Top San Gimignano Wine Tasting Tours - page 2

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.

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.

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.

Sip, swirl, and savour six delicious wines on a small-group tasting tour in San Gimignano. Learn how grapes become wine from a local expert as you enjoy paired bites and ask questions. Share tasting notes with your group and pick up insights you might otherwise miss. This one-hour tour is perfect for fitting into a busy day exploring the surrounding area of the beautiful region.

The tasting of the five wines and their combinations will be presented and served in our equipped and comfortable tasting room, where all our guests, even if spaced and safely, can enjoy a convivial and unique experience! For all those who have particular diets or intolerances, upon notice at the time of booking in the "notes" field, we are able to meet most dietary needs. The price of the tasting includes everything: tasting, water and food pairings. The structure of the Rocca di Montestaffoli does not provide bar service (coffee, tea, soft drinks, spirits, packaged foods, etc.) It is also possible to participate in the tasting with children, for them our staff will prepare a selection of gastronomic excellences at a cost of € 8 per child.Remember that by law it is forbidden to administer alcohol to minors.

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!

When you’re in Tuscany, skip the tourist plates of food and try some of the specialties for which the region is known. This private food experience takes place on a farm near San Gimignano, spotlighting balsamic vinegar, extra virgin olive oil, and wine. You’ll learn how these delicacies are produced and enjoy samples paired with a 3-course meal.

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.

An enchanting evening unfolds in an ancient cave illuminated by candlelight, where the spirit of Tuscany comes alive. Nestled within Poggio ai Laghi Enoteca Storica, this exclusive private dinner showcases authentic Tuscan flavors paired with a selection of exquisite wines, including Chianti and Supertuscans. As you savor each course—from homemade lasagna to traditional cantuccini—you’ll be immersed in the rich history of Countess Ava and her handmaidens, the inspiring figures behind this esteemed wine house. Delight in a unique culinary experience that marries elegance with tradition under the stars of San Gimignano.

See Tuscany in classic Italian style by exploring the bucolic region in a vintage Fiat 500. Take the wheel of the classic Italian automobile then ride to the stunning hilltop town of Monteriggioni, cruise through the rolling hills of Chianti, and stop at a local vineyard for a hearty lunch of local fare.

Indulge in a private truffle-based lunch in an authentic Tuscan setting at a family-run biodynamic farm near San Gimignano. Begin with an introduction to the farm’s sustainable agricultural methods, learning about biodynamic winemaking and olive oil production. Then, savor a carefully curated meal featuring truffle-infused dishes, paired with organic wines and extra virgin olive oils produced on-site.

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.

Guided small group tasting in the countryside of San Gimignano, designed for those who want to understand Tuscan wine in a simple and authentic way. The experience is conducted by a local sommelier and combines tasting of wines representative of the territory with an accessible story about vines, landscape and traditions. Ideal for those visiting San Gimignano and looking for a relaxed, convivial and cultural moment, away from standardized tastings and crowded settings.

A few steps from San Gimignano do not miss a special food and wine experience: a tasting of the best Chianti wines with lunch included and grappa tasting!

Discover the essence of Tuscany on this immersive wine tour through the beautiful Chianti region. Visit three distinct wineries, where you'll explore traditional vineyards and enjoy multiple tastings of exquisite Chianti wines. With a knowledgeable guide leading the way, you’ll learn about the art of winemaking while soaking in the stunning countryside views. Perfect for adults seeking a delightful day of wine and camaraderie.

Immerse yourself in the heart of Tuscany with a wine experience set in the scenic hills near San Gimignano. Begin with a warm welcome and an introduction to the estate, followed by a guided tour through the historic wine cellar, where traditional methods and passion come together. Enjoy a curated tasting of local wines, each paired with typical Tuscan products like cheeses, salumi, and fresh bread. The experience continues with a relaxing lunch on a panoramic terrace overlooking the vineyards. This journey offers not only authentic flavors, but also a deep connection to the land, its rhythms, and its winemaking heritage—a perfect escape for wine lovers and curious travelers alike.

San Gimignano, with its rural, hillside atmosphere, is a great place to sample Tuscan food and wine. This tour pairs Tuscan wine tasting with an elaborate Truffle-based meal at a family-run olive farm and vineyard. The meal is led by one of the farmers, who explains the characteristics of the wines and their organic production. The farm is within walking distance from the center of San Gimignano, so you can walk right over.

Immerse yourself and relax among the rows of Vernaccia di San Gimignano, tasting local products and wines: our basket will make you feel like a real Tuscan DOC.

Enjoy an authentic local experience that many travelers to Italy miss. Visit a small family vineyard to learn about the property and its grape varietals, and to visit the wine cellar. You'll learn more about Italian wines as you enjoy appetizers prepared with local products and taste three different wines produced at the estate.

An intimate Tuscan dinner experience in the heart of San Gimignano. As the day fades, the cellar becomes a quiet and atmospheric space where wine, food, and tradition come together in a refined evening setting. What makes it special: Warm and intimate evening atmosphere just steps from the historic center Guided tasting of 8 wines, including Chianti Classico Riserva, Supertuscan, and exclusive labels Selection of premium olive oils and balsamic vinegars Traditional Tuscan dinner with appetizers, homemade lasagna, and a typical meat course Dessert with Vin Santo for a complete dining experience A rich and immersive journey, perfect for those who want to experience Tuscany through its flavors, in a setting of quiet elegance.

For a taste of Tuscany, book this private vineyard tour that takes you behind the scenes to learn about wine production. You’ll have a private guided tour, where you can ask questions, sample wines, and learn about the vineyard and farm’s history. Then you’ll sit down to a private tasting, paired with local cheese, cold cuts, and bruschetta.

Run from a young team, Tenuta di Mensanello is a still authentic farm with the production of wines, beers and extra virgin olive oil. The activity shows how we work, our methods, our reality. At the end is possible to taste 3 wines and 3 oils guided by a sommelier.

On this wine-tasting tour, you will sample some of the region’s best Tuscan wines. Every glass is perfectly paired with local cured meats, cheeses, and a homemade pasta dish, or a full course meal, depending which wine tasting experience you choose (please inform us if you have any dietary restrictions).

Learn how to prepare classic Italian dishes in this private Chianti cooking class. Enjoy an intensive cooking session with an English-speaking chef, where you’ll learn how to prepare a pasta dish, sauce, and dessert. Enjoy the fruits of your labor and then participate in a wine tasting of Prosecco and Chianti. End the tour with a visit to 2,500-year-old underground Etruscan granaries.