Siena

Secret Siena: Alleys, Oratories & Everyday Rituals

Hidden Gems • 3 hours 5

(34)

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

Ricky Jun 2025

Our guide (Daniela) was extremely knowledgeable about the sights and historical places of Naples. She was accommodating to our interests- best place for gelato and pastries the shopping area, the Spanish quarter. It was an extremely hot day but we weren’t rushed, it was our tour and Dan was so accommodating. On reflection it was great value for money as we saw lots and learnt lots about the fantastic Naples, the culture and history. Truly fascinating city.

June 2025

Our guide, Martina, was extremely knowledgeable and gave us just the right amount of history/facts about all the sites we were seeing. Loved that she tailored the tour exactly to our needs and wants. Great experience. Thank you Martina!

David Jun 2025

Serena was our guide and she made the tour fantastic from beginning to end. She tailored it to our needs and was so knowledgeable. We sample the local food, heard about local culture and history. Serena’s passion for Napoli was infectious. We would highly recommend, even to teeenagers..our 14 and 16 year old loved it.

June 2025

The local insights of Onofrio gave us another view on many aspects of the city

Henry Jun 2025

The tour was everything we expected and more. Roberto was an excellent tour and host to the city of Naples. With Roberto we were able to learn about the history and authentic tastes of the city. Highly recommended.

June 2025

Benedetta met us at our hotel for a four-hour private walking tour of Venice. As a local (born and bred) Benedetta displayed a great deal of knowledge of the history and culture of Venice. We ambled around going where we wanted and seeing more besides. We’d opted for this tour on Day 1 of our trip, primarily to source inside knowledge of the sights to visit, how to avoid the queues and the best locations to eat/drink and take a ‘romantic’ Gondola ride. That evening we ate at a fantastic seafood restaurant (Al Colombo) in the quiet back-streets close to Rialto Bridge. The following day, we took Benedetta’s advice and headed to the quieter Jewish Quarter (Cannaregio) after a lovely Gondola ride in San Toma area. This tour was an excellent way to see the city at an easy pace and gain an insider’s knowledge of the city and its sights. Thoroughly recommended!

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FAQs

Your questions, answered

Is this a traditional tour?

No. Our experiences are unscripted and designed around you. Instead of following a rigid itinerary, your host will plan a personalized journey that feels natural, immersive, and unique.

How does personalization work?

After booking, you’ll complete a short questionnaire about your interests and travel style. We’ll match you with the best host who will tailor the experience to you. You'll have the opportunity to chat with them before the experience and agree on a plan.

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 to visit?

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.