Siena Private Highlights and Hidden Gems Walking Tour

Siena, Italy

Popular pick

Booked 5+ times last week!

2 to 6 hours (approx.)
Pickup offered
Group discounts
Mobile ticket
Offered in: English

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Overview

Siena is one of Tuscany's most fascinating hill towns, but most visitors check off a handful of famous sights and move on. Get a more in-depth, personalized introduction to this medieval city on this private walking tour, fully customized to your pace and interests. Focus on the historic architecture, traditional Palio festival, or local food scene, or combine culture and cuisine to create a unique itinerary. Choose an express tour of just a few hours or a full-day deep dive that takes you to little-known gems most tourists miss.

A private tour created to match your interests and travel style
Choose a tour duration that fits your schedule, from two hours to a full day
Pick up insider tips and recommendations from your local guide
Begin your tour at the time you choose to make the most of your day

What's Included

Private and personalized walking experience with insider tips from a passionate local
Online questionnaire link sent after booking to tailor your experience and match you to a local host
Get picked up (on foot) at your accommodation if it's central
Flexible durations and start times - Pick your preferred duration when you book
Direct communication with your host for itinerary planning and local recommendations

Food, drinks and tickets to any attractions
Transportation (primarily a walking experience, public transport may be used at an additional cost)
Gratuities (optional)
Hotel drop off

Meeting and Pickup

You can head directly to the meeting point, or request pickup

Pickup points

Select a pickup point

Pickup details

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.

Meeting point

Piazza del Campo
Il Campo, 53100 Siena SI, Italy
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.

End point

This activity ends back at the meeting point.

Itinerary

Siena (Pass By)

Piazza del Campo (Pass By)

Fonte Gaia (Pass By)

Fontebranda (Pass By)

Via di Citta (Pass By)

Basilica Cateriniana di San Domenico (Pass By)

Ristorante/pizzeria All'Orto de' Pecci (Pass By)

Additional Info

Confirmation will be received at time of booking
Wheelchair accessible
Stroller accessible
Service animals allowed
Near public transportation
Most travelers can participate

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.
This is a private tour/activity. Only your group will participate

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Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Reviews

5.0

based on 8 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Informative and pleasant.

Royal_J, Jul 2026

The information was amazing. We learned a lot about things that were of interest to us. Stella was very pleasant. Take lots of pictures of the landmarks she points out if you are staying in town to walk around more on your own. The pacing was perfect.

Response from Host, Jul 2026

We're so glad you enjoyed such a well-paced and informative experience. It’s wonderful to hear it focused on the things that interested you most and gave you plenty of inspiration for exploring even more on your own. Thank you for sharing your kind feedback — we're delighted this was such a memorable part of your trip.

Amazing experience....

Joshua_N, Jun 2026

Amazing experience. Letizia was very knowledgeable and helpful in Sienna. Would highly recommend. Great tour and would most definitely do it again.

Response from Host, Jun 2026

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.

Great way to see Siena

Margaret_S, Jun 2026

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!

Response from Host, Jun 2026

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...

Kunj_P, May 2026

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!

Response from Host, May 2026

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.

Lillo was very...

Cynthia_M, Oct 2025

Lillo was very informative and helpful. He spoke excellent English and gave us a good sense of Siena.

Response from Host, Oct 2025

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!

Amazing Experience

Layne_S, Oct 2025

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.

Response from Host, Oct 2025

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.

Best tour ever .Our tour was amazing. Stella was wonderful.We learned so much from Stella and she was so much fun

RichardH_M, Aug 2025

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.

Response from Host, Aug 2025

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!