Siena

Secret Siena: Alleys, Oratories & Everyday Rituals

Hidden Gems • 3 hours 5

(54)

Secret Siena: Alleys, Oratories & Everyday Rituals

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

What makes this experience special

You’ll explore Siena’s lesser-seen side, textured, tranquil, and steeped in tradition, with a host who adapts every moment to your pace and curiosity.

Key highlights

Wander alleys only locals use, far from the tourist trail
Pause in a hidden garden, fluttering with Palio flags
Reflect beneath painted ceilings in a secret oratory
Maybe taste warm ricotta and espresso where locals gather
Linger at a rooftop ledge, many never find
Personalize each stop, stay, sketch, or stroll onward

What to know before you go

Here’s everything you need to know before your day unfolds.

At a glance What’s included Things to know

3 hours

Fully tailored to your preferences

English Other languages may be requested

Walking experience may use public transport for long distances

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 not included

Food, drinks and shopping expenses

Transport fares or attraction entry fees

Meeting point

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

Cancellation

Free cancellation up to 24 hours before the experience

What to bring

How your day could unfold

A flexible, unscripted experience designed entirely around your interests. Your host will adapt the day based on what excites you most

Here’s what your experience could look like

These are just suggestions from our hosts to inspire your day. Your host will tailor the experience to suit your interests and tastes

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

Real Stories, Real Connections

See our hosts and guests creating memories

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

See what happens when you travel unscripted!

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What travelers think of our Italy experiences

Lisa Sep 2025

Roberto was so knowledgeable and passionate about his Napoli! He found us, which I really appreciated and he took us to all sorts of interesting places and had lots of stories and history to share. I highly recommend this tour with Roberto.

Elmar Sep 2025

Great!

Elmar Sep 2025

The profound explanations about the historically different districts, their social functions which are so specific and unique in Siena and the Palio as part of these traditions still fully alive in Siena.

Richard H 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.

Richard H Aug 2025

Stella was wonderful very knowledgeable and very patient with us asking many questions. She was friendly and cheerful and we had a few good laughs. She was also very knowledgeable and explaining the different flags and the colors and their meetings in this legendary horse race. She did a wonderful job. She went over and above, made our day. Thank you.

Douglas Oct 2025

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

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FAQs

Your questions, answered

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.