Best Siena Dining Experiences in 2026

Siena , Tuscany

From $ 69.81

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 $ 84.94

Siena is one of Tuscany's best-loved cities, a fixed stop for those in the Chianti region. A destination for many visitors, Siena is internationally known not only for its picturesque, medieval historical centre, the famous Palio di Siena in Piazza del Campo and the colourful countryside that surrounds it, but also for the delicious cuisine it offers. It is impossible not to think of the excellent dishes and exquisite wines that can be found in the city. Thanks to our gastronomic tour of Siena, we will discover together the secret dishes and recipes of the Sienese tradition.

Siena , Tuscany

From $ 69.81

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 $ 68.53

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

Siena , Tuscany

From $ 32.58

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 $ 37.82

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 $ 69.81

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 $ 58.18

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 $ 81.45

Experience the hospitality of Poggio ai Laghi with your loved ones, in our authentic Chianti winery. This cozy lunch, leaves you with a deeper appreciation for the art of winemaking and the beauty of the Tuscan winemaking history. Our wine expert will walk you through the tasting journey. As you learn about the winemaking process and the passion behind each bottle, the food and wine experience becomes more than a meal—it becomes a memory, and quite possibly your most cherished souvenir from the Tuscan countryside. You’ll sample a selection of our finest wines, showing the skill and dedication of our winemakers. You’ll also savor the winery’s exquisite oils and vinegars, each one crafted with the same attention to detail and quality as the wines.

Siena , Tuscany

From $ 80.29

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 $ 65.16

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

Siena , Tuscany

From $ 81.45

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.

Siena , Tuscany

From $ 89.60

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.