Top San Gimignano Private and Luxury

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.

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.

Tuscany is home to some of Italy’s most renowned cuisine and this tour is adapted for those with special dietary requirements. Enjoy a guided tour of the Tenuta Torciano Vineyards in San Gimignano, then visit the winery restaurant for a delicious 4-course lunch, accompanied by a wine tasting. Choose from a vegan, vegetarian, or gluten-free menu, depending on your preferences.

Sip on wine in San Gimignano during a Tuscan wine and food tasting. Try varietals such as Brunello di Montalcino, Vernaccia, and Chianti Classico, and learn about the distinct Tuscan winemaking regions as you drink. The tasting session is complemented by your choice of food. Select a winemaker option to include some light snacks, or upgrade to include a light lunch or dinner.

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.

We serves as a convenient mobile companion for exploring the ancient town of San Gimignano. This tour is specifically designed to help you discover the town in a short span of time (1 hour). Simply follow the route on the app's map, which takes you from the town gate of San Giovanni to the ruins of the Rocca fortress. You're guaranteed to see: The town walls of San Gimignano Renowned medieval skyscrapers Palazzo Comunale Duomo of San Gimignano and other The itinerary comprises 14 points, each accompanied by illustrations and audio commentary penned by a professional historian in an accessible, non-academic style. The audio guide is best enjoyed through your headphones, allowing you to immerse yourself in fascinating stories and legends at your own pace, without the need to keep up with a tour group. Once the tour is downloaded, the app functions offline. If you only have a few hours to visit San Gimignano, make the most of it with the audio guide.

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.

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.

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.

Discover the sights and flavors of Tuscany by e-bike on a private Chianti cycling tour. Meet your cycling guide directly at the starting point or choose pickup at your San Gimignano hotel. Then set off along quiet roads and trails, the perfect way to immerse yourself in the region’s world-famous landscape. Pedal your way to a traditional family farm and wine cellar. There you enjoy a filling meal featuring local specialties and paired with the estate's own wines.

Once the tour is booked, you can come to our rental point to collect the bikes, so you can start with our virtual guide, which will accompany you step by step. The tour is a scenic loop starting from San Gimignano, along urban roads, white gravel roads, vineyards, olive groves, and with continuous views of its famous medieval towers. The route is 26 km with 500 m of elevation gain: it is smooth and non-technical, ideal by e-bike and suitable for everyone, as long as you have a minimum level of confidence on dirt roads and on a few short climbs. Along the itinerary there is a stop at Fattoria Poggio Alloro, with beautiful views over San Gimignano, perfect for a snack break or to end the tour with a wine tasting and cellar visit. A medieval village on the Via Francigena, San Gimignano is now a UNESCO site: of the more than 70 towers from the 14th century, 14 still remain today.

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.

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.

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.

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.

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.

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.

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.

Enjoy a celebratory evening in Tuscany with a romantic dinner and wine tasting. After a relaxing walk around the historic San Gimignano property, settle into a delicious multi-course meal. Sample an appetizer of Tuscan cheeses, salami, and bruschetta before moving on to truffle lasagna, roasted meat, and vegetables, and a dessert of vanilla ice cream with Balsamic vinegar. Take a winery tour and taste current and vintage reserve wines.

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 Gimignano, where you’ll taste local honey, cheeses, and fresh bruschetta with seasonal ingredients. Continue to a traditional winery for a light lunch with balsamic and olive oil tastings. Adults can enjoy a tasting of three Tuscan wines, while younger guests and non-drinkers are treated to grape juice or refreshing soft drinks. Finish the day with free time to explore the medieval streets of San Gimignano before returning to Florence. A delicious and family-friendly Tuscan experience that everyone will love!

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.

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.

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.