tasting
2 hours 30 minutes
Free Cancellation
4.9
(77)
from
$76
Wine tasting in Tuscany might seem overwhelming when you don’t know where to start. But, this San Gimignano wine experience makes it easy, with a prebooked tasting session of up to five local wines, paired with local snacks. As well as a tasting, you’ll tour the vineyard and cellars, learning about the local vernaccia white wine grape and the Chianti Colli Senesi area that produces some of the region’s most esteemed wine.
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5 Wine Tastings in San Gimignano
2 hours
Free Cancellation
4.9
(46)
from
$76
Combine your San Gimignano sightseeing with a taste of the local terroir on this organic winery visit. Go behind-the-scenes at the family-run farm and vineyard, tour the facilities, and then indulge in a generous wine tasting. You’ll also sample locally made olive oils and balsamic vinegars, and enjoy a classic Tuscan feast of bruschetta, pasta, and more.
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Private Wine & Oil Tasting with Lunch
1 hour 30 minutes
Free Cancellation
4.6
(117)
from
$79
Discover the charm of San Gimignano on this private culinary experience. Guided by a family member who shares stories and insights into their sustainable craft, you'll taste and learn about this special region. Then, savor a private tasting featuring organic wines, premium extra virgin olive oils, and a freshly prepared farm-to-table meal. It's the perfect way to immerse yourself in the flavors and traditions of Tuscany.
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Private Wine & Evo Oil Tasting with Tuscan Meal
1 hour 30 minutes
Free Cancellation
4.9
(20)
from
$79
Explore Tuscany beyond the center of San Gimignano with this vineyard visit. Travel to a family-run organic farm where grapes and olives are grown. Sample the vineyard’s wines and extra virgin olive oil alongside a vegetarian meal including bruschetta, pasta with vegetables, and a selection of pecorino cheeses. A traditional dessert and dessert wine are included.
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Private wine & Evo Oils Tasting with Vegetarian Meal
1 hour 30 minutes to 2 hours
Free Cancellation
5.0
(2)
from
$79
The experience will begin with the meeting of guests at our winery. Our dedicated staff will welcome you at our cellar, illustrating what you have chosen. The tasting will begin with a brief introduction on the family history and the presentation of the company, and then continue inside our tasting room called "barriccaia", where you can taste the products of your choice, included in the tasting package purchased.
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Wine Tasting "San Gimignano"
1 hour
Free Cancellation
4.0
(3)
from
$41
Experience the flavors of Tuscany during a visit to a family-run farm and winery in San Gimignano. See where grapes and olives are cultivated organically and go for a stroll through the vineyard and olive groves. Taste wines and extra virgin olive oil produced on-site alongside a Tuscan meal with several dishes including saffron, a local product.
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Private Wine & Evo Oil Tasting with Saffron Meal
1 hour 30 minutes
Free Cancellation
4.6
(5)
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$87
Experience the authentic flavors of Tuscany with a guided winery tour and tasting in a stunning San Gimignano vineyard. Sample five premium Tuscan wines paired with bruschetta drizzled in estate-produced olive oil. Families are welcome—while adults enjoy the tasting, kids can visit friendly farm animals, sip fresh juices, and unleash their creativity in the interactive “Paint Your Own Wine Label” activity. A perfect blend of culture, flavor, and fun for all ages!
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Tuscan Wine & Bruschetta Tasting for Families in San Gimignano
2 hours
Free Cancellation
5.0
(1)
from
$45
Discover Tuscany from a truly unique perspective with this small-group horseback riding experience through rolling vineyards and olive groves, followed by a traditional lunch and wine tasting at a local estate. Departing from Florence or San Gimignano, this experience offers the perfect balance of scenic adventure and authentic flavors, allowing you to explore the countryside away from the crowds and savor regional specialties paired with estate-produced wines. Ideal for nature lovers and food enthusiasts alike, it’s an unforgettable way to immerse yourself in the beauty, tastes, and traditions of Tuscany, all in one day.
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Tuscany Horseback Riding and Winery Tour with Lunch
7 hours
Free Cancellation
5.0
(23)
from
$126
100% Organic & Family-Run: You won't find a corporate atmosphere here. We are a real working farm, and we share the same passion for sustainability that we put into every bottle of our organic Chianti Classico. The "Zero-Meter" Connection: Our tasting terrace overlooks the exact vines your wine came from. You can trace the entire journey of the grape—from the soil beneath your feet to the glass in your hand. Small-Scale Intimacy: We prioritize quality over quantity. Our groups are kept small to ensure you have plenty of time to ask questions, savour, and truly soak in the silence and colors of the Chianti countryside.
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Organic Wine Tour&Tasting overlooking Chianti Classico Vineyards
1 hour 15 minutes
Free Cancellation
4.7
(21)
from
$41
Get ready for a truffle-tasting adventure with this 3-hour lunch and hunting experience in San Gimignano. Your certified guides will take you to the prime truffle grounds and teach you everything you need to know about these esteemed delicacies. With your four-legged friends leading the way, you can experience the thrill of hunting for truffles in the midst of nature. Return to Podere La Marronaia for a mouth-watering truffle lunch, perfectly paired with organic wines and olive oils.
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Truffle Lunch & Hunting Experience in San Gimignano
3 hours
Free Cancellation
4.9
(41)
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$227
The Cesani family and our staff are pleased to welcome you to Pancole, just 5km from the historic center of San Gimignano, where you will have the opportunity to sit down and taste the company's products presented with competence and passion, and thus have the opportunity to know the history, the production process and the organoleptic characteristics of all the products that the Cesani family offers. The tasting includes 5 wines of our production (2 Vernaccia di San Gimignano, 3 Red Wines) and our extra-virgin olive oil. The type of wines offered may vary according to availability. A taste of pecorino and other traditional goodies will accompany the wine presented. The guided tour of the modern and rational company cellar will allow you to discover that tradition and technology are an inseparable combination for the production of great wines from organic grapes. Simplicity and professionalism are fundamental characteristics for obtaining products of the highest quality.
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Cesani Wine Experience
1 hour 30 minutes
Free Cancellation
4.9
(50)
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$44
A special tour that gives more space to the natural environments surrounding the farm. You will be taken on a walk through the fields and vineyards and linger in the shade of a large oak tree for a cool Aperitivo. The tour continues through the vinsantaia, historical cellar, collection of agricultural tools. Tasting of 8 wines from our production: - "Casa Lucii" DOCG Vernaccia di San Gimignano; - 2 different vintages of "Mareterra" DOCG Vernaccia di San Gimignano reserve; - "Spicchio" IGT rosé Tuscan; - "Fuscelli" DOCG Chianti; - "Senarum" DOCG Chianti Colli Senesi; - "Arturo" IGT Tuscan Red with tailor-made artisanal chocolate pralines; - "Curato" DOC Vin Santo del Chianti with Tuscan Cantuccini. The tasting is accompanied by a taste of our organic extra virgin olive oil, cheese and cold cuts selection produced by local farms and accompanied by vegetables from the garden.
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Tasting with welcome Aperitivo in the vineyard of organic wines
4 hours
Free Cancellation
5.0
(2)
from
$140
Learn how to make authentic homemade pasta and prepare your own lunch. Discover secrets and techniques of local traditional cuisine. All the dishes will be accompained by the wines of our production.
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"Hands in dough" Cooking Class with Lunch
2 hours 30 minutes
Free Cancellation
5.0
(2)
from
$128
Escape to the heart of Tuscany with a private vineyard experience in San Gimignano. Discover the secrets of biodynamic winemaking and olive oil production at a historic family-run farm. Enjoy a guided tasting of organic wines, extra virgin olive oils, and balsamic vinegar, paired with a delicious farm-to-table Tuscan meal.
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Private Tuscan meal with Wine and EVO oil tasting
1 hour 30 minutes
Free Cancellation
4.8
(46)
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$79
Escape to a charming family-run farm near San Gimignano and immerse yourself in the authentic flavors of Tuscany. Surrounded by vineyards, olive groves, and stunning countryside views, this experience offers the perfect blend of relaxation, tradition, and sustainability. Begin with an introduction to biodynamic farming, learning about the passion and eco-friendly practices behind our organic wines and extra virgin olive oils. Then, settle into a rustic Tuscan house overlooking rolling hills and enjoy a guided tasting of our handcrafted wines and olive oils.
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Private Wine and Extra Virgin Olive Oil Tasting
45 minutes
Free Cancellation
4.8
(23)
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$49
Visit two Tuscan wineries without having to worry about designating a driver by opting for this tour that includes transportation. Immerse yourself in the Chianti wine region as you sample a variety of wines. Discover the art of winemaking through tastings while enjoying the scenery of the Tuscan countryside. Then head to San Gimignano to spend some time exploring its medieval ramparts.
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Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano
6 hours
Free Cancellation
4.8
(70)
from
$94
If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia vineyard, it provides a deep connection to the land, traditions, and flavors of Tuscany. You’ll start with an insightful introduction to our biodynamic winemaking and olive oil production, learning the passion behind every bottle. Then, enjoy a private wine, extra virgin olive oil & balsamic vinegar tasting, paired with a delicious Tuscan lunch or dinner, all while admiring the stunning views of San Gimignano’s famous towers. What makes this experience special? - A private setting in one of San Gimignano’s oldest Vernaccia vineyards - A guided tasting of organic wines and extra virgin olive oils - A farm-to-table Tuscan meal prepared with fresh, seasonal ingredients - A cozy yet elegant atmosphere, perfect for relaxation - An unforgettable journey into the heart of Tuscan flavors and traditions.
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Private Wine, Evo Oil, Balsamic Vinegar Experience & Meal
1 hour 30 minutes
Free Cancellation
4.8
(16)
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$79
Skip the busy cooking classes and instead opt for a private culinary immersion in San Gimignano. At a local’s home, benefit from the undivided attention of your instructor as you learn to prepare three traditional dishes, before dining with the family. Few travelers get the opportunity to enjoy such an intimate experience.
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Authentic Tuscan Cooking Class & Winery Tour in San Gimignano
3 hours
Free Cancellation
5.0
(5)
from
$185
Soak up the local vino and small-town charm of San Gimignano on this wine tasting trip from Siena. Explore San Gimignano first at your leisure, spotting landmarks such as the Collegiata and Pizza del Duomo while strolling the medieval streets. Afterward, travel deeper into the Tuscan hills, and enjoy an intimate winery tour. Sip and swirl Chianti blends with an inside look at the winemaking process.
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San Gimignano Wine Tasting & Tuscan Dinner at a Local Winery
4 hours
Free Cancellation
4.5
(203)
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$70
Special Offer
Discover the authentic beauty of Tuscany on an unforgettable scooter adventure through the famous Chianti hills. Ride along scenic roads surrounded by vineyards, olive groves, cypress trees, and medieval villages while experiencing the true essence of Tuscany. After a safety briefing and driving test, follow your local guide through panoramic routes and hidden corners of the countryside, stopping at breathtaking viewpoints and learning about Chianti wine culture and local traditions. Visit local wineries to enjoy tastings of Chianti wines, extra virgin olive oil, and balsamic vinegar. Savor a traditional Tuscan lunch in a charming vineyard setting, featuring bruschetta, cold cuts, cheeses, handmade pasta, and regional wines. Continue your scenic ride through the rolling Tuscan hills before returning to the starting point. Perfect for travelers seeking a unique blend of adventure, wine, food, and spectacular scenery.
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Chianti Scenic Drive with Wine Tastings & Tuscan Lunch
7 hours
4.5
(7,041 Operators)
from
$157
$146
Connect with a farming family just outside San Gimignano to enjoy a guided visit of the vineyards and olive groves and learn about the estate’s wine and olive oil production. Join your hosts for a private stroll through the farm, taking in views over the hills and the towers of San Gimignano. Then sample four of the farm’s own organic wines plus olive oil, served with Tuscan pecorino cheeses and bruschetta.
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Private Wine, Evo oil & Cheese Tasting
1 hour
Free Cancellation
4.7
(18)
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$58
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