This square is the symbolic heart of Siena, deeply loved by locals who gather here to enjoy its lively yet timeless atmosphere. Framed by historic buildings, it sets the scene for our culinary journey. In a welcoming local setting, we’ll gather around a traditional Sienese chopping board, the true centerpiece of local conviviality, and enjoy a generous selection of locally produced cured meats and pecorino cheeses made from sheep’s milk of the surrounding countryside, ranging from delicately seasoned salumi to aged cheeses with deeper, more complex aromas, each shaped by land, climate, and time. As Italy is the homeland of wine, the hills surrounding Siena offer some of its most authentic expressions, and during the tasting you’ll sample carefully selected local wines that showcase different grape varieties, soils, and winemaking traditions, with each glass revealing the role wine plays in everyday Tuscan life and perfectly complementing the flavors on the board.

We continue our walk into the area surrounding the Pinacoteca Nazionale, where Siena’s artistic and culinary traditions intertwine. Here, we step into the city’s rich pastry heritage with a tasting of its most famous sweets. Soft almond ricciarelli, crunchy cantucci traditionally enjoyed with dessert wine, and the dense, spiced panforte all date back to medieval and Renaissance times. These desserts tell the story of Siena’s historic trade routes, noble kitchens, and festive family tables, offering a true taste of the city’s sweet tradition.

As we continue our walk through the historic center, passing through the area around the Duomo, we pause to enjoy a classic Italian espresso—short, intense, and aromatic. More than just a drink, caffè is a daily ritual in Siena, a moment to slow down, exchange a few words, and naturally conclude a meal, just as locals do at the bar or after a long lunch.

We continue along Via di Città, one of Siena’s most elegant historic streets, where we pause to taste a Bacio Senese, a small yet indulgent local chocolate specialty. With its soft texture and rich cocoa notes, this sweet reflects Siena’s refined pastry craftsmanship, offering a modern yet deeply local interpretation of traditional flavors.

We conclude our experience along Via dei Pellegrini with a taste of authentic Italian gelato, crafted using simple ingredients and a careful balance of flavors. Creamy yet light, rich yet refreshing, gelato is the perfect final pleasure, best enjoyed slowly while wandering through Siena’s historic streets, just as locals do on any day of the year.