Top San Gimignano Day Trips

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.

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 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!

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.

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.

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, tastings of four estate-made wines, and extra virgin olive oil.

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 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.

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.

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.

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.

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.

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 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.

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.

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

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.

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.

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.