Top Siena Desserts & Sweets in 2026

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.

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.

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.

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.

This experience stands out by combining an indulgent cooking class on a panoramic terrace kitchen with a tour of vineyards and a 13th-century castle that's been in the family for 17 generations. Learn to make classic Tuscan dishes such as tagliatelle with Tuscan sauces and braised beef, and pair each with local wines for lunch. Then, tour the castle and wine cellar.

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.

Siena lovers, you will get the chance to breathe the atmosphere of the life of the Contrada and the Palio of Siena! An exclusive opportunity! An exciting experience lived with its protagonists: the Sienese people: vising the Museum and the Church of the Contrada Our guide will also lead you through the Piazza del Campo, where the most famous Palio in the world takes place every year on July 2nd and August 14th. We will also visit the Duomo of Siena, a gem set in a jewel city! We will continue to move into the world of the purest tradition with a tasting of typical Sienese sweets: Panforte, Ricciarelli and Cavallucci accompanied by Vin Santo del Chianti. These products, famous all over the world, maintain a high quality offered to the public in the past hundred years! The family of singer Gianna Nannini has been producing these sweets for generations and iat Caffè Nannini twe will stop and taste these specialities.

Many of Italy’s most charming hill towns are a challenge to reach with public transport. This private day trip offers seamless round-trip transport, giving you time to explore Volterra and San Gimignano at your own pace. Enjoy free time in both towns, with lunch at a Chianti cellar accompanied by a tasting of five different wines.

Take a break from the crowds in Siena, and spend an afternoon in the wine town of Montalcino on this group tour. Don't worry about hiring a car to get there, with transportation all sorted. Learn about Brunello di Montalcino wine and its production, along with wine tastings paired with local snacks. Admire views of the Tuscan countryside from this hill town as you discover the region’s generations-old winemaking traditions.