Top Siena Dining Experiences

Sample Italy's flagship Brunello di Montalcino wine in the hills where it’s produced with this exclusive winery tour and tasting at a medieval castle. Join a sommelier for a stroll through the vineyards to learn about the history and production of Brunello at this family-run estate, then relax over a tasting that pairs three different wines with local specialties. Cap off your experience with a three-course Tuscan lunch.

Learn to cook traditional Italian dishes during this Tuscan cooking class in Siena. From homemade pastas to juicy cuts of meat, a professional chef leads you through a combination of family-favorite recipes and time-tested dishes, culminating with a shared meal and excellent wine. This class is held in a professional kitchen and limited to a small group of 15 people or fewer for a more intimate experience.

Discover the best of Siena’s traditional cuisine and food scene with the insights of a local insider guide on this small-group food tour. Set off with your foodie guide and group of just 12 fellow gourmands to visit the top artisan food shops, market stands, and other landmark eateries to sample a range of savory and sweet delicacies. Feast on charcuterie boards, pici pasta, ricciarelli cookies, and more as you explore the old town.

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.

There are places you visit, and others you truly experience. Here, among the hills of Chianti and the Crete Senesi, the experience unfolds slowly on our terrace overlooking the landscape, under the shade of an ancient white mulberry tree. This is not just a tasting: it is a moment to share, guided by those who produce the wine every day, in an atmosphere that is genuine and never staged. The wines tell the story of the land, the food accompanies them, and everything around you comes together to create something that stays with you. If you are looking for a real experience, made of details, hospitality, and time dedicated to you, this is the right place.

Sip Tuscan wine in a medieval castle during a tasting session in Montalcino. Hosted by a professional sommelier, the experience ensures you get the lowdown on the wine as you taste it. Enjoy three varietals including a glass of the prestigious Brunello di Montalcino DOCG, along with local bread or breadsticks and olive oil.

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.

Avoid the hassle of organizing transport and winery visits in Tuscany on your own. This small-group experience simplifies a day in Chianti, combining scenic travel with curated tastings at local wineries and time to explore Monteriggioni’s medieval charm. Enjoy a relaxed, well-paced outing that lets you focus on the region’s flavors and landscapes rather than the logistics.

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!

Discover the rich heritage of Chianti at Poggio San Polo’s Castello di Orgiale winery. Nestled among the picturesque vineyards, this historic castle sets the scene for a full winery experience in a small-group setting. Begin your visit with a warm welcome and a guided tour of the organic winery, where the art of winemaking comes to life. Explore the production areas and charming cellar filled with aging barrels, learning about the estate’s sustainable practices along the way. Savour an exclusive wine tasting, paired with local Tuscan delicacies and your olive oil, all explained by your host. Conclude your visit at the estate’s wine shop, where you can take home your favourite wines and local products from this enchanting winery. Highlights: - Guided tour of the organic winery and production areas - Exclusive wine tasting paired with local Tuscan specialties - Opportunity to taste estate-produced olive oil - Browse the wine shop for wines and local products - Small-group setting

Siena sits in the heart of Tuscany, known across the globe for its excellent regional cuisine. Delve into its traditional specialties with this foodie experience that combines a lesson covering Tuscan wines and gourmet delicacies plus a foodie stroll through the old town to sample them for yourself. Taste a variety of wines paired with cheeses and charcuterie, extra-virgin olive oil, bread, jams, and honey.

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.

There's no better way of immersing yourself in local culture than a cooking class. Get an authentic taste of northern Italy with this small-group cooking class in Siena. Led by a local chef, learn how to craft a delicious spread of Tuscan favorites plus a classic tiramisu. Afterward, enjoy the fruits of your labor as you savor your creations with your group and a glass of vino.

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

Take a break from sightseeing and head to the Tuscan countryside surrounding Siena to join a local forager on a truffle hunt through the woods. Follow your host and his pups across the hills as they search out precious tubers and learn all there is to know about truffles and the dogs trained to hunt them. Afterwards, head back to Siena to sample a number of truffle products in a local gourmet shop.

The Montalcino hills are home to some of Tuscany's most prestigious wineries, but sussing out these small producers on your own can be a challenge. On this tour, access a premier family-owned cellar set in a medieval castle for an exclusive guided tour and tasting with a group capped at just 15 people. Learn about the history and production of award-winning Brunello di Montalcino wines, then sample three different vintages paired with artisan Tuscan cheeses.

Tuscany is known for its excellent vintages, but the world of Tuscan wine can be overwhelming for a novice. With this informal wine class, you’ll get your bearings and learn to recognize the most important and storied wines of Tuscany. Delve into the history of Tuscany’s wine production, discover the different wine-producing areas and grapes, and sample a number of reds and whites from the region.

Enjoy a wine experience in the heart of Val D'Orcia, surrounded by the most authentic Tuscan countryside. Together with Tatiana, the owner of Poggio del Moro, or our oenologists, you will explore the Poggio del Moro estate - from the vineyards, to the oil mill, to the cellar and the barrique cellar - and you will learn the production process of our natural wines, free from pesticides and unnecessary production interventions. Poggio del Moro is an out of the ordinary boutique winery, an extraordinary open-air art gallery. In addition to our excellent wines, here you will find contemporary art exhibitions or artistic performances, which you can observe while visiting the cellar or tasting your wine in relaxation, an absolutely original and refined experience in an intimate and exclusive setting!

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.

Savor the fresh flavors of Sienese cuisine in this small-group morning or afternoon cookery class in Siena. Visit the home of Cesarina, your host, and roll up your sleeves for an immersive cooking experience—Sienese style. With all utensils and ingredients included, follow three traditional local recipes with helpful hints and tips from your host. Then, enjoy your food with a glass of wine among your fellow chefs.

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.

What makes this experience truly unique is the perfect combination of exceptional Brunello wines, authentic Tuscan cuisine and the intimate atmosphere of Paradiso di Cacuci, a family winery surrounded by the rolling hills of Montalcino. Guests are guided by expert sommeliers through the vineyards and ageing cellar, discovering the traditions, craftsmanship and passion behind Brunello di Montalcino production. The experience continues with a carefully curated tasting of premium Tuscan wines paired with a traditional Tuscan lunch featuring local specialities and fresh handmade pasta, creating a journey that combines wine, food and landscape in a truly authentic way. Far from crowded commercial tours, this immersive experience offers a refined and memorable taste of Tuscany in a relaxed and elegant setting. Each tasting is led by expert sommeliers, transforming every glass into a deeper journey through the world of Brunello di Montalcino.

Discover the tricks to making authentic homemade Italian pasta and tiramisu during a private cooking class in Siena. Set in a local home, your party will enjoy the undivided attention of your friendly and experienced host. After preparing two traditional types of noodles and the famous espresso-infused dessert - using some Italian family secrets - enjoy all three with a selection of local wines.