Siena Private Highlights and Hidden Gems Walking Tour
Description
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.
Tour Options
Itinerary
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.
Highlights
What's included
Pickup Locations & Times
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.
Traveller Ratings
Important Information
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- This is a private City Unscripted experience: real people, real connections
- After booking, you'll receive a short online questionnaire to share your interests, preferences, and must-sees. Your City Unscripted 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.
Reviews(7)
Amazing experience. Letizia was very knowledgeable and helpful in Sienna. Would highly recommend. Great tour and would most definitely do it again.
We're thrilled to hear you had such an amazing experience in Siena. It’s wonderful to know you left with a deeper appreciation of the city and memories worth repeating. Thank you for your recommendation — we'd love to welcome you back for another experience in the future.
Letizia was a wonderful guide - it was like having a friend show us all the secrets of Siena. Perfectly paced, not strenuous - 3 hours went quickly, then at the end we could go into the Duomo by ourselves - wow!
We're delighted to hear that Letizia made you feel as though you were exploring the city with a friend and that she was able to share the hidden stories and secrets of Siena in such an engaging way. It's also great to know that the pace of the experience was comfortable and enjoyable, and that the three hours flew by.
Filippo was amazing and very knowledgeable! He made the tour fun and inviting and gave great recommendations for food and shopping as well! We felt as if we saw Siena from a local point of view. Would definitely recommend!
We’re so delighted that you had such a wonderful experience with Filippo! Thank you for your kind words about his knowledge, recommendations, and welcoming approach. It’s fantastic to know that you were able to experience Siena from a true local perspective. We truly appreciate your recommendation and hope to assist you again in your future travels.
Stella is a gem. What an ocean of knowledge she is. We learned so much, the pace was perfect & we circled back to the spots she shared with us because they were so special. We couldn’t have had a more lovely morning.
We’re so glad you had such a lovely and memorable morning exploring at the perfect pace! It’s wonderful to hear how much stayed with you — thank you for sharing this.
Lillo was very informative and helpful. He spoke excellent English and gave us a good sense of Siena.
We’re so happy to hear you enjoyed your time in Siena with Lillo! It’s wonderful that his knowledge and clear communication made the experience so enjoyable. Thank you for your kind feedback!
A private tour specialized to our interests and be an amazing local guide. We would not have learned to much about the city without Francesco as our guide. It was wonderful.
Thank you for sharing your experience! We’re delighted to hear that Francesco made your private experience so engaging and tailored to your interests. His expertise and local knowledge clearly helped you discover and learn so much about the city that you might have missed on your own. It sounds like the tour was both informative and memorable, making your visit extra special.
Our tour was exceptional. Stella was outstanding. We gained a significant amount of knowledge from Stella and she was delightful to be around. This beautiful city is steeped in history. Stella also provided insight into the origins of the Horse Race and we witnessed immense pride among the people involved. Furthermore, Stella went above and beyond to ensure we located the meeting point, as it was our first time driving in Italy, and she also assisted us in finding our way back to the parking area. Her helpfulness was greatly appreciated.
We’re so glad to hear your experience with Stella was exceptional. It’s wonderful that her knowledge, warmth, and extra care made your time in Italy so memorable and seamless from start to finish. Thank you for sharing such kind feedback!
