Top Siena Dining Experiences

Nibble your way through one of Italy’s most spectacular medieval cityscapes and learn about its traditional sweet and savory treats with this Siena street food tour. Meet a local foodie guide and discover the top spots in town for everything from charcuterie to pastries at food shops and market stalls. Enjoy the relaxed pace and personal attention of a small group and come away with a deeper understanding of Sienese cuisine.

Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.

What makes the experience unique is the authenticity and passion of a family-run farm, nestled in the Chianti Classico hills, just a few minutes from Siena. Guests can walk through the vineyards, discover the secrets of Sangiovese and learn about the philosophy that Guides each stage of cultivation. The guided tasting offers wines accompanied by extra virgin olive oil and typical local products, enhancing the flavors and characteristics of the territory. Each glass tells a story of tradition and care, for a genuine, convivial experience immersed in the beauty and scents of Tuscany.

This experience is led by Paolo Nenci, one of Italy’s first “digital farmers”, followed by thousands of people online for his innovative approach to wine and agriculture. The winery was awarded in Dubai in November 2024 for excellence in extra virgin olive oil, a recognition of quality and craftsmanship. You will also taste wines produced with traditional methods, including the historic Vin Santo made with a fermentation mother dating back to 1820. An authentic, award-winning experience in the Tuscan countryside near Montepulciano, far from mass tourism.

Enjoy an immersive experience in Italian culture and savor a traditional aperitivo on this private cooking workshop in Siena. Visit a local Italian home, and meet your host and instructor. Using fresh, local ingredients, prepare five tantalizing nibbles to accompany a refreshing glass of bubbly or Tuscan wine. Relax over a drink among new friends, and learn of role the aperitivo plays in Italian society.

There's no better way to discover Italy's culture from the inside. Our national network of expert Italian home winemakers offers the finest Italian wine and dine experiences. Located in the enchanting Chianti Hills, between Florence and Siena, our winery invites you to embark on a sensory journey through the heart of Tuscany. Embark on a captivating journey through the Chianti Hills, indulging in the exquisite flavors of wine, cheeses, honey, and local cold cuts! Immerse yourself in the art of winemaking with a vineyard tour and cellar visit, where you'll discover the secrets of Sangiovese and its meticulous vinification and aging processes. Enjoy a tasting of four exceptional wines, perfectly paired with samples of the farm's own cold cuts, goat cheese, and honey. And that's not all - get ready for an introduction to the fascinating world of beekeeping!

Immerse yourself in the culinary culture of Siena with a small-group cooking class at the home of a "Cesarina," an Italian cook and host. You'll visit a local market and food shops first, and then start the lesson to learn how to make three Sienese dishes. Finally, you'll be rewarded by enjoying your creations accompanied by a glass of wine.

Stroll the charming Medieval streets of a Tuscan hill town with this 2-hour private tour of Siena. Learn about Siena's hidden gems from a knowledgeable guide in between visits to its most popular sights.

The academy is much more than a cooking school where you can learn traditional dishes, it is an authentic experience that blends tradition, local flavors and Tuscan hospitality. We stand out for the careful selection of ingredients of the territory, many of which are zero km. Position is the very framework of experience. Immersed in the medieval streets a few steps from Piazza del Campo, it gives our guests a unique and suggestive atmosphere where every experience is accompanied by the beauty of Siena

Immerse yourself in the culinary traditions of Siena during a small-group cooking class set in a charming historical villa. Discover the secrets of Tuscan cuisine and learn to prepare authentic Italian dishes, including ravioli and tiramisu, under the guidance of a skilled chef. After, indulge in a wine tasting, savoring the flavors of local wineries. Finally, tour the villa and admire its rustic charm and surroundings.

The best way to learn about and appreciate Tuscany’s beloved cuisine is in the home of a local. With this experience, take a deep dive into authentic dishes from Siena with a private hands-on lesson with a home cook, or “Cesarina”. Learn to prepare three traditional Sienese pasta recipes and enjoy your creations paired with local wines to end your class.

A wine expert who will guide you through the tasting journey. Wine tasting that includes 2 Spumante and 3 Red Wines. Olive Oil tasting that includes Truffle, Chili Pepper, and Extra Virgin Olive oil. Aceto Balsamico tasting that includes Onion and Modena vinegars. Tuscan appetizers: Salame toscano, finocchiona, prosciutto crudo toscano, pecorino, bruschetta with fresh tomato and basil, cialda di pane tostato with Extra Virgin Olive Oil. First course: Penne al ragù or Penne al pomodoro. Second course: Arista with roasted potatoes. Dessert: Cantuccini and Vinsanto

Feel like a local, as you accompany your own private cesarina (chef) through a traditional, bustling marketplace in Siena, picking up fresh ingredients as you go. Afterwards, enjoy an exclusive cooking demonstration in your chef’s own home—Italian hospitality at its finest—before tucking into the four-course meal they prepare.

Want to get your hands dirty with dough? This is the cooking class experience for you! You will learn how to cook simple and delicious recipes with our Italian Chef to add a taste of Tuscany to your table while tasting our exclusive wines. After the cooking class, our wine expert will teach you the basic information for a wine tasting and will explain how wine permeates the culture of this territory. This is more than just a simple cooking class; it’s an experience that engages all your senses, leaving you with a deeper appreciation for the art of winemaking and the Tuscan cuisine. Whether you’re a wine connoisseur or a novice, this cooking class promises a memorable and enriching experience.

⭐ Experience Highlights — What’s Included Historic Tour Explore our 1810 cellar, family chapel, and ancient olive press. Immerse yourself in Montechiaro’s heritage. Wine Tasting 3 organic wines: Chianti & Super Tuscans. Sommelier-led pairing with local specialties. Fresh & Organic Ingredients Garden-grown vegetables Extra virgin olive oil & organic jams Local cheeses (fresh & aged) Traditional Tuscan Flavors Bruschetta with tomato & basil, Artisanal cured meats Truffle sauces Notes Reservation required Dietary preferences/intolerances accommodated ✨ Taste Tuscany, sip tradition, and enjoy an unforgettable experience! ✨

The academy is much more than a cooking school where you can learn traditional dishes, it is an authentic experience that blends tradition, local flavors and Tuscan hospitality. We stand out for the careful selection of ingredients of the territory, many of which are zero km. Our location is the very framework of the experience. Nestled in the medieval streets a few steps DA piazza del campo, it gives our guests a unique and suggestive atmosphere where every experience is accompanied by the beauty of Siena.

A complete and exclusive tasting experience designed to immerse you in the daily life of our winery – between vineyards, cellar and the artisanal precision that shapes our wines. The Grand Experience features an extended selection of our most representative labels, combining minerality, elegance and origin in a refined tasting journey.

Immerse yourself in Italian culinary traditions with a hands-on pasta and tiramisu cooking class. Learn how to roll fresh pasta ('sfoglia') by hand and prepare two iconic pasta dishes from scratch. Plus, master the art of making Italy’s beloved dessert, tiramisu. Join a small group and share your love for Italian cuisine while connecting with fellow food enthusiasts. The experience begins with an Italian Aperitivo to kickstart your cooking adventure. Hosted by Cesarine, Italy's oldest network of home cooks, this class offers a unique opportunity to learn from passionate local hosts who share authentic regional specialties passed down through generations. A perfect way to experience the heart of Italian culture!

Our business stands out for offering a unique experience that combines equestrian adventure with the sophistication of wine tasting. We are committed to taking travelers on a sensory journey through breathtaking landscapes and fine wines, enriching their experiences with the magic of poetry that permeates this land. We are proud to offer an opportunity to connect with nature in meaningful and memorable ways, while immersing ourselves in the timeless beauty of this destination. We invite our guests to book with us for an experience that will leave them inspired and satisfied, enriched by the unique combination of adventure, culture and gastronomy that only our business can offer.

Visit a family business that has been producing wine for over 70 years! Tour of our vineyards, winery and guided tasting accompanied by a typical Tuscan cutting board. Ideal experience for those looking for a panoramic aperitif in the Chianti hills, immersing themselves in the relaxing Tuscan countryside and knowing the wine production process in small steps.

Tenuta Poggio al Rigoloccio is located in Gavorrano, in the heart of the Tuscan Maremma, a region renowned for its historic iron and pyrite mines. This extraordinary mineral-rich soil, combined with the constant sea breezes, gives our wines their elegance, freshness, distinctive minerality, and remarkable ageing potential. Our story is one of an exceptional terroir, but above all of the people who bring it to life every day. Working among the vineyards and in the winery, we are guided by passion, dedication, and deep respect for tradition, carefully following every stage of the grapes' ripening. At the same time, we continuously refine our vineyard practices to enhance the mineral character of the soils and express the authentic identity of every wine. Guided by the vision and expertise of Cellar Master Gerhard Sanin, we transform these grapes into wines of structure, character, and personality—authentic expressions of the land from which they originate.

Spend a day of nature and good taste! Truffle hunting in the vineyards and woods of Chianti, with expert truffle hunters and their dogs. Tour of a family business with visit to the vineyards and winery. Light lunch based on seasonal truffles with 3 courses to enhance the taste. Tasting of 3 wines, paired with each dish. An ideal experience for those who want to learn about the world of truffles, stay in contact with nature and enjoy a refined lunch accompanied by our best wines at the end of the experience.

Tuscany and Pisa have always been synonymous with rich and fine food and there are many and varied aspects of the city that you can discover with our food and wine tour. Along with the locals, who live the city every day, we will take you to the city’s most popular and historic places and we will make you try the real “pisano” taste and flavours: starting from the typical rural tuscan salamis and cheeses, to the traditional focaccia “cecina” (from italian “ceci”: chickpeas), to conclude with an ice cream in one of the historical ice-cream stores in the city. If you want to really enjoy Pisa food tradition walking downtown and entering in restaurants that only local people know, join our Pisa food tour!

Immerse yourself in the heart of Chianti Classico with a vineyard tour that will reveal the traditional techniques behind the exquisite wines. This unique experience includes a guided walk through the picturesque vineyards, where you will discover a passion for viticulture. End your visit in a charming tasting room, tasting three wines and an extra virgin olive oil from your own production that embody the essence of Tuscany. Everything will be accompanied by a small surprise that will leave you with an indelible memory.