This walking tour offers a truly local take on Siena, far beyond the postcard views. With your host, you’ll explore hidden chapels, medieval backstreets, peaceful gardens, and the living traditions of the Palio and contrade. Whether you're tracing the path of a district rivalry, admiring Gothic architecture, or sipping wine in a tucked-away enoteca, this is your chance to explore like a local, not a tourist.
After booking, you’ll receive a short questionnaire to share your interests and travel style. Based on your responses, you’ll be matched with a like-minded host who will contact you directly to suggest a personalized itinerary. You’ll agree on a meeting point and time, and your route can adapt throughout the day based on what captures your interest.
This is a private walking tour. Your host will meet you at your chosen hotel, or you can select the central meeting point instead, which we recommend for the best overall experience. If your hotel isn’t listed, please choose the central landmark option. No private vehicle is included.
This is a private walking tour. Your host will meet you at your chosen hotel, or you can select the central meeting point instead, which we recommend for the best overall experience. If your hotel isn’t listed, please choose the central landmark option. No private vehicle is included.
See Siena through the eyes of someone who lives and loves it—wandering quiet lanes, historic squares, neighborhood fountains, and hidden altars. This isn’t a scripted tour; it’s a flexible, personalized experience shaped around you. Before your walk, your host will reach out with a short questionnaire to understand your interests—whether you're drawn to sacred art, medieval architecture, local food, or peaceful viewpoints. Here are some places you might explore:
Begin in Siena’s dramatic, shell-shaped square—home to the Palio horse race and centuries of civic life. Your host will share how this iconic space captures the spirit, rivalry, and unity of Siena’s historic districts.
Pause at this ornate Renaissance fountain, where sculpted panels once celebrated abundance and innovation. In a hilltop city, Fonte Gaia is more than a monument—it’s a symbol of survival, pride, and ingenuity.
One of Siena’s oldest and most atmospheric fountains. Surrounded by medieval stone and arches, it tells a story of water, survival, and the wool guild that once ruled the area.
Stroll this refined historic street where artisan boutiques and daily life flow side by side. As locals linger over coffee, your host will share how the street links the city’s political and cultural heart.
Step into this solemn 13th-century church, where relics of Saint Catherine offer a powerful glimpse into devotion, mysticism, and Siena’s spiritual identity.
Leave the cobblestones behind for this tranquil medieval garden just beyond the city walls. Chickens roam, herbs flourish, and Siena’s bustle fades into birdsong—offering a perfect place to pause and reflect.
For a full refund, cancel at least 24 hours before the scheduled departure time.
You can cancel up to 24 hours in advance of the experience for a full refund.
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