Siena Private Highlights and Hidden Gems Walking Tour

4.9 (15 reviews) 2–6 hours Free cancellation Private tour

out of 5

15 reviews

4.9

Siena Private Highlights and Hidden Gems Walking Tour — Photos: the activity supplier, via Viator

Siena Private Highlights and Hidden Gems Walking Tour, photo 2 — Photos: the activity supplier, via Viator

About this activity

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 online Personalization Form 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.

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At a glance

Duration: 2–6 hours
Confirmation: Instant confirmation
Ticket: Mobile or paper ticket accepted
Group: Your group only
People per booking: 1–8
Guide: English, Italian
Operated by: City Unscripted

Ages: Adults (0–99 years)

What is included

Included

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

Not included

Not included: Food, drinks and tickets to any attractions
Not included: Transportation (primarily a walking experience, public transport may be used at an additional cost)
Not included: Gratuities (optional)
Not included: Hotel drop off

Itinerary

Siena

Passing by

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 online Personalization Form 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:
Piazza del Campo

Passing by

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.
Fonte Gaia

Passing by

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.
Fontebranda

Passing by

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.
Via di Citta

Passing by

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.
Stop 6

Passing by

Step into this solemn 13th-century church, where relics of Saint Catherine offer a powerful glimpse into devotion, mysticism, and Siena’s spiritual identity.
Stop 7

Passing by

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.

Meeting point and pickup

You can be picked up from your accommodation or go straight to the meeting point.

Meeting point

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 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.

Pickup points

Villa Elda Boutique Hotel
Hotel Palazzo dei Priori
Hotel Palazzetto Rosso
Hotel Duomo
Albergo Cannon d'Oro
Hotel Tre Donzelle
Hotel Italia
Hotel Minerva
Grand Hotel Continental Siena - Starhotels Collezione
Hotel Santa Caterina
NH Siena
Hotel Il Giardino di SIENA

and 15 more pickup points

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.

Using your ticket

Once you've booked your experience, your local host will personally reach out to tailor the adventure to your interests. Whether you're seeking authentic food spots, cultural insights, or hidden gems, we ensure your journey is immersive, personalized, and uniquely yours, transforming your tour into a meaningful connection with the city.

Cancellation

Free cancellation

For a full refund, cancel at least 24 hours before the scheduled departure time.

If you cancel	You get back
At least one day before	100%
Less than a day before	0%

Good to know

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 Personalization Form 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.