Top San Gimignano Holidays - page 2

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.

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.

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.

This experience uniquely combines the ancient art of falconry with Tuscany’s rich culinary traditions, all in the stunning setting of Podere La Marronaia. What makes this experience special? - Interactive falconry session: Watch hawks, falcons, and owls in flight and even hold a bird of prey. - Expert-guided insights: Learn about the history and techniques of falconry from skilled falconers. - Authentic Tuscan Merenda Break: Enjoy a tasting of organic wines, extra virgin olive oils, and balsamic vinegars paired with bruschetta, cheeses, and cured meats. - Breathtaking countryside setting: Admire panoramic views of the Tuscan hills and San Gimignano’s medieval towers. A perfect blend of nature, history, and gastronomy, offering an unforgettable Tuscan experience.

Take a break from sightseeing and connect with a local farming family just outside San Gimignano to tour their vineyards and olive groves. Learn how organic wine and extra-virgin olive oil are produced from your host and enjoy a relaxed tasting of both of these iconic Tuscan delicacies in the farmhouse garden overlooking the rolling hills and towers of San Gimignano.

Immerse yourself in the heart of Tuscany with a wine experience set in the scenic hills near San Gimignano. Begin with a warm welcome and an introduction to the estate, followed by a guided tour through the historic wine cellar, where traditional methods and passion come together. Enjoy a curated tasting of local wines, each paired with typical Tuscan products like cheeses, salumi, and fresh bread. The experience continues with a relaxing lunch on a panoramic terrace overlooking the vineyards. This journey offers not only authentic flavors, but also a deep connection to the land, its rhythms, and its winemaking heritage—a perfect escape for wine lovers and curious travelers alike.

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.

Learn how to prepare classic Italian dishes in this private Chianti cooking class. Enjoy an intensive cooking session with an English-speaking chef, where you’ll learn how to prepare a pasta dish, sauce, and dessert. Enjoy the fruits of your labor and then participate in a wine tasting of Prosecco and Chianti. End the tour with a visit to 2,500-year-old underground Etruscan granaries.

✅ Saffron-Themed Tuscan Lunch – Enjoy a four-course meal featuring San Gimignano’s prized saffron. ✅ Exclusive Wine Pairing – Each dish is complemented by a selection of organic wines that tell the story of our family. ✅ Olive Oil & Balsamic Vinegar Tasting – Discover the richness of our estate-produced extra-virgin olive oils and aged balsamic vinegars. ✅ Biodynamic Farming Insights – Learn about our sustainable production methods and the history of our farm. ✅ Authentic & Family-Led – Be welcomed by our family for a truly personal and immersive experience. ✅ Breathtaking Countryside Setting – Dine on a rustic farm overlooking vineyards, olive groves, and the Tuscan hills.

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

Cook Tuscan classics in this immersive 4-course class set in the rolling hills of San Gimignano at a charming local estate. Hosted through Cozymeal, this hands-on experience combines heartfelt storytelling with regional recipes passed down through generations. Menu - First course: Pappa al pomodoro — tomato and bread soup flavored with garlic and basil - Second course: Chicken cacciatora — a rustic red wine stew with vegetables - Third course: Grandma’s lasagna — baked layers of ragù, pasta sheets and creamy béchamel - Dessert: Tiramisu — layered with mascarpone, espresso and cocoa Paired with tastings of estate wines, olive oils and balsamic vinegar, this experience offers the perfect blend of flavor, history and Tuscan charm.

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.

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.

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.

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.

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.

This experience uniquely combines the ancient art of falconry with Tuscany’s rich culinary traditions, all in the stunning setting of Podere La Marronaia. What makes this experience special? - Interactive falconry session: Watch hawks, falcons, and owls in flight and even hold a bird of prey. - Expert-guided insights: Learn about the history and techniques of falconry from skilled falconers. - Authentic Tuscan Merenda Break: Enjoy a tasting of organic wines, extra virgin olive oils, and balsamic vinegars paired with bruschetta, cheeses, and cured meats. - Breathtaking countryside setting: Admire panoramic views of the Tuscan hills and San Gimignano’s medieval towers. A perfect blend of nature, history, and gastronomy, offering an unforgettable Tuscan experience.

Guided small group tasting in the countryside of San Gimignano, designed for those who want to understand Tuscan wine in a simple and authentic way. The experience is conducted by a local sommelier and combines tasting of wines representative of the territory with an accessible story about vines, landscape and traditions. Ideal for those visiting San Gimignano and looking for a relaxed, convivial and cultural moment, away from standardized tastings and crowded settings.

Podere La Quercia offers an intimate and personal experience hosted directly by the producer. With limited capacity and reserved tables for each booking, guests enjoy a relaxed atmosphere and genuine connection to the wines and the land. This is not a technical wine lesson, but a sensory journey through local flavors, stories and traditions. Ideal for travelers seeking authenticity, tranquility and a truly Tuscan countryside setting.

Indulge in a luxurious 90-minute epicurean adventure with this wine and evo oil tasting coupled with an exquisite truffle meal. Try various delectable dishes, perfectly complemented by a selection of fine wines. Begin your culinary journey with truffle appetizers and end it on a high note with the signature smoked beef and rucola salad. Top it all off with a decadent dessert of the day.

For a taste of Tuscany, book this private vineyard tour that takes you behind the scenes to learn about wine production. You’ll have a private guided tour, where you can ask questions, sample wines, and learn about the vineyard and farm’s history. Then you’ll sit down to a private tasting, paired with local cheese, cold cuts, and bruschetta.

Enjoy an authentic local experience that many travelers to Italy miss. Visit a small family vineyard to learn about the property and its grape varietals, and to visit the wine cellar. You'll learn more about Italian wines as you enjoy appetizers prepared with local products and taste three different wines produced at the estate.

If you're looking for a true Tuscan escape, this experience offers the perfect blend of authenticity, exclusivity, and breathtaking views. Set in our historic Vernaccia vineyard, it provides a deep connection to the land, traditions, and flavors of Tuscany. You’ll start with an insightful introduction to our biodynamic winemaking and olive oil production, learning the passion behind every bottle. Then, enjoy a private wine and extra virgin olive oil tasting, paired with a delicious Tuscan lunch or dinner, all while admiring the stunning views of San Gimignano’s famous towers. What makes this experience special? - A private setting in one of San Gimignano’s oldest Vernaccia vineyards - A guided tasting of organic wines and extra virgin olive oils - A farm-to-table Tuscan meal prepared with fresh, seasonal ingredients - A cozy yet elegant atmosphere, perfect for relaxation - An unforgettable journey into the heart of Tuscan flavors and traditions.