Find your perfect experience!

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Answer a few quick questions, and we'll match you with experiences tailored to your interests, travel style, and how you want to explore.
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QUESTION 1
What kind of experience makes a trip unforgettable for you?
QUESTION 2
Who are you traveling with?
QUESTION 3
What is the first thing that you look for when arriving in a new city?
QUESTION 4
How do you want to experience the city’s atmosphere?
QUESTION 5
What kind of local connection excites you most?
QUESTION 6
How much time do you have to explore?
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Siena experiences!
Based on your travel style, these are our top picks for you.
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Experience Siena
Beyond the Guidebooks

See the landmarks you’ve dreamed of, and the corners you didn’t know to look for — all in one personalized day.

FIND YOUR PERFECT EXPERIENCE
Italy

Top Siena Experiences

Essential Siena: Famous Sights and Local Secrets

Essential Siena: Famous Sights and Local Secrets

$127.2 per person
4 hours

Essential Siena: Famous Sights and Local Secrets

$127.2 per person
4 hours
See the Torre del Mangia, then slip into Siena’s softer side. This walk blends known icons with hidden viewpoints, shaped around your pace.
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Tastes of Siena: Sweet Traditions and Salty Streets

Tastes of Siena: Sweet Traditions and Salty Streets

$140.18 per person
3 hours

Tastes of Siena: Sweet Traditions and Salty Streets

$140.18 per person
3 hours
Explore Siena one bite at a time. This relaxed food walk pairs traditional tastings with local stories and a rhythm shaped by the streets.
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Siena Your Way: A Personalized 4-Hour Exploration

Siena Your Way: A Personalized 4-Hour Exploration

$127.2 per person
4 hours

Siena Your Way: A Personalized 4-Hour Exploration

$127.2 per person
4 hours
Wander quiet lanes or follow the city's rhythm, your host adjusts to your pace, mood, and curiosity in this 4-hour Siena experience.
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Siena Wine Journey: Tuscan Tastings & Local Delights

Siena Wine Journey: Tuscan Tastings & Local Delights

$76.32 per person
2 hours

Siena Wine Journey: Tuscan Tastings & Local Delights

$76.32 per person
2 hours
Discover Siena's authentic wine scene, sampling Tuscan wines with delightful local bites, personalized to your preferences and curiosity.
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Living Siena: Contrade, Craft & Sacred Spaces

Living Siena: Contrade, Craft & Sacred Spaces

$101.76 per person
3 hours

Living Siena: Contrade, Craft & Sacred Spaces

$101.76 per person
3 hours
Explore Siena's traditions through contrada pride, sacred rituals, and artisan craft, guided by your host and shaped by your interests.
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Find your perfect experience here.
No scripts. No crowds. Just an experience built around you.

More than 17,500 5-star reviews and counting

17,500+ 5-Star Reviews and Counting

Trusted and recommended by travelers worldwide, including 99% on Google and TripAdvisor.

recommended by 99% of travelers on google
recommended by 99% of travelers on tripadvisor

How Personalization Works

All experiences are tailored to you—choose what excites you most.

Pick Your Experience

Browse and choose an experience that excites you—whether it’s hidden gems, local food, or cultural insights.

Share Your Interests

After booking, answer a few quick questions about your travel style and preferences so we can match you with the perfect host.

Connect & Customize

Chat with your host, discuss your interests, and fine-tune the experience before your adventure begins.
Want a sneak peek? View a sample questionnaire
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VIEW THE STEPS

Our Experiences

From hidden streets to well-known highlights—each one shaped by a local and tailored to you

Show prices based on:
Adults (Aged 13+)
Children (Up to 12 years old)
Essential Siena: Famous Sights and Local Secrets
Iconic Sights & Hidden Gems

Essential Siena: Famous Sights and Local Secrets

See details

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

$127.2 per person
4 hours
5 (41)
Tastes of Siena: Sweet Traditions and Salty Streets
Local Food & Drink Tastings

Tastes of Siena: Sweet Traditions and Salty Streets

See details

Explore Siena one bite at a time. This relaxed food walk pairs traditional tastings with local stories and a rhythm shaped by the streets.

$140.18 per person
3 hours
5 (52)
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Real Stories, Real Connections

See our hosts and guests creating memories in Italy
Exploring Italy’s Market Magic

Exploring Italy’s Market Magic

Sunlit Streets and Shared Laughs

Sunlit Streets and Shared Laughs

Friendships Bloom on Italy’s Winding Paths

Friendships Bloom on Italy’s Winding Paths

A Stylish Stroll Through Italian Elegance

A Stylish Stroll Through Italian Elegance

Curious Souls Beneath the Tuscan Sun

Curious Souls Beneath the Tuscan Sun

Sunlit Strolls and Warm Hellos on a City Walk

Sunlit Strolls and Warm Hellos on a City Walk

Family Smiles Under Italy’s Archways

Family Smiles Under Italy’s Archways

A Perfect Afternoon Under the Italian Sky

A Perfect Afternoon Under the Italian Sky

A Group of Explorers Soaking Up the City’s Energy

A Group of Explorers Soaking Up the City’s Energy

Wandering Timeless Alleys and Making Local Connections

Wandering Timeless Alleys and Making Local Connections

Capturing Joy in Every Corner

Capturing Joy in Every Corner

Warm Welcome in a Timeless Italian Square

Warm Welcome in a Timeless Italian Square

Twilight Traditions and Timeless Stories

Twilight Traditions and Timeless Stories

Discovering Italy’s Charm Together – A Family Day Out

Discovering Italy’s Charm Together – A Family Day Out

Laughter and Lambrusco at a Cozy Osteria

Laughter and Lambrusco at a Cozy Osteria

Savoring Simplicity: A Relaxed Italian Snack with Local Flavors

Savoring Simplicity: A Relaxed Italian Snack with Local Flavors

Aperitivo Time: Sharing Stories Over Spritz and Snacks

Aperitivo Time: Sharing Stories Over Spritz and Snacks

Street Food Stop: Discovering Tigelle with Locals

Street Food Stop: Discovering Tigelle with Locals

A Slice of Heaven: First Bite of Real Italian Pizza

A Slice of Heaven: First Bite of Real Italian Pizza

Al Fresco Delight: A Feast of Flavors and Friendship

Al Fresco Delight: A Feast of Flavors and Friendship

Laughter and Lambrusco at a Cozy Osteria

Laughter and Lambrusco at a Cozy Osteria

Toasting to Summer with a Fresh Italian Granita

Toasting to Summer with a Fresh Italian Granita

A Classic Table, a Homemade Feast

A Classic Table, a Homemade Feast

What travelers think of our Italy experiences

Beverly Aug 2025

We loved being guided through the various neighborhoods, some of which we probably would not have ventured to on our own.

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Jennifer Aug 2025

Great!

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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.

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Marc Aug 2025

My parents and I did a 3 hour tour with Daniela. It was fantastic. She showed us a ton of cool stuff and gave us a completely new appreciation for Naples. She was incredibly knowledgeable, and answered a ton of our questions to include specific dates, locations and explaining what we were seeing. Daniela's English was excellent, she was exactly on time, and she was flexible showing us what we wanted to see. I highly recommend doing a tour with her.

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Mary Aug 2025

Great tour, enjoyed our time. Family friendly and our guide was accommodating with the heat making sure we mostly stayed in the shade:) She was also great with communication.

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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

Are experiences the same as tours?

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.

What if I don’t know what I want to explore?

That’s completely fine! Select an experience theme or a flexible discovery experience, and after booking, answer a few questions so your host can design the perfect experience for you.

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.

How do you match me with a host?

We ask a few questions. After you book, you’ll fill out a short questionnaire about your interests and travel style. We’ll then match you with the best local host to design your experience.

Can I mix different themes in one experience?

Absolutely! Whether you want a blend of food, history, local culture, or nightlife, your host will seamlessly weave them together into one immersive experience.

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 cancel if my plans change?

Yes. You can cancel for free up to 24 hours before your experience date—no questions asked.