Top San Gimignano Wine Tasting Tours

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.

A sunset dinner with panoramic views over San Gimignano. As golden light falls over the medieval towers, the terrace becomes an intimate setting where wine, cuisine, and landscape come together. What makes it special: Exclusive panoramic terrace at sunset overlooking San Gimignano Guided tasting of 8 wines, including Chianti Classico Riserva and Supertuscan Selection of premium olive oils and balsamic vinegars Full Tuscan dinner with appetizers, homemade lasagna, and a traditional meat course Dessert with Vin Santo to conclude the experience A refined and atmospheric evening, perfect for those who want to experience Tuscany at its most scenic and authentic moment.

Wine tasting in Tuscany might seem overwhelming when you don’t know where to start. But, this San Gimignano wine experience makes it easy, with a prebooked tasting session of up to five local wines, paired with local snacks. As well as a tasting, you’ll tour the vineyard and cellars, learning about the local vernaccia white wine grape and the Chianti Colli Senesi area that produces some of the region’s most esteemed wine.

San Gimignano is surrounded by quiet countryside dotted with small wine estates. Visit one of these traditional farms and connect with local hosts on this tour and wine tasting experience. Take in the organic farm's garden, orchard, vineyard, olive grove, "vinsantaia" aging room, and cellar. Then enjoy a tasting of eight organic wines of your choice paired with the farm's own olive oil plus local cheeses and cold cuts and other culinary combinations.

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.

100% Organic & Family-Run: You won't find a corporate atmosphere here. We are a real working farm, and we share the same passion for sustainability that we put into every bottle of our organic Chianti Classico. The "Zero-Meter" Connection: Our tasting terrace overlooks the exact vines your wine came from. You can trace the entire journey of the grape—from the soil beneath your feet to the glass in your hand. Small-Scale Intimacy: We prioritize quality over quantity. Our groups are kept small to ensure you have plenty of time to ask questions, savour, and truly soak in the silence and colors of the Chianti countryside.

A few steps from San Gimignano, there is a splendid family-run winery. Here you can taste the typical Tuscan products: starting from the wine up to tasty local croutons. You will visit the cellar, the vineyards, and all the places where the wine comes to life. You will listen to stories, and curiosities, and you will learn the winemaking processes that make Tuscany and Chianti areas to be protected and loved. You will discover the secrets of wine and grapes and the best combinations with strictly typical foods. Do not miss the opportunity to combine Tuscan wine with appetizing foods (such as cheese and ham) and find out how wines are produced in a real cellar. You can have a lovely tasting of 4 wines accompanied by snacks of typical products preceded by a tour of cellars and vines.

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.

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.

An elegant introduction to Poggio ai Laghi, just minutes from San Gimignano. Set among rolling Tuscan hills and vineyards, this experience offers a relaxed and authentic atmosphere where time slows down and every detail reflects local tradition. What makes it special: Panoramic countryside setting near the historic center Guided tasting of 5 wines, including Chianti Classico, Riserva, and Supertuscan Selection of premium olive oils and balsamic vinegars Traditional Tuscan food pairing with cured meats, bruschetta, and local specialties Dessert with Vin Santo, for a complete gastronomic journey A refined yet welcoming experience, perfect for those who want to discover the true flavors of Tuscany in a single, memorable tasting.

Let's go hiking through the vineyards of our estate! You will discover fields, vines, about the oil and wine production.

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.

During this two-hour experience, you will have the unique opportunity to walk among the olive trees surrounding the winery with your picnic basket and delicious dishes ready to satisfy your taste buds. You will be free to choose the ideal place to sit, spread your blanket and admire the surrounding landscape while enjoying your lunch.

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.

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.

Get ready for a truffle-tasting adventure with this 3-hour lunch and hunting experience in San Gimignano. Your certified guides will take you to the prime truffle grounds and teach you everything you need to know about these esteemed delicacies. With your four-legged friends leading the way, you can experience the thrill of hunting for truffles in the midst of nature. Return to Podere La Marronaia for a mouth-watering truffle lunch, perfectly paired with organic wines and olive oils.

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.

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.

Sip, swirl, and savour six delicious wines on a small-group tasting tour in San Gimignano. Learn how grapes become wine from a local expert as you enjoy paired bites and ask questions. Share tasting notes with your group and pick up insights you might otherwise miss. This one-hour tour is perfect for fitting into a busy day exploring the surrounding area of the beautiful region.

Tuscany is famous for its fine wines, UNESCO-listed landscapes, and historic cities, and this small-group day trip from San Gimignano ticks off all three. Enjoy wine tasting in the Chianti wine region; explore historic Montalcino; and sample the famous Brunello di Montalcino wine. Tour includes hotel pickup and drop-off.

Skip a regular restaurant meal in San Gimignano, and enjoy a meal in a local’s home instead. You’ll savor a 4-course menu, featuring home-cooked recipes that have been passed down through the family of your host—a Tuscan local who’s part of the Italian Cesarine network of home cooks. It’s a fun experience for a group of family or friends who want to experience some local culture while in town.

The tasting of the five wines and their combinations will be presented and served in our equipped and comfortable tasting room, where all our guests, even if spaced and safely, can enjoy a convivial and unique experience! For all those who have particular diets or intolerances, upon notice at the time of booking in the "notes" field, we are able to meet most dietary needs. The price of the tasting includes everything: tasting, water and food pairings. The structure of the Rocca di Montestaffoli does not provide bar service (coffee, tea, soft drinks, spirits, packaged foods, etc.) It is also possible to participate in the tasting with children, for them our staff will prepare a selection of gastronomic excellences at a cost of € 8 per child.Remember that by law it is forbidden to administer alcohol to minors.

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.