Top San Gimignano Wine Tasting Tours

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.

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.

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!

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.

A few steps from San Gimignano, there is a splendid family-run winery. Here you can taste the typical Tuscan products: starting from the wine up to tasty local croutons. You will visit the cellar, the vineyards, and all the places where the wine comes to life. You will listen to stories, and curiosities, and you will learn the winemaking processes that make Tuscany and Chianti areas to be protected and loved. You will discover the secrets of wine and grapes and the best combinations with strictly typical foods. Do not miss the opportunity to combine Tuscan wine with appetizing foods (such as cheese and ham) and find out how wines are produced in a real cellar. You can have a lovely tasting of 4 wines accompanied by snacks of typical products preceded by a tour of cellars and vines.

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, tastings of four estate-made wines, and extra virgin olive oil.

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.

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.

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.

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.

Enjoy a half-day journey from San Gimignano to the picturesque wine region of Chianti. Begin your adventure with a visit to the charming village of Castellina in Chianti, followed by a delightful wine tasting at a nearby vineyard. Stroll around Monteriggioni, a medieval village where you can admire the ancient walls. At a beautiful wine estate, take part in a wine tasting savoring the rich aroma and ruby-red tones of Chianti wine crafted from Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes.

A relaxed Tuscan light lunch just steps from San Gimignano’s historic center. A moment to slow down, sit, and enjoy a balanced combination of wine and traditional flavors in an authentic and welcoming setting. What makes it special: Easy and enjoyable light lunch experience in the heart of Tuscany Guided tasting of 5 wines, from sparkling to Chianti and Supertuscan Selection of olive oils and balsamic vinegars Traditional Tuscan appetizers with cured meats, cheeses, and bruschetta Homemade lasagna as a warm first course Dessert with Vin Santo to complete the experience Perfect for a midday break that combines taste, simplicity, and the true spirit of Tuscan hospitality.

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.

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.

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.

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.

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.

This tour is not a simple wine tasting, but you will have the opportunity to be accompanied by the producer in the vineyards and in the cellar, to get to know the viticulture and winemaking techniques

Tuscany is Italy’s gastronomic heart and this full-day tour from San Gimignano is the ideal introduction for traveling foodies. Sample regional wines and Tuscan specialties at a Montalcino winery; enjoy a self-guided tour of Montalcino fortress; taste regional delicacies such as Pecorino cheese in Pienza; and discover the famous Nobile di Montepulciano wine at a Montepulciano winery.

Step into the Middle Ages on this 2-hour private tour of San Gimignano, one of Italy’s most stunning medieval villages. Stroll through historic squares, admire ancient towers, and choose to visit the majestic Cathedral or climb the Big Tower for breathtaking views. Discover local traditions, art, and flavors, including award-winning gelato and DOCG Vernaccia wine.

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.

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.

Casale Terzo is a historic rural building that bears witness to an important past and a destiny that united two organic wine families. A corner of paradise in Val d’Elsa, framed by places such as the towers of San Gimignano, the fortress of Casole d’Elsa, in a territory that embodies the most typical form of the Tuscan landscape. You are at the center of a beauty universally recognized and famous for the renowned wine tradition, where the colors of the sunset become those of the heart. You will taste the local wines of our production and the olive oil, all of which are produced by us. In the meantime, you will enjoy your Tuscan landscape.