Top San Gimignano Private and Luxury

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.

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 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.

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.

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 true soul of Tuscany with a unique food and wine experience immersed in the vineyards. Start with a welcome glass and enjoy a lunch prepared with local and seasonal products, artisanal cold cuts and Pecorino di San Gimignano. Savor a first course with black truffle (or classic alternative), followed by the dessert of the day. The experience includes a guided tasting of three selected wines and a tour of the vineyards and winery, to get up close and personal with the wine production and meet those who create it. Book now and experience the most authentic Tuscany, among flavors, views and tradition.

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.

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.

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.

Our San Gimignano Food Tour is a walking tour in small groups around the old town. The tourist is guided by a Local Expert able to explain every detail of the selected restaurants, their preparations, and the relevant history/curiosities. Our tours are a mix of high-quality gastronomy as a way of showing San Gimignano culture and lifestyle and a walking experience together with a local friend. Have a full meal in at least 4 stops: you will get the chance to try some of the most iconic San Gimignano dishes, such as wild boar cured meats, local pici with tomato sauce and pecorino, schiacciata with cured meats, and of course, Vernaccia wine!

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.

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!

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.

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.

Discover the beauty of Tuscany on an unforgettable e-bike adventure through rolling hills, vineyards, olive groves, and postcard-perfect countryside roads. Choose between a guided e-bike tour led by a local expert or enjoy the flexibility of an independent e-bike rental, perfect for exploring at your own pace. Ride along an easy and scenic route connecting San Gimignano with charming Tuscan villages and hidden corners of the countryside rarely reached by traditional tours. Whether guided or self-guided, you’ll experience authentic Tuscany in a fun, relaxing, and eco-friendly way. During the experience, stop at a traditional Tuscan winery and enjoy a delicious local lunch featuring bruschetta, handmade pasta, local cheeses, and a tasting of three red wines. Take in breathtaking vineyard views while savoring regional flavors and the warm atmosphere of rural Tuscany.

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.

Tuscany's countryside and rural vineyards are what draw many travelers to the region, and this small-group day trip pairs the two. Set out from either Florence or San Gimignano, before venture through olive groves and vineyards on horseback, and taking in views of the surrounding hills along the way. Then sit down to a traditional Tuscan lunch at a local estate, served with a tasting of its wines.

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.

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.

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.

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.

In the heart of Tuscany and Chianti. Hills, vineyards, unspoiled nature. Intact medieval cities. Unforgettable atmospheres.

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.