Best Dining Experiences in Siena 2025

Siena , Tuscany

From $ 71.70

Are you a curious and thirsty traveler looking to uncork some of Tuscany's wine secrets? Come to the Tuscan Wine School for an informative and fun class to learn about Tuscany's most important, traditional wines led by an English-speaking local expert. Discover the history and legends behind Tuscany's most significant wines and learn to swirl, smell and sip your way through the different types and styles of wine. The tasting of wines is enhanced by a series of different sample foods, and food pairing tips will be discussed, leaving you able to make better choices when choosing from local names in the city's restaurants.

Siena , Tuscany

From $ 65.73

Leave Siena behind and hike part of Via Francigena, an ancient pilgrimage route through rural Tuscany, followed by a wine tasting in the village of Monteriggioni. Embark on a 5-mile (8-km) trek that passes through the heart of the Tuscan countryside, past picturesque castles, villages, vineyards and ruins. Once you reach the medieval walled village of Monteriggioni, reward yourself during a wine tasting session, where you will sip on 3-4 different local, organic wines. Return to Siena at your own leisure by bus (bus tickets provided).

Siena , Tuscany

From $ 70.39

Enjoy an exclusive wine tasting combined with a typical Tuscan lunch in a medieval Castle in the heart of Montalcino.

Siena , Tuscany

From $ 33.46

The terrace, the white mulberry tree and the hills of Chianti Classico become part of your memory, a moment that will remain engraved in your soul. With each taste, your palate dances in tune with the authentic flavors, while your gaze gets lost in the breathtaking panorama that surrounds you.

Siena , Tuscany

From $ 38.84

Enjoy 1.5 hour wine tasting experience in an elegant medieval Castle in the heart of Montalcino. Together with an expert sommelier, don't miss the chance to discover and taste some of the best Tuscan wines in an exclusive location.

Siena , Tuscany

From $ 71.70

Savor Siena offers a chance to not only taste, but to learn about Tuscany’s wealth of foods, with a particular focus on what's Sienese. See how the local foods tie into local Tuscan culture and history, and enjoy many delicious bites of local savory and sweet products and wine with your local expert guide. The food and wine class is partly a tour around town to taste from local vendors and discover the hot spots for foodies so you will need to be physically fit to walk around a mile.

Siena , Tuscany

From $ 59.75

Embark on a sensory journey at Poggio ai Laghi, nestled in the heart of Tuscany, Italy. This unique tasting tour is not just about savoring the flavors of exquisite wines, oils, and vinegars, but it’s an immersive experience that engages all your senses. The tour begins with a tasting of Poggio ai Laghi wines dedicated to Donna Ava and her handmaids. Each sip tells a story of the rich Tuscan soil and the meticulous care taken in every step of the winemaking process. Next, you’ll sample the estate’s olive oils as well as the special chili pepper oil and white truffle olive oil. The tour concludes with a sampling of Poggio ai Laghi artisanal vinegars: the balsamic viegar which is an all-Italian excellence and the special vinegar with Valdelsa onions.. The wine expert will guide you through each tasting, explaining the production process, the flavor notes to look out for, and the ideal food pairings.

Siena , Tuscany

From $ 106.36

Paradiso di Cacuci is a winery located in a small “corner of Paradise“ in the northwestern area of ​​Montalcino. Our wine production is centered on the perpetuation of the tradition which, together with a more modern model and in compliance with the values ​​of the Brunello Consortium, uses only from our vineyards which are respectively divided into; 5 ha Brunello di Montalcino, 1 ha. Rosso di Montalcino and 5 ha. di I.g.t. Sangiovese. Welcomes, by reservation, individual visitors and small groups offering guided tastings that give the opportunity to get to know the production directly, starting from the wine making process to the discovery of the final result, giving a unique and unforgettable experience. Our tastings are only private and by appointment only to guarantee you our best services.

Siena , Tuscany

From $ 82.46

Paradiso di Cacuci is a winery located in a small “corner of Paradise“ in the northwestern area of ​​Montalcino. Our wine production is centered on the perpetuation of the tradition which, together with a more modern model and in compliance with the values ​​of the Brunello Consortium, uses only from our vineyards which are respectively divided into; 5 ha Brunello di Montalcino, 1 ha. Rosso di Montalcino and 5 ha. di I.g.t. Sangiovese. Welcomes, by reservation, individual visitors and small groups offering guided tastings that give the opportunity to get to know the production directly, starting from the winemaking process to the discovery of the final result, giving a unique and unforgettable experience. Our tastings are only private and by appointment only to guarantee you our best services.

Siena , Tuscany

From $ 106.36

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.

Siena , Tuscany

From $ 106.36

Dive into Siena like a local foodie. Explore your Cesarina's most trusted artisanal food shops, tasting as you go. Visit a selection of small local shops, learn about the typical products of the city while tasting them. A delicious way to discover Siena and its gastronomy! • Street food tasting tour • Explore your Cesarina's most trusted artisanal food shops • Sample some of Siena typical street food staples • Do some sightseeing in Siena as you walk from tasting to tasting • Small-group tour with a maximum of 12 people for an authentic food experience Le Cesarine is Italy’s oldest network of home cooks all over the country in more than 120 cities. They are passionate and welcoming hosts that open the doors of their own homes to curious travellers for immersive culinary experiences.

Siena , Tuscany

From $ 113.53

Off-road mini tour in a vintage Jeep through the landscapes of the vineyards. Taste Poggio ai Laghi premium wines, oils & vinegars. Enjoy the Tuscan Appetizers that enhance the flavors of each wine. Our wine expert will enhance this experience with Art & History.