Personalized Siena
Experiences, Without Scripts

Not just a tour, no scripts. Just the city, done properly and shaped around you. Choose your category, pick your depth & we will match you with a local host.

Find your perfect experience

Top Siena Experiences

Essential Siena: Famous Sights and Local Secrets

Essential Siena: Famous Sights and Local Secrets

$126.13 p.p.
4 hours

Essential Siena: Famous Sights and Local Secrets

$126.13 p.p.
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 p.p.
3 hours

Tastes of Siena: Sweet Traditions and Salty Streets

$138.98 p.p.
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 p.p.
4 hours

Siena Your Way: A Personalized 4-Hour Exploration

$126.13 p.p.
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

$75.68 p.p.
2 hours

Siena Wine Journey: Tuscan Tastings & Local Delights

$75.68 p.p.
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 p.p.
3 hours

Living Siena: Contrade, Craft & Sacred Spaces

$100.9 p.p.
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.

How Personalization Works

Every experience is private and tailored to you. Here’s how it works.

Choose a flexible experience

Whether it’s the must-sees or the unexpected, your day is designed around what matters to you.

Tell us what you’re into

Love food? Culture? Quiet streets? We’ll shape the day around what you’re curious to discover.

Meet your host and shape your day

Our hosts share stories, not scripts; it’s like exploring a city with someone who truly lives it.

Explore more of Iconic Sights & Hidden Gems

Here are some of our top experiences for Iconic Sights & Hidden Gems across the world.

Essential Siena: Famous Sights and Local Secrets Iconic Sights & Hidden Gems
Siena

Essential Siena: Famous Sights and Local Secrets

5 (43)
4 hours
From   $126.13   per person
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.

Explore more of Local Food & Drink Tastings

Here are some of our top experiences for Local Food & Drink Tastings across the world.

Siena Wine Journey: Tuscan Tastings & Local Delights Local Food & Drink Tastings
Siena

Siena Wine Journey: Tuscan Tastings & Local Delights

5 (69)
2 hours
From   $75.68   per person
See details

Discover Siena's authentic wine scene, sampling Tuscan wines with delightful local bites, personalized to your preferences and curiosity.

Tastes of Siena: Sweet Traditions and Salty Streets Local Food & Drink Tastings
Siena

Tastes of Siena: Sweet Traditions and Salty Streets

5 (52)
3 hours
From   $138.98   per person
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.

More than 27,063 5-star reviews and counting

27,063+ 5-Star Reviews and Counting

Trusted and recommended by travelers worldwide.

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

Our Experiences

Every Experience is Designed Around 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
Siena

Essential Siena: Famous Sights and Local Secrets

5 (43)
4 hours
From   $126.13   per person
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.

Tastes of Siena: Sweet Traditions and Salty Streets Local Food & Drink Tastings
Siena

Tastes of Siena: Sweet Traditions and Salty Streets

5 (52)
3 hours
From   $138.98   per person
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.

Siena Wine Journey: Tuscan Tastings & Local Delights Local Food & Drink Tastings
Siena

Siena Wine Journey: Tuscan Tastings & Local Delights

5 (69)
2 hours
From   $75.68   per person
See details

Discover Siena's authentic wine scene, sampling Tuscan wines with delightful local bites, personalized to your preferences and curiosity.

View more

Hi, I’m Lillo

Siena
5.0 (1)

I'm Lillo – a local host in the beautiful city of Siena. What I love most here is the deep sense of tradition, the peaceful atmosphere, and the stunning landscapes all around. I spend my free time walking through the historic center, tasting local specialties, and soaking in the unique spirit of the Contradas. I know the Antiporto area and the neighborhoods around the train station like a local - because I am one! With a passion for food, drinks, and the stories that bring Siena to life, I’m excited to share the flavors and traditions of this magical city with you.

Here’s how I can help make your experience unique.

Languages I speak

  • English
  • French
  • Spanish
  • Italian
  • German

Hi, I’m Grazia

Siena

What I love most about this city is everything connected to the Palio, its incredible architecture, and of course, a big plate of pici. You’ll often find me enjoying a gelato while strolling through the city center or discovering a new favorite restaurant tucked away in San Miniato. I know Siena’s traditions inside out – especially the Palio and the stories that bring each Contrada to life. If you're ready to dive into local food, culture, and history, I can't wait to show you the Siena I know and love!

Here’s how I can help make your experience unique.

Languages I speak

  • English
  • French
  • Spanish
  • Italian

Hi, I’m Stella

Siena
5.0 (2)

I’m Stella – a proud local who loves Siena with all my heart (and stomach!). Whether I’m strolling through the historic streets, chatting with neighbours, or cheering at the Palio, I soak up the city’s energy and traditions every day. I know every corner of Siena, especially my beloved district, La Torre, where the social life is as rich as the wine. I never tire of visiting the Cathedral, exploring museums, or enjoying evenings in Piazza del Campo with friends. If you're looking to experience the real Siena - its food, its stories, its soul - I'm here to share it all with you, one joyful step at a time!

Here’s how I can help make your experience unique.

Languages I speak

  • English
  • Spanish
  • Italian

Hi, I’m Francesco

Siena
5.0 (2)

What excites me most about this city is the Palio - a 600-year-old horse race that’s much more than a race; it’s the heartbeat of Siena’s 17 family-like Contrade. Beyond the city walls, the province offers UNESCO treasures, stunning landscapes in Val d’Orcia, and the Chianti wine region. I love Siena’s medieval charm, its honest, hearty Tuscan food, and the warm spirit of conviviality. Whether you want practical tips, hidden scenic spots, or cultural gems like museums and theaters, I’m here to make your experience unforgettable!

Here’s how I can help make your experience unique.

Languages I speak

  • English
  • Spanish
  • Italian

Hi, I’m Filippo

Siena
4.9 (9)

I’m Phil, your local host in Siena. I’m passionate about the city’s winding red-brick streets, where the light plays beautifully between buildings and every corner tells a story. I love discovering hidden gems and spotting unique views - just look up and Siena will surprise you! I know the entire city centre inside the walls, from the majestic Dome and Baptistry to the lively contrada districts. I’m especially drawn to the deep history and culture tied to Siena’s churches and how they shaped the people. The Palio, the food, the traditions - there’s nothing quite like it. Let me show you the soul of Siena, one secret spot at a time!

Here’s how I can help make your experience unique.

Languages I speak

  • English
  • Spanish

Hi, I’m Francesca

Siena

I adore spending time in the historic center, where every corner tells a story. With a strong background in the food and beverage industry, I also enjoy guiding guests through Siena’s authentic restaurants and lively markets, where our culinary traditions come to life. As a storyteller at heart, I focus on bringing the city’s churches, museums, and medieval and Renaissance heritage to life in a way that feels both engaging and memorable. With me, you’ll experience Siena not just as a visitor, but as part of its living history.

Here’s how I can help make your experience unique.

Languages I speak

  • English
  • Spanish
  • Italian

Hi, I’m Ale

Siena

What I adore most about Siena is the deep sense of belonging that comes from being part of a Contrada - it’s like having a second family, full of devotion, joy, and tradition. I live in the Nicchio neighborhood and know the city’s historic squares by heart, from Piazza del Campo to the Duomo. My favorite moments are having breakfast on Via di Città on a quiet Sunday and feeling the excitement build during the week of the Palio - especially during the magical night rehearsals. I’m passionate about our traditions, food, and the unique energy that makes Siena unforgettable. I can’t wait to share its stories, flavors, and secrets with you!

Here’s how I can help make your experience unique.

Languages I speak

  • English
  • Spanish
  • Italian
  • Portuguese
  • German

Hi, I’m Giamma

Siena

I’m endlessly fascinated by the Palio and the life of the neighborhoods, where pride and community thrive. As a certified olive oil sommelier and wine student, I enjoy introducing guests to Tuscany’s authentic flavors - from rustic ciaccini to a perfect glass of Chianti. Whether we’re exploring secret courtyards, uncovering stories of medieval rivalries, or relaxing at my favorite local bar, I aim to make every experience feel warm, personal and deeply Sienese.

Here’s how I can help make your experience unique.

Languages I speak

  • English
  • French
  • Spanish
  • Italian
  • German

Hi, I’m Silvia

Siena

What I love most about Siena is the intact medieval atmosphere you feel as you wander through its streets and squares. The Palio and the contrade are the true soul of the town, strong and genuine traditions that make Siena unique in the world. I’m especially passionate about the Cathedral, Piazza del Campo, and the city’s incredible art treasures. I’ve lived in Siena’s historic center for years and have been guiding in Tuscany for almost 20 years as both a city and nature guide. I love walking in nature, discovering new trails, enjoying picnics with views over the Tuscan countryside, and getting lost in the breathtaking panoramas of the surrounding hills. I know Siena and its province, San Gimignano, Volterra, Chianti, Val d’Orcia, Pienza, Montepulciano, and the Brunello di Montalcino area very well. As a food and wine lover, I can introduce you to family-run wineries and farms where you can meet the owners themselves. I’m also a mother, and I know how to make experiences engaging and fun for children too. I can’t wait to share the beauty, flavors, and traditions of Siena with you.

Here’s how I can help make your experience unique.

Languages I speak

  • English
  • Italian
  • German

What travelers think of our Italy experiences

G
Gregory 17 December 2025

Filippo was professional, knowledgeable, and attentive to us. He was engaging and easy to be around

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H
Helen 1 November 2025

Great!!

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C
Christoph 22 October 2025

Thanks to Filippo for that great day in your city.

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C
Christoph 22 October 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.

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C
Cynthia 14 October 2025

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

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J
John 13 October 2025

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

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M
Michael 8 October 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.

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L
Layne 6 October 2025

A private tour specialized to our interests and be an amazing local guide. We would not have learned to much about the city without Francesco as our guide. It was wonderful.

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Real Stories, Real Connections

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

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.
City Unscripted

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