Private tour of Siena and San Gimignano with dinner

Piazza del Campo is the heart of Siena and one of the finest examples of medieval urban planning in the world. Its unique shell shape - created by nine segments of brick pavement radiating downward toward the Palazzo Pubblico - was not accidental: it reflects the city's division into nine districts under medieval governance. Twice a year, during the famous Palio, it is transformed into a horse racing track lined with tens of thousands of spectators. Even on an ordinary day, its sweeping curves, surrounding medieval palaces, and the soaring Torre del Mangia make it one of the most beautiful public spaces in Europe.

Siena is divided into 17 districts called contrade - each with its own territory, flag, colors, patron saint, church, museum, and deep cultural identity. The contrade are not historical relics: they are living communities with active members, annual celebrations, baptisms, and funerals held under the district's colors. The rivalry between them - played out most dramatically in the Palio horse race - is intense and entirely genuine. Understanding the contrade system is the key to understanding Sienese identity, and your private guide will bring this fascinating world to life during the walking tour.

The dinner takes place at a carefully selected boutique winery nestled in the heart of the Chianti countryside — a family-run estate where wine has been produced for generations. Unlike large commercial wineries, a boutique winery offers an intimate atmosphere: smaller production lots, hand-harvested grapes, and a deep personal connection to the land. You will dine in a setting that combines rustic Tuscan elegance with genuine hospitality. The wine served at dinner comes directly from the estate, allowing you to taste the true expression of the terroir while your hosts share the story behind every bottle. It is not just a dinner — it is an authentic encounter with Chianti winemaking culture at its most personal.

There are few moments in Tuscany as breathtaking as watching the sun set over the Chianti hills. As the light turns golden and the shadows stretch across the vineyards, the landscape transforms into something that looks like a Renaissance painting come to life. Experiencing this from a boutique winery — glass of local wine in hand, the scent of the earth still warm from the day — adds a layer of emotion that no museum or city tour can replicate. The Chianti sunset is not just a visual spectacle; it is the moment when the pace of the day slows down and you feel completely immersed in the soul of Tuscany. It is one of those travel memories that stays with you long after you return home.

This private tour is an excellent choice for celebrating a birthday, anniversary, or any occasion that deserves a day that feels genuinely exceptional. The combination of medieval city walking tours, the beauty of the Chianti countryside, a sunset at a boutique winery, and a traditional five-course Tuscan dinner with expert wine pairings creates a full-day experience with a natural celebratory arc. Since the tour is fully private, every element can be shaped around your group - from the pace of the walking tour to the atmosphere at the dinner table.

For groups of 1 to 8 people, a full cancellation fee applies if you cancel within 7 days of your tour date or in case of no-show. For groups of 9 or more, availability and cancellation terms are available on request.