Top San Gimignano Tours, Sightseeing & Cruises - page 2

Spend a couple of hours indulging your love of Tuscan wine and sharpening your tasting skills at Tenuta Torciano Vineyards. Begin with a quick walking tour of the estate while learning about the vineyard’s history, then enjoy a wine tasting and food pairing, a complimentary lunch, and lessons from an expert focused on wine etiquette and manners.

Navigate through the picturesque landscapes of Tuscany with the Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.

Step off your ship and into a waiting vehicle for a private tour of Siena and San Gimignano. Enjoy the drive through the Tuscan countryside to bustling Siena, walk its winding streets with your guide, visit the Duomo and central square, famous for the annual horse race. Next, head to the charming UNESCO-listed town of San Gimignano and immerse yourself in its medieval surroundings before returning to port in Livorno.

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. Savor a sumptuous Tuscan lunch featuring homemade pasta and local delicacies, paired perfectly with the 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.

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.

Tuscany is Italy’s gastronomic heartland and a cooking class is the perfect way to discover the region’s rich culinary traditions. On this 3-hour small-group cooking class, pick up tips and techniques from a local chef; create traditional recipes such as antipasti, bruschetta, and pasta dishes; then enjoy a homemade meal, accompanied by Tuscan wines.

During an e-bike tour in Certaldo, you will experience a perfect blend of medieval history, breathtaking landscapes, and authentic Tuscan culture. This area is ideal for cycling, thanks to its rolling hills, scenic country roads, and charming historic center. Certaldo Alto – The Medieval Heart One of the highlights of the tour is reaching Certaldo Alto, the beautifully preserved hilltop medieval village. Here you can explore: Narrow brick-paved streets, ancient walls, and historic gateways Palazzo Pretorio, the symbol of medieval civic power, decorated with coats of arms and frescoed rooms The House of Giovanni Boccaccio, birthplace and home of the famous author of The Decameron Historic churches such as Saints Jacopo and Filippo, where Boccaccio is buried From the village, you’ll enjoy stunning panoramic views over the Val d’Elsa countryside. Tuscan Countryside Riding Outside the town, the route continues through classic Tuscan scenery: Vineyards, olive groves,

Navigate through the picturesque landscapes of Tuscany with the Tootbus Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.

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.

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.

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.

Bus tours can make many stops in a short amount of time, but they can be plodding affairs and leave travelers feeling out of touch with the landscapes they drive through. This tour—which takes to the roads of the Chianti region on vintage Fiat 500s—allows visitors more fun and the chance to drive themselves while they follow a guide. Pass medieval villages, rolling countryside, and wineries, and stop for a Tuscan lunch and wine tasting.

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.

Explore the Tuscan countryside near San Gimignano on a classic Ape Calessino—a 3-wheeled Italian tuk-tuk. Depart from the Poggibonsi—near San Gimignano and Siena—and hit the panoramic roads of Tuscany and the Chianti hills, passing vineyards, cypress forests, and Tuscan rural houses. Then, stop at a local winery for an authentic Tuscan meal with wine and olive oil tastings.

This is a one of a kind treasure hunt. It takes place in a real medieval historic building, mostly decorated with coats of arms that belonged to the noble Florentine families. Ideal for a group of friends who want to spend a different day than usual, for corporate team building activities but also for a family with teenagers. The puzzles are fun and will stimulate your imagination. The palace in which the hunt takes place is simply magical.

The 15-minute flight offers stunning views over Tenuta Torciano and its vineyards, passing over San Gimignano, Certaldo, and the Chianti vineyards. Upon landing, you'll return to Tenuta Torciano. Here, our wine instructor will greet you with a glass of wine and introduce you to the company's history. You will tour the cellars, barrel room, vineyards, and gardens. Depending on the season, you'll enjoy a delicious lunch either in the vineyard or in a private room inside the cellar. The lunch experience includes a vertical tasting of traditional Tuscan gourmet products, featuring special vintages and limited editions. During this time, you'll learn how to properly pair food and wine. The helicopter tour, visit, and lunch will take around 3 hours. - Appetizer: typical Tuscan cold cuts and cheeses with local bruschette - First Course: truffle lasagna or Tuscan ribollita with vegetables - Second Course: roastes meat with vegetable side dish - Dessert: cantuccini biscuits with dessert wine

Hop on a scooter to explore the rolling landscapes of Chianti on this 7.5-hour Vespa tour from San Gimignano. Settle on a Vespa and ride around vine-coated hills, cypress groves and old villages, soaking in the views of this famous wine producing region. Your tour includes a wine tasting and lunch, plus the option to ride as a passenger with an escort driver or to upgrade to drive your Vespa.

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.

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 contact with nature and with truffle dogs makes it a unique experience of its kind. It is very fun and special.

Enjoy sky-high views over the Piedmont hills without the hassle of navigating unfamiliar roads at dawn on this hot air balloon flight, with an upgrade to include round-trip transfers from Milan. Enjoy the ease of hotel pickup and marvel at the vineyard-covered hills and Alpine peaks from the unique vantage point of a hot air balloon. On landing, toast your experience with a glass of sparkling wine or juice before heading back to Milan.

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

This exclusive truffle adventure sets itself apart by combining the thrill of truffle hunting with a hands-on Tuscan cooking class, offering a genuine farm-to-table experience in an intimate setting. Guided by a knowledgeable truffle guide, chef, and sommelier, you’ll explore the woods close to our farm ( 5/10 minutes driving from the meeting point), uncovering the secrets of truffle cultivation before heading into our rustic kitchen. Here, you'll master the art of fresh handmade pasta, craft delicious bruschetta, and prepare delicious truffle-infused dishes, all using authentic local ingredients. What makes this experience truly unique? The personalized attention, immersive cultural connection, expertly paired organic wines, and e.v.o. Olive oils and balsamic vinegar complement every dish. More than just a class, this is a luxurious, hands-on journey into the heart of Tuscan flavors—an unforgettable experience for truffle lovers and food enthusiasts alike! ✨

A place of centuries-old history, the San Gimignano countryside offers a view of a gentle expanse of hills, ideal for a journey to discover the food and wine traditions of Tuscany. The vines of Vernaccia, the famous white wine of San Gimignano, will accompany your journey. Traveling through these landscapes is a real pleasure for the eyes: on the small provincial and farm roads, the hills chase each other and always show suggestive views. The walk will start from our farm and then continue to Pieve di Cellole, where if you want you can enjoy a glass of Vernaccia at sunset, and then end again at Fattoria Sant'Andrea for a total of 9km covered.