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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Curious Souls Beneath the Tuscan Sun

A Stylish Stroll Through Italian Elegance

Friendships Bloom on Italy’s Winding Paths

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

Family Smiles Under Italy’s Archways

A Group of Explorers Soaking Up the City’s Energy

Capturing Joy in Every Corner

A Perfect Afternoon Under the Italian Sky

Wandering Timeless Alleys and Making Local Connections

Discovering Italy’s Charm Together – A Family Day Out

Twilight Traditions and Timeless Stories

See what happens when you travel unscripted!

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What travelers think of our Italy experiences

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.

Daniel Aug 2025

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.

Elina Aug 2025

We had a fantastic time with our tour guide Bibi. She got in touch with us before our arrival to customize our experience. From the second we met her, we knew we were very fortunate to have a tour from a local. She knew every street, every corner, every restaurant and bar. We saw everything that we planned to see and more. I highly recommend Bibi if you want to tour like a local

Jennifer Aug 2025

Our guide (Donatella) was absolutely amazing. We had people between the ages of 60 and 16 and everyone loved our tour. We experienced the local food as well as saw really cool sites. Would recommend this tour to anyone.

Anthony Aug 2025

Donatella was incredible! She made us feel like home in Naples. She showed us so much of the city, gave us fascinating history and we had great conversation!

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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 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.