Siena Tours and Experiences

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Siena Walking Tours

Siena Private Tour Guides


In the heart of Tuscany, where the sun-baked hills cradle a city of timeless beauty, lies Siena, a gem whose medieval soul still beats vigorously beneath its ancient stones. Here, history isn't just remembered; it's lived, with every street corner and piazza offering a glimpse into a bygone era.

Embark on a Siena walking tour that serves as your portal to this medieval marvel. Our Introduction to Siena Tour with the Duomo introduces you to the city's core, guided by the insightful narratives of our Siena private tour guides. As you traverse the narrow, winding streets, you'll stand in awe of the Siena Cathedral, its black and white marble façade telling tales of faith and artistry. Inside, the Duomo's interior, a symphony of Gothic and Romanesque styles, unfolds like the pages of a sacred text, each fresco and sculpture a chapter in Siena's rich cultural history.

But Siena's spirit truly comes alive during our Siena Palio Tour. This experience immerses you in the fervor of one of the world's oldest horse races, held in the iconic Piazza del Campo. Here, the city divides into its Contrade, each district a heartbeat of pride and rivalry. Your guide, a custodian of this tradition, will unveil the complexities of this medieval spectacle, where the race is but a moment in a year-long saga of community and competition. The tour not only brings you to the edge of the race but also to the heart of what it means to be Sienese.

For those whose palate yearns for the taste of Tuscany, the Full-Day Tuscany Day Trip from Siena with Wine Tasting is an odyssey through the Val d'Orcia, a landscape that has inspired poets and painters. In the company of an expert local guide, you'll explore vineyards where the earth's gifts are transformed into liquid gold. The journey includes visits to historic wineries, where you'll learn the art of winemaking, savor the bold Chianti and the velvety Brunello, and understand how the land's character is captured in every glass.

Siena isn't merely a city; it's a living museum where every step is a lesson in history, every sip a taste of tradition, and every moment a connection to the past. Whether you're wandering through its medieval streets, feeling the adrenaline of the Palio, or tasting the essence of Tuscany, Siena invites you to become part of its enduring story. 
What Context Siena Travelers Say
(4.81) 121 Reviews

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Stella was a wonderful guide. She knew the area well and showed up some fabulous sights. Wine tasting was fun, and we learned so much. Thanks for a fantastic experience Stella!
Stella did an extraordinary job with her introduction to Siena, and was able to tailor her approach to a 10-year-old's attention span. She also added a surprise visit to an Etruscan tomb that had been discovered in a wine store. We found this to be a fascinating insight into Italian history.
Stella is a great tour guide. Her love for Siena shined through as she showed us around. We truly enjoyed our time with her and hearing all the interesting things about Siena.
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