Private Siena
experiences with a local host chosen for you

Tell us your interests, we'll match you with the right Siena local

Explore Siena Experiences

How your experience becomes personal

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

Choose your category & experience

Browse our categories & experiences based on your interests and plans.

Personalize after booking

Answer a few questions about your interests, pace, plans, to personalize.

Meet your matched host

Your host gets in touch before hand to shape the experience around you.

Explore by Category

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

First Day in Siena: Orientation in the Campo & Beyond

5 (33)
2 hours
From   $73.74   per person
See details

This walk helps you settle into Siena with ease, offering orientation, local insight, and helpful context to begin exploring with confidence.

Snapshot
First Day Essentials
Siena

Siena Trip Planning Video Call

5 (62)
30-90 minutes
From   $28.5   per person
See details

Video chat or email with a local to plan your perfect trip or get answers to all your questions

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

Essential Siena: Famous Sights and Local Secrets

5 (30)
4 hours
From   $122.89   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
Siena Your Way: A Personalized 4-Hour Exploration Icons & Secrets
Siena

Siena Your Way: A Personalized 4-Hour Exploration

4.9 (40)
4 hours
From   $122.89   per person
See details

Wander quiet lanes or follow the city's rhythm, your host adjusts to your pace, mood, and curiosity in this 4-hour Siena experience.

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

Secret Siena: Alleys, Oratories & Everyday Rituals

4.9 (42)
3 hours
From   $98.32   per person
See details

Drift through Siena’s hidden sides, quiet gardens, artisan workshops, and peaceful oratories.

Explore
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   $135.43   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.

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

Siena Wine Journey: Tuscan Tastings & Local Delights

5 (69)
2 hours
From   $73.74   per person
See details

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

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

Living Siena: Contrade, Craft & Sacred Spaces

5 (95)
3 hours
From   $98.32   per person
See details

Explore Siena's traditions through contrada pride, sacred rituals, and artisan craft, guided by your host and shaped by your interests.

FIVE-STAR REVIEWS

Google 4.9  ·  Tripadvisor 4.9  ·  Trustpilot 4.8

Hi, I’m Stella

Siena
5.0 (12)

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!

Visit Host Profile

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

Languages I speak

  • English
  • Spanish
  • Italian

Hi, I’m Letizia

Siena
4.8 (10)

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

Hi, I’m Silvia

Siena
5.0 (4)

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

See What Guests Are Saying

Find Reviews That Matter To You

Stella stepped in when the original guide backed out. She was a pure delight and knows Sienna and its history extremely well as a multi-generational citizen of Sienna. We were fortunate to meet her!

S
Susan 31 October 2026
Siena

Great!!

D
Debra 8 October 2026
Siena

Positive feedback from my clients who traveled as two couples.

L
Leonard 8 August 2026
Siena

Perfect tour. Exactly as we wanted. Highly recommend

S
Sabrina 27 October 2026
Siena

Our tour guide Lilo was terrific and Siena was beautiful . It was a great introduction.

C
Carrie 25 October 2026
Siena

Leticia was fun and enthusiastic. She was also thoughtful about the seniors in our group. It was clear that she loved Siena and her love for the city was infectious.

M
Maria Cecilia 8 October 2026
Siena

Lillo was fantastic!!! Entire tour was stress free, thorough, and flexible to whatever we wanted to see, with great picture spots and restaurant recommendations. We can’t wait to be back! Thank you Lillo!

T
Tiffany 7 October 2026
Siena

The tour was comprehensive and wide ranging. Filippo my guide was very knowledgeable and demonstrated as detailed understanding of Siena. I visited all the key sites of the city except the Castle. The tour was for three hours.

R
Robert 7 October 2026
Siena
See all reviews in Siena

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.