Find your perfect experience!

Quiz intro
Answer a few quick questions, and we'll match you with experiences tailored to your interests, travel style, and how you want to explore.
Start the quiz
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?
Results
Siena experiences!
Based on your travel style, these are our top picks for you.
Best Matches:
Want different results:
Leaving the quiz?
If you leave now before finishing the quiz, your answers will not be saved, finish first?
Save your results to revisit later—without needing to retake the quiz.

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

Top Siena Experiences

Essential Siena: Famous Sights and Local Secrets

Essential Siena: Famous Sights and Local Secrets

$126.13 per person
4 hours

Essential Siena: Famous Sights and Local Secrets

$126.13 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.
See experience
Tastes of Siena: Sweet Traditions and Salty Streets

Tastes of Siena: Sweet Traditions and Salty Streets

$138.98 per person
3 hours

Tastes of Siena: Sweet Traditions and Salty Streets

$138.98 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.
See experience
Siena Your Way: A Personalized 4-Hour Exploration

Siena Your Way: A Personalized 4-Hour Exploration

$126.13 per person
4 hours

Siena Your Way: A Personalized 4-Hour Exploration

$126.13 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.
See experience
Siena Wine Journey: Tuscan Tastings & Local Delights

Siena Wine Journey: Tuscan Tastings & Local Delights

$75.68 per person
2 hours

Siena Wine Journey: Tuscan Tastings & Local Delights

$75.68 per person
2 hours
Discover Siena's authentic wine scene, sampling Tuscan wines with delightful local bites, personalized to your preferences and curiosity.
See experience
Living Siena: Contrade, Craft & Sacred Spaces

Living Siena: Contrade, Craft & Sacred Spaces

$100.9 per person
3 hours

Living Siena: Contrade, Craft & Sacred Spaces

$100.9 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.
See experience

Take the quiz

Find your perfect experience here.
No scripts. No crowds. Just an experience built around you.

More than 25,760 5-star reviews and counting

25,760 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
Click here
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.

$126.13 per person
4 hours
5 (93)
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.

$138.98 per person
3 hours
5 (52)
View more

Real Stories, Real Connections

See our hosts and guests creating memories in Italy
Toasting to Summer with a Fresh Italian Granita

Toasting to Summer with a Fresh Italian Granita

Savoring Simplicity: A Relaxed Italian Snack with Local Flavors

Savoring Simplicity: A Relaxed Italian Snack with Local Flavors

Sunlit Strolls and Warm Hellos on a City Walk

Sunlit Strolls and Warm Hellos on a City Walk

Sunlit Streets and Shared Laughs

Sunlit Streets and Shared Laughs

Friendships Bloom on Italy’s Winding Paths

Friendships Bloom on Italy’s Winding Paths

Family Smiles Under Italy’s Archways

Family Smiles Under Italy’s Archways

Aperitivo Time: Sharing Stories Over Spritz and Snacks

Aperitivo Time: Sharing Stories Over Spritz and Snacks

Discovering Italy’s Charm Together – A Family Day Out

Discovering Italy’s Charm Together – A Family Day Out

A Perfect Afternoon Under the Italian Sky

A Perfect Afternoon Under the Italian Sky

Al Fresco Delight: A Feast of Flavors and Friendship

Al Fresco Delight: A Feast of Flavors and Friendship

Twilight Traditions and Timeless Stories

Twilight Traditions and Timeless Stories

Wandering Timeless Alleys and Making Local Connections

Wandering Timeless Alleys and Making Local Connections

A Slice of Heaven: First Bite of Real Italian Pizza

A Slice of Heaven: First Bite of Real Italian Pizza

Exploring Italy’s Market Magic

Exploring Italy’s Market Magic

Capturing Joy in Every Corner

Capturing Joy in Every Corner

Laughter and Lambrusco at a Cozy Osteria

Laughter and Lambrusco at a Cozy Osteria

Warm Welcome in a Timeless Italian Square

Warm Welcome in a Timeless Italian Square

Laughter and Lambrusco at a Cozy Osteria

Laughter and Lambrusco at a Cozy Osteria

Street Food Stop: Discovering Tigelle with Locals

Street Food Stop: Discovering Tigelle with Locals

A Classic Table, a Homemade Feast

A Classic Table, a Homemade Feast

A Group of Explorers Soaking Up the City’s Energy

A Group of Explorers Soaking Up the City’s Energy

Curious Souls Beneath the Tuscan Sun

Curious Souls Beneath the Tuscan Sun

A Stylish Stroll Through Italian Elegance

A Stylish Stroll Through Italian Elegance

What travelers think of our Italy experiences

Helen Nov 2025

Great!!

Show more
Christoph Oct 2025

Thanks to Filippo for that great day in your city.

Show more
Christoph Oct 2025

Our guide Filippo did lead us to parts of the city, where we would have not gone on our own. He also explained allot about the inhabitants of Siena and their very interesting habits. The tour was perfectly timed and we did see very interesting spots of the city. At the end of the tour he led us to his famous restaurant, where we hat a great lunch. Thanks to Filippo for that great day in your city.

Show more
Cynthia Oct 2025

Lillo was very informative and helpful. He spoke excellent English and gave us a good sense of Siena.

Show more
John Oct 2025

Filippo was a great tour guide. He was very knowledgeable of the culture and history of Siena.

Show more
Michael Oct 2025

Francesco was an excellent to a guide , very personable and informative! His explanations of sites and cultural meanings, made us want to extend our visit in Siena.

Show more
See all reviews

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 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..

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?

Yes! You can blend food, culture, history, neighborhoods, or even a bit of nightlife if time allows. Just share your interests in the questionnaire, and your host will build the day around them.

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.