Siena

Essential Siena: Famous Sights and Local Secrets

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Iconic Sights & Hidden Gems • 4 hours 5

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Essential Siena: Famous Sights and Local Secrets

See the Torre del Mangia, then slip into Siena’s softer side. This walk blends known icons with hidden viewpoints, shaped around your pace.

What makes this experience special

This experience starts where Siena soars, then flows into quieter corners where daily life unfolds unseen. Your host will guide you through icons and backstreets, adjusting as you go

Key highlights

Begin in Piazza del Campo beneath Siena’s iconic medieval tower
Follow quiet Via di Città toward a hidden archway from Siena’s past
Step into a peaceful oratory or a Contrada museum rich with meaning
End with rooftop views or still backstreets lined with quiet beauty
Choose depth or detours at every stop; this is Siena your way
Hear stories of Palio rivalries, civic pride, and everyday traditions
Experience grandeur and local life without ever leaving the city walls

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

4 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 Campo, Il Campo, 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 Campo, Il Campo, 53100 Siena SI, Italy

Torre del Mangia and Piazza del Campo

Start beneath Siena’s tower, where space and story open wide.

Essential Siena: Famous Sights and Local Secrets

Begin where Siena opens up in perfect harmony. Beneath the Torre del Mangia, take in the shell-shaped Campo and the rhythm of the square. You might step inside the Palazzo courtyard or simply pause and notice the Palio flags fluttering in the breeze.

Via di Città and the Arch of Dreams

A noble street with soft echoes and hidden symbolism.

Leave the crowds behind along this noble street, lined with quiet facades and artisan banners. Your host may point out a weathered fresco or pause at the stone arch once marking Siena’s city limits. It is a street full of echoes and space to wonder.

Oratorio di San Bernardino or Contrada Museum

Siena’s quieter heart lives in these sacred, storied rooms.

This small oratory feels far from the city's buzz, its frescoes offering a soft kind of reverence. If open, a Contrada museum may reveal Siena’s soul—flags, costumes and stories carried by generations. These spaces feel lived in, not displayed.

Fortezza Viewpoint or San Martino Backstreets

Choose a wide view or hush and shadowed local corners.

Choose how to close the loop. One path leads up to old brick ramparts with panoramic views. Another dips into Siena’s most hushed corners, where shutters rattle and footsteps echo. Both offer stillness, in different forms.

Optional Close: A Pause at the Fortress Wall

Linger at the top, where Siena glows in golden silence.

If you climb, linger a little. As the light softens, the Duomo peeks through rooftops and Siena glows with that warm, end-of-day quiet locals love

Real Stories, Real Connections

See our hosts and guests creating memories

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Sunlit Streets and Shared Laughs

Toasting New Friendships with a Taste of Italy

A Relaxed Italian Snack with Local Flavors

Sunlit Strolls and Warm Hellos on a City Walk

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A Group of Explorers Soaking Up the City’s Energy

Capturing Joy in Every Corner

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Wandering Timeless Alleys and Making Local Connections

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Twilight Traditions and Timeless Stories

See what happens when you travel unscripted!

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What travelers think of our Italy experiences

Marita Oct 2025

Filippo made it fantastic! Easy pace, interesting details, personable-we enjoyed it immensely.

Grace Oct 2025

Andrea was a phenomenal guide for our tour in Milan. He took us to all of the major cites in the city as well as some lesser known areas that were beautiful. He was very knowledgeable and answered all of the questions we had with additional information that was relevant but we didn't think to ask.

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.

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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 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.

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!

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.

How much walking is involved?

This depends on the experience, but your host can adjust the pace to suit your comfort level.

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.