Private Guided Tours in Siena: History, Art & Living Traditions

Siena is one of Tuscany’s most captivating cities — intense, proud, and deeply rooted in tradition. A private guided tour of Siena allows you to truly understand what makes the city so unique, beyond its beautiful architecture. With a knowledgeable local guide, you’ll explore Siena’s rich history, artistic heritage, and strong sense of identity at a pace that suits you.

From the very beginning, your guide will help you understand Siena’s long and complex relationship with Florence, a rivalry that shaped much of the city’s political, cultural, and artistic development and still echoes in local pride today.

Piazza del Campo, the Duomo & Siena’s Iconic Landmarks

No visit to Siena is complete without experiencing its two most famous landmarks. During your private walking tour, you’ll be introduced to:

• Piazza del Campo, one of Europe’s most remarkable medieval squares and the stage of the Palio horse race

• Siena Cathedral (Duomo), widely considered one of the most beautiful cathedrals in Italy, with its extraordinary marble decoration, sculpture, and artworks

Your guide will provide context and storytelling that brings these spaces to life, helping you see them not just as monuments, but as living symbols of Siena’s past and present.

The Palio, the Contrade & Siena’s Living Traditions

Siena is not a museum city — it is a place where traditions are still deeply lived. A private tour offers the perfect opportunity to understand the Palio, the famous horse race that has defined Siena’s identity for more than 700 years.

You’ll learn about the contrade (neighborhoods), their symbols, rivalries, and rituals, and how they shape everyday life in the city. This aspect of the tour often becomes one of the most fascinating discoveries for visitors.

A Tour Tailored to Your Interests

Beyond the essential walking tour and Duomo visit, your Siena experience can be fully customized. Depending on your interests, your private tour may also include:

• The Palazzo Pubblico and Civic Museum, home to Siena’s historic government and famous frescoes

• A climb up the Torre del Mangia for sweeping views over the city and countryside

• Lesser-known churches, streets, and corners that reveal Siena’s quieter side

Your guide will help shape the itinerary so that it reflects what you’re most curious about — whether that’s art, history, civic life, or local traditions.

Experience Siena with a Licensed Local Expert

At Travel Italy Guru, we work exclusively with excellent licensed local guides who know Siena deeply and communicate its stories with clarity and passion. Our private tours are designed to be engaging, flexible, and personal, allowing you to experience Siena at your own rhythm.

Whether you’re a history lover, an art enthusiast, or simply eager to experience an authentic Tuscan city, a private tour of Siena offers the depth and insight that group tours simply can’t provide. Contact us for details and a free quote.