Discover Siena’s hidden gems with a local guide. Explore medieval streets, secret chapels, and savor wine in secluded spots. Book your personalized tour now.
Discover Siena’s hidden gems with a local guide. Explore medieval streets, secret chapels, and savor wine in secluded spots. Book your personalized tour now.
- Siena - Experience Siena through the perspective of a local who cherishes it—exploring serene lanes, historic squares, neighborhood fountains, and hidden altars. This is not a scripted tour; it’s a flexible, personalized journey tailored to your preferences. Prior to your walk, your host will contact you with a brief questionnaire to learn about…
- Siena - Experience Siena through the perspective of a local who cherishes it—exploring serene lanes, historic squares, neighborhood fountains, and hidden altars. This is not a scripted tour; it’s a flexible, personalized journey tailored to your preferences. Prior to your walk, your host will contact you with a brief questionnaire to learn about your interests—whether you are fascinated by sacred art, medieval architecture, local cuisine, or tranquil viewpoints. Here are some places you might visit:
- Piazza del Campo - Start in Siena’s striking, shell-shaped square—home to the Palio horse race and centuries of civic life. Your host will explain how this iconic space embodies the spirit, rivalry, and unity of Siena’s historic districts.
- Fonte Gaia - Take a moment at this elaborate Renaissance fountain, where sculpted panels once celebrated abundance and innovation. In this hilltop city, Fonte Gaia is more than a monument—it represents survival, pride, and ingenuity.
- Fontebranda - One of Siena’s oldest and most atmospheric fountains. Encircled by medieval stone and arches, it narrates a story of water, survival, and the wool guild that once dominated the area.
- Via di Citta - Walk along this elegant historic street where artisan boutiques and daily life coexist. As locals enjoy their coffee, your host will explain how the street connects the city’s political and cultural core.
- Basilica Cateriniana San Domenico - Enter this solemn 13th-century church, where relics of Saint Catherine provide a profound insight into devotion, mysticism, and Siena’s spiritual essence.
- Ristorante/pizzeria All’Orto de’ Pecci - Escape the cobblestones for this peaceful medieval garden just outside the city walls. Chickens wander, herbs thrive, and Siena’s hustle fades into birdsong—offering an ideal spot to pause and reflect.

- Direct communication with your host for itinerary planning and local recommendations.
- Flexible durations and start times—choose your preferred time when booking.
- Pre-tour questionnaire to tailor the experience to your preferences.
- Private and personalized walking experience with insider tips from a passionate local.
- Direct communication with your host for itinerary planning and local recommendations.
- Flexible durations and start times—choose your preferred time when booking.
- Pre-tour questionnaire to tailor the experience to your preferences.
- Private and personalized walking experience with insider tips from a passionate local.
- Food, drinks and tickets to any attractions
- Transportation (primarily a walking experience, public transport may be used at an additional cost)
- Gratuities (optional)
- Food, drinks and tickets to any attractions
- Transportation (primarily a walking experience, public transport may be used at an additional cost)
- Gratuities (optional)
This walking tour provides an authentic local perspective on Siena, going beyond the typical postcard scenes. Accompanied by your host, you’ll discover hidden chapels, medieval alleyways, serene gardens, and the vibrant traditions of the Palio and contrade. Whether you’re following the trail of a district rivalry, appreciating Gothic architecture, or…
This walking tour provides an authentic local perspective on Siena, going beyond the typical postcard scenes. Accompanied by your host, you’ll discover hidden chapels, medieval alleyways, serene gardens, and the vibrant traditions of the Palio and contrade. Whether you’re following the trail of a district rivalry, appreciating Gothic architecture, or enjoying wine in a secluded enoteca, this is your opportunity to experience Siena like a local, not just a visitor.
Once you book, you’ll receive a brief questionnaire to express your interests and travel preferences. Based on your answers, you’ll be paired with a host who shares your interests and will reach out to propose a tailored itinerary. You’ll agree on a meeting location and time, and your journey can evolve throughout the day based on what piques your curiosity.
- After booking, you’ll receive a short questionnaire to share your interests, preferences, and must-sees. Your guide will personally reach out to craft a fully customized itinerary that suits your style—whether you love history, food, hidden gems, or cultural experiences.
- This private tour is a walking experience. A private vehicle is not included.
- Public transportation or local taxis may be used to transfer between sites. Exact transportation costs can be discussed with your host after your reservation is finalized.
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.