Top San Gimignano Tours by Duration

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Discover the magnificent architecture of the Renaissance on this full-day tour from Florence to Pisa and Lucca. Explore the famous marble monuments of Pisa’s Piazza dei Miracoli with a guide, including the city’s grand cathedral and vaulted cemetery. For the ultimate Pisa experience, climb the famous leaning tower and soak up panoramic views. After a stop at a local vintner’s shop for wine tasting, continue on to the medieval walled city of Lucca, where you’ll enjoy free time to stroll the well-preserved streets and squares your own.

Make the most of your time while your ship is docked, and avoid the hassle of planning logistics, on this private tour of Siena and San Gimignano. Drive through the Tuscan countryside to bustling Siena, walk its winding streets with your guide, and visit the Duomo and the 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.

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 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.

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.

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.

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.

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.

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.

Discover the authentic beauty of Tuscany on an unforgettable scooter 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.

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!

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.