Icons & Secrets

Woman looking at Siena Cathedral and surrounding buildings.

Tree-lined path on Lucca city walls with people walking in Siena

Person painting a ceramic bowl in a workshop with colorful plates in Sienna

Woman eating a croissant and drinking coffee on a street in Siena

Ice cream held up in a street of in Sienna

Interior of Chiesa di San Giovanni Fuorcivitas in Siena

5 (98)

Secret Siena: Alleys, Oratories & Everyday Rituals

3 hours English

5 (98) 100% Personalized

Drift through Siena’s hidden sides, quiet gardens, artisan workshops, and peaceful oratories.

How It Works

Book your date

Choose your preferred date, start time and group size for your experience.

Share your interests

Complete your personalisation form after booking, for a tailored experience.

Explore with your matched host

We match you with a local host who shapes the route around you.

Experience Overview

Time:

3 hours

What to expect:

Fully tailored to your preferences

Language:

Hosted in English (Other languages may be requested)

Transport Mode:

Walking experience (May use public transport for longer distances)

Meeting point:

Piazza del Mercato, Piazza del Mercato, 53100 Siena SI, Italy

Cancellation:

Free cancellation up to 24 hours before the experience

What’s Included:

Tailored itinerary based on your preferences

A knowledgeable host who knows the hidden gems

Flexible start times to fit your day

What’s Excluded:

Food, drinks and shopping expenses

Transport fares or attraction entry fees

Mostly walking, with food, drinks, transport and entry fees paid separately unless stated.

Reviews of Our Siena Experiences

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!

Margaret

Siena

Letizia was a wonderful guide - we felt like we were being shown Siena by a friend, giving us all the inside tips & telling us the fascinating stories that make Siena special & unique.

Margaret

Siena

Stella had great knowledge about Siena and Italian history. Highly recommend

Elizabeth

Siena

Filippo showed us many different parts of the city with beautiful views. He is very knowledgeable and answered our questions throughly and provided good context. He took care of us, ensuring we had water and bathroom stops as needed.

Linda

Siena

Lilo was exceptional! He made us feel like family from the beginning and put together an unforgettable day!

James

Siena

Nice tour of Siena. Guide was very helpful in telling us about the city.

Douglas

Siena

See all reviews

A possible route, not a fixed script

This sample shows what the experience could include. Your host will shape the route around your interests, pace, weather and plans.

Suggested meeting point

Piazza del Mercato, Piazza del Mercato, 53100 Siena SI, Italy

Forgotten Vicoli & Artisan Traditions

Medieval alleys where craft and quiet routines still live on

Secret Siena: Alleys, Oratories & Everyday Rituals

Wander Siena’s quiet backstreets where time-softened walls and shuttered windows tell everyday stories. You might glimpse a tucked-away workshop or follow your curiosity around the next bend, and your host will shape the path with you.

The Secret Garden of Contrada della Tartuca

A hushed garden tucked behind Tartuca’s contrada walls

Beyond an unmarked arch, a peaceful garden offers shade and calm. Some guests pause to sketch or reflect, others listen to stories of local traditions. Whether still or curious, your host makes space for both.

A Hidden Oratory with Painted Ceilings

An unmarked door hides Siena’s quiet spiritual soul

A small oratory may be open to those who notice it. If so, you’re welcome to step in quietly. Some light a candle, others take in the silence. It’s Siena’s spiritual rhythm, humble, human, and still alive beneath the surface.

Latteria in the Alley

A neighborhood milk bar with ritual, not rush

Your host may bring you to a local latteria, a simple, unpretentious place where mornings move slowly. Whether you try coffee, something sweet, or just soak in the setting, it’s a chance to slip into Siena’s daily rhythm.

Optional Close: Via del Casato View Ledge

A quiet ledge where Siena spreads out in layers

At the end of a hushed street, a stone ledge offers long views over rooftops and distant hills. You might sketch, reflect, or simply take it in. A final quiet moment, letting Siena’s gentler side linger with you a little longer

Siena, Our Guests Way

Here are our guests exploring on a City Unscripted experience.

A Stylish Stroll Through Italian Elegance

Exploring Italy’s Market Magic

Friendships Bloom on Italy’s Winding Paths

Sunlit Streets and Shared Laughs

Family Smiles Under Italy’s Archways

Curious Souls Beneath the Tuscan Sun

Savoring Simplicity: A Relaxed Italian Snack with Local Flavors

Sunlit Strolls and Warm Hellos on a City Walk

Toasting New Friendships with a Taste of Italy

A Group of Explorers Soaking Up the City’s Energy

Wandering Timeless Alleys and Making Local Connections

Capturing Joy in Every Corner

Twilight Traditions and Timeless Stories

Warm Welcome in a Timeless Italian Square

Discovering Italy’s Charm Together – A Family Day Out

A Perfect Afternoon Under the Italian Sky

Your FAQs

Is this a traditional tour or something different?

This isn’t a traditional tour with a fixed script. It’s a fully personalized day shaped around your interests, whether it’s culture, history, neighborhoods, or hidden local spots. Your host is a knowledgeable local, more like a friend showing you their city. It’s flexible, one-on-one, and tailored entirely to you.

How does personalization work?

After booking, you’ll receive a short questionnaire where you can share your interests, travel style, and any must-see spots. Based on that, we’ll match you with a local host who’ll reach out to plan your personalized itinerary.

Will I know my itinerary in advance?

Yes, you will have the opportunity to chat with your host directly and agree on a plan for the day. However, there’s always room for spontaneity and local surprises!

Will I see famous landmarks or just hidden gems?

Both! Your host will take you to iconic sights if you want to see them, but they’ll also introduce you to places and stories most travelers miss.

Can I request specific places or types of stops?

Yes! After booking, you will receive a questionnaire where you can highlight must-visit spots and anything else you’d like to include, and your host will craft your experience around them.

Can I change the meeting place?

Yes, you will be in touch with your host before your experience, and you can agree on a different meeting point with them. Your host can meet you anywhere central that’s convenient.

Can my host meet me at my accommodation?

Hotel meet-ups are available upon request in central areas. If you're staying outside the city, your host will recommend the best meeting spot and guide you with directions.

★★★★★

Nina

21 June 2026

I have worked with City Unscripted in several cities. I love the flexibility when needed and the ability to change the agenda on the fly if something else appeals to me.

Nicola was like a friend showing us the best parts of his city

Norman Graham

Lilia was an excellent guide and made us feel very comfortable. She had us engaged in the tour instead of just standing there spitting out info. We hadnt realized just how much walking and visiting we had done until the end. We explored the whole city area and she gave us great tips on dining and areas to explore more.