The 15 best things to do in San Gimignano (2026)

The ranked list

1. 

   1. Wine and food tasting in an organic family winery

   Outty Ranking94

   Guided tour of our winery estate near San Gimignano: vegetable garden, orchard, vineyard, olive grove, Vin Santo aging room (vinsantaia), historic cellar, and a collection of traditional tools from farming world. Tastin. 90+ Club at 94/100, 5.0/5 from 188 traveler reviews, 2.8h from $93, free cancellation, an Outty 90+ Club member.

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2. 

   2. Tuscan Cooking Class

   Outty Ranking91

   I'm Katia and me and my uncle Fulvio run the Tuscan cooking class in our family farmhouse. We are 4 km far from the fantastic town of San Gimignano and we teach you how to prepare a real Tuscany meal but most important w. 90+ Club at 91/100, 5.0/5 from 653 traveler reviews, 3h from $151, free cancellation, an Outty 90+ Club member.

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3. 

   3. Wine Tour with Lunch and Wine Tasting

   Outty Ranking84

   It is an authentic experience of a family vineyard where you can understand the wine making process, enjoying the final products. An interesting visit of our small family vineyard with history about the property and gra. Exceptional at 84/100, 4.9/5 from 87 traveler reviews, 2.5h from $75, free cancellation.

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4. 

   4. Tuscany Horseback Riding and Winery Tour with Lunch

   Outty Ranking83

   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. Exceptional at 83/100, 5.0/5 from 39 traveler reviews, 7h from $139, free cancellation.

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5. 

   5. Cesani Wine Experience

   Outty Ranking83

   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 c. Exceptional at 83/100, 4.9/5 from 52 traveler reviews, 1.5h from $44, free cancellation.

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6. 

   6. San Gimignano Wine Tasting & Tuscan Dinner at a Local Winery

   Outty Ranking83

   Your journey begins with a relaxed drive from San Gimignano to a charming winery nestled among the rolling hills of Chianti. Upon arrival, you’ll be greeted with a welcome drink before setting off on a guided tour of the. Exceptional at 83/100, 4.5/5 from 203 traveler reviews, 4h from $70, free cancellation.

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7. 

   7. Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano

   Outty Ranking83

   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 th. Exceptional at 83/100, 4.8/5 from 76 traveler reviews, 6h from $87, free cancellation.

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8. 

   8. 5 Wine Tastings in San Gimignano

   Outty Ranking78

   Full immersion in the world of wine. The experience is created for those who want to get closer to the Tuscan tradition of producing of Vernaccia di San Gimignano and Chianti Colli Senesi. The itinerary consists of a com. Strongly Recommended at 78/100, 4.9/5 from 49 traveler reviews, 2h from $75, free cancellation.

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9. 

   9. Private Wine & Oil Tasting with Lunch

   Outty Ranking76

   Treat yourself with a delightful Tuscan experience. Dive into the green shades of our vineyard with a private description of our farm. The experience will start with a detailed introduction to the agricultural methods we. Strongly Recommended at 76/100, 4.6/5 from 119 traveler reviews, 1.5h from $79, free cancellation.

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10. 

    10. Private Tour in San Gimignano

    Outty Ranking76

    Immerse yourself in the Middle Ages, visiting one of the most beautiful medieval villages of Italy. You will never forget the ancient towers and the dreamlike landscape by which it is surrounded. The tour will begin from. Strongly Recommended at 76/100, 4.9/5 from 60 traveler reviews, 2h from $162, free cancellation.

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11. 

    11. Organic Wine Tour&Tasting overlooking Chianti Classico Vineyards

    Outty Ranking76

    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 "Zer. Strongly Recommended at 76/100, 4.8/5 from 34 traveler reviews, 1.3h from $41, free cancellation.

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12. 

    12. Our Chefs' cooking experience refines your cooking skills.

    Outty Ranking76

    More than a Cooking Class Cooking Class includes: - an intensive cooking session with instruction (in English) and practice with our chef, 3 course meal following the lesson including selected wines (Prosecco and Chianti. Strongly Recommended at 76/100, 5.0/5 from 25 traveler reviews, 4h from $162, free cancellation.

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13. 

    13. Private Tuscan meal with Wine and EVO oil tasting

    Outty Ranking75

    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. Strongly Recommended at 75/100, 4.8/5 from 46 traveler reviews, 1.5h from $79, free cancellation.

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14. 

    14. Truffle Lunch & Hunting Experience in San Gimignano

    Outty Ranking73

    Join an authentic truffle hunting and experience the thrill of finding, smelling, and touching one of nature’s rarest treasures. Led by expert truffle hunters Mirco and Luca and their highly trained dogs, you’ll explore. Strongly Recommended at 73/100, 4.9/5 from 44 traveler reviews, 3h from $226, free cancellation.

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15. 

    15. Family-Friendly Tuscany Day Tour for Wine Lovers and Non-Drinkers

    Outty Ranking73

    Discover the authentic flavors of Tuscany on our Family-Friendly Tuscany Tour — a perfect mix of food, wine, and fun for all ages! Travel through the scenic Chianti countryside and visit a local farm overlooking San Gimi. Strongly Recommended at 73/100, 4.9/5 from 16 traveler reviews, 7h from $185, free cancellation.

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Traveler ratings are provided by Viator and Tripadvisor. The Outty Ranking is our own independent evaluation. How the ranking works.

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