Your Siena
from the very first moment

Private experiences with a local host matched to your interests - designed to help you find what matters most & make more of your time in Siena.

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Browse our premium experiences based on your interests.

First Day in Siena: Orientation in the Campo & Beyond City Essentials
Siena

First Day in Siena: Orientation in the Campo & Beyond

5 (62)
2 hours
From   $76.32   per person
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This walk helps you settle into Siena with ease, offering orientation, local insight, and helpful context to begin exploring with confidence.

City Essentials
Siena

Siena Trip Planning Video Call

5 (62)
30-90 minutes
From   $29.5   per person
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Video chat or email with a local to plan your perfect trip or get answers to all your questions

Essential Siena: Famous Sights and Local Secrets Icons & Secrets
Siena

Essential Siena: Famous Sights and Local Secrets

5 (43)
4 hours
From   $127.21   per person
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See the Torre del Mangia, then slip into Siena’s softer side. This walk blends known icons with hidden viewpoints, shaped around your pace.

Siena Your Way: A Personalized 4-Hour Exploration Icons & Secrets
Siena

Siena Your Way: A Personalized 4-Hour Exploration

5 (49)
4 hours
From   $127.21   per person
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Wander quiet lanes or follow the city's rhythm, your host adjusts to your pace, mood, and curiosity in this 4-hour Siena experience.

Secret Siena: Alleys, Oratories & Everyday Rituals Icons & Secrets
Siena

Secret Siena: Alleys, Oratories & Everyday Rituals

5 (54)
3 hours
From   $101.77   per person
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Drift through Siena’s hidden sides, quiet gardens, artisan workshops, and peaceful oratories.

Siena Wine Journey: Tuscan Tastings & Local Delights The Culinary Scene
Siena

Siena Wine Journey: Tuscan Tastings & Local Delights

5 (69)
2 hours
From   $76.32   per person
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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 The Culinary Scene
Siena

Tastes of Siena: Sweet Traditions and Salty Streets

5 (52)
3 hours
From   $140.18   per person
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Explore Siena one bite at a time. This relaxed food walk pairs traditional tastings with local stories and a rhythm shaped by the streets.

Living Siena: Contrade, Craft & Sacred Spaces Stories & Culture
Siena

Living Siena: Contrade, Craft & Sacred Spaces

5 (95)
3 hours
From   $101.77   per person
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Explore Siena's traditions through contrada pride, sacred rituals, and artisan craft, guided by your host and shaped by your interests.

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.

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

Hi, I’m Lillo

Siena
5.0 (3)

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.

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

Languages I speak

  • English
  • French
  • Spanish
  • Italian
  • German

Hi, I’m Stella

Siena
5.0 (4)

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!

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

Languages I speak

  • English
  • Spanish
  • Italian

Hi, I’m Filippo

Siena
4.9 (12)

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!

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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.

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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!

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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.

Visit Host Profile

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.

Visit Host Profile

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

Languages I speak

  • English
  • Italian
  • German

Hi, I’m Letizia

Siena

I love Siena and its magical atmosphere, which I feel every time I arrive in Piazza del Campo. It is a city that has remained authentic, full of hidden corners and breathtaking viewpoints. I am passionate about art, architecture, and history, and I enjoy sharing the stories that make Siena such a unique place. I also love the city’s traditional food, especially artisan gelato and its famous pastry shops, where you can taste local specialties such as ricciarelli and panforte. Join me in Siena if you would like to experience the city in an authentic and unforgettable way!

Visit Host Profile

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

Languages I speak

  • English
  • French
  • Italian
  • German
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Don't Take Our Word For It

Here's what happens when the right host meets the right traveller.

K
Kunj 19 May 2026

Filippo was amazing and very knowledgeable! He made the tour fun and inviting and gave great recommendations for food and shopping as well! We felt as if we saw Siena from a local point of view. Would definitely recommend!

K
Kunj 18 May 2026

Filippo was great! He showed us the city in a very logical way that bended everything together. Great way to see Siena!

L
Linda 18 May 2026

Filippo showed us many different parts of the city with beautiful views. He is very knowledgeable and answered our questions throughly and provided good context. He took care of us, ensuring we had water and bathroom stops as needed.

J
James 8 May 2026

Our guide, Lilly, was fantastic. He was knowledgeable, personable and approachable. We thoroughly enjoyed the tour.

J
Jennifer 30 April 2026

Stella is a gem. What an ocean of knowledge she is. We learned so much, the pace was perfect & we circled back to the spots she shared with us because they were so special. We couldn’t have had a more lovely morning.

J
James 12 April 2026

Lilo was exceptional! He made us feel like family from the beginning and put together an unforgettable day!

M
Meg 9 March 2026

Stella was very personable and knowledgeable of the history of Siena. It was a great 3 hours.

G
Gregory 17 December 2025

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

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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