Top San Gimignano Walking Tours

Treat yourself to an epic 1.5-hour adventure in San Gimignano. With your very own personal guide, venture through the legendary hills of this majestic medieval town, renowned for its impeccable Romanesque and Gothic architecture. Bask in the glory of secular buildings and charming churches, stopping to sample local saffron and white wine. This UNESCO World Heritage site promises a nostalgic step back in time, not to mention views of the astounding medieval towers that adorn the skyline.

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.

Beautiful tour that will take you to discover the medieval town of San Gimignano. Not only its towers, but 1000 stories of pilgrims, merchants, travelers who made this place a very rich medieval destination. Churches, squares, alleys, and fantastic views. Join us to find out what tourists on their own often lose the beauty of Sa Gimignano

Take a deep dive into Tuscany’s traditional cuisine with this farmhouse cooking class. Connect with a local host and learn how to prepare a number of classic Tuscan dishes in her family kitchen, based on recipes passed down through the generations. Roll up your sleeves and make a selection of starters, first and second courses, and dessert, then sit down to a celebratory meal featuring the fruit of your labors.

Discover the secrets of truffle hunting among the enchanting hills of San Gimignano, one of the most fascinating gems of Tuscany. This exclusive experience will allow you to immerse yourself in the typical Tuscan landscape, accompanied by me, an expert truffle hunter for 3 generations, and my faithful dogs. During the excursion, you will learn the ancient truffle hunting techniques passed down by my family, and you will learn more about this rare and precious ingredient, typical of Tuscan cuisine. You will walk with me and my dogs in the woods, and this is the most fascinating part of the route, where you can see my dogs in action! While we will only perceive the scent of the woods, my dogs will be able to sniff the hidden aroma of truffles, and give us this precious ingredient that you will be able to savor in the most authentic way. At the end of the Tour you will receive very fresh truffles, including those just found, and instructions on how to preserve and cook them.

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.

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.

Visit two renowned wineries—and enjoy two separate tastings—during this full-day, small-group wine lovers’ tour of Tuscany’s Chianti region. Head to scenic, medieval-era Castellina In Chianti to enjoy Chiani wines paired with traditional cured meats. Then, head to Fattoria Lornano for a chance to sample even more local vintages along with extra virgin olive oil.

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.

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.

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.

Experience the beauty of Tuscany aboard a vintage Fiat 500 as you explore the scenic Chianti countryside. Travel through rolling hills, vineyards, olive groves, and charming medieval villages in a convoy of classic Fiat 500s driven by professional drivers. Along the way, stop at panoramic viewpoints and visit local wineries for guided tastings of Chianti wines, extra virgin olive oil, and balsamic vinegar. Enjoy a traditional Tuscan lunch at a winery, featuring local specialties and regional wines. Throughout the day, your tour leader will share stories and insights into Tuscan culture, making this a unique, authentic, and unforgettable Tuscan experience.

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.

Discover the authentic beauty of Tuscany on an unforgettable Vespa 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.

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.

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.

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.

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.

Let's go hiking through the vineyards of our estate! You will discover fields, vines, about the oil and wine production.

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.

San Gimignano, referred to as the 'Town of Fine Towers,' is a UNESCO World Heritage Site, and this walking tour takes you through its medieval heart. Start at Bagnaia Street, where you’ll enjoy views of the ancient defensive walls. Continue along Saint Matthew Street, lined with 13th-century buildings, and explore Rocca Park, offering panoramic views of the town. Admire the art inside the Cathedral of Saint Mary of the Assumption, then pass by the historic Town Hall. Wander through Cistern Square, rich in medieval monuments, stroll down the atmospheric Saint John Street, and finish with stunning views over the surrounding countryside from the Panoramic Point near the Monument to the Fallen.

Discover the most beautiful places of San Gimignano and the surrounding Chianti area starting from Florence with our professional photographer and our guide who will take you wonderful photos in the village and on the hills among the vineyards. You will not be a passive spectator, but you will be the center of attention, free to enjoy the experience without hindrances such as cameras and various devices. Once the tour is over the photographic material will be shared telematically already edited.

On this wine-tasting tour, you will sample some of the region’s best prosecco, rosé, and a variety of Tuscan red wines. Every glass is perfectly paired with local cured meats, cheeses, and various homemade pasta dishes (please inform us if you have any dietary restrictions). As you make your way through the villa’s multiple tasting rooms, you will discover that the Corbucci Wine Boutique not only produces excellent wine, they also make several other exceptional products, including limoncello, grappa, olive oil, and balsamic vinegar. All products are made from the finest, local ingredients and crafted with expert care. All good things must come to an end, and so must this tour. But there is no better way to conclude a wine-tasting experience than with a little more wine. To finish what promises to be an already wonderful experience, your gracious hosts will invite you to join them in raising a glass of Vin Santo—a traditional Tuscan dessert wine—to send you off with a sweet goodbye.