Review of the Siena Private Guided Tour for Families
If you’re planning a visit to Siena and want a way to enjoy this medieval city without the stress of navigating alone, a private guided tour might be just what you need. Based on detailed descriptions and glowing reviews, this tour offers a well-rounded introduction to Siena’s most famous landmarks and lesser-known treasures, all within about two hours. It’s designed for small groups—up to six people—and led by a guide who combines knowledge, storytelling, and a friendly attitude.
What I love about this experience is how it balances the highlights with unique stories that bring Siena to life. For instance, the guide takes you through alleys and medieval streets, revealing secret corners most travelers miss, and shares anecdotes about Palio, the centuries-old horse race that sparks local pride. Another big plus is the focus on famous artworks and historic buildings, like the Duomo and the Palazzo Chigi Saracini, which makes the tour both visually stimulating and educational.
The one potential drawback is that entrance tickets to sites like the Siena Cathedral or Santa Maria della Scala aren’t included in the price. That means you’ll need to budget extra for some of the stops, but many travelers find the guided commentary and tailored experience more than worth it. Plus, the tour’s flexible timing and private format make it perfect for families or small groups seeking a personalized exploration of Siena.
This tour offers a compelling mix of history, art, local legends, and authentic Siena experiences. If you’re looking for a way to see the city through an expert’s eyes while enjoying the comfort of a private group, it’s hard to beat.
Key points / Takeaways

- Customizable and intimate: Small group size (up to 6) means personalized attention and flexibility.
- Expert guide Roberta: Known for her knowledge, anecdotes, and friendly approach, her recommendations even extend to local food spots.
- Cultural highlights: Focus on Siena’s famous monuments, such as the Duomo, and stories behind Palio and Contrade.
- Rich details: Tour includes a deep dive into medieval architecture, noble palaces, and ancient sources.
- Authentic stories: Guides share lesser-known facts and stories that make the city come alive beyond the typical tourist spots.
- Extra site visits: Stops like the Monte dei Paschi di Siena bank and Santa Caterina’s house provide insights into Siena’s economic and spiritual history.
Exploring Siena: A Closer Look at the Private Guided Experience

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Introduction to Siena’s Historic Heart
This tour begins in Piazza San Domenico, a logical starting point that situates you right in the city’s core. Within a roughly two-hour window, your guide, Roberta, will lead you through Siena’s most significant sights, weaving history and legends into a seamless narrative. The tour is designed to be both engaging and manageable, especially for families or those with limited time but a desire for a comprehensive experience.
The Duomo di Siena: A Masterpiece of Art and Architecture
The Duomo di Siena is undoubtedly the star of the tour. Known for its striking façade and intricate marble details, this cathedral encapsulates Siena’s artistic grandeur. You’ll get a brief but enriching overview of its history, with a highlight on the summer inlaid floor—a stunning mosaic of 56 squares made from 1300 to 1500, which many travelers only see during specific seasons. The Piccolomini Library, adorned with frescoes by Pinturicchio and drawings by Raphael, is a standout feature. Visitors often mention the Michelangelo altar and Bernini’s chapel of the vow as highlights of the interior.
While entrance tickets are not included, many visitors say the guided commentary makes the visit worthwhile. Roberta’s stories give context to these masterpieces, making the experience more than just a walk through a church.
Monte dei Paschi di Siena: The World’s Oldest Bank
Next, the tour visits the historic Palazzo Salimbeni, home to Monte dei Paschi di Siena—the oldest bank in continuous operation worldwide. This stop offers insights into Siena’s medieval banking traditions, a fascinating glimpse into how the city prospered through commerce and finance. Though tickets are extra, the guide’s storytelling about Siena’s economic history adds depth to this small but meaningful stop.
Palazzo Chigi Saracini: An Artistic and Musical Treasure
The guide then takes you to Palazzo Chigi Saracini, a noble residence turned music academy. Here, you learn about Siena’s noble families and their cultural influence, especially their patronage of the arts and music. It’s a vivid example of how Siena’s aristocratic past continues to shape its identity today.
Loving the local insights? Here are more guided experiences we recommend in Siena
- Ride and Cook Like a Tuscan Is an Amazing Guided Bike Tour
- Siena: Guided Tour of Siena INCLUDING the Cathedral or Museum
- Lapi&Tour Guided Tour of the Cellars With Wine Tasting
- Private Guided Tour of Siena With a Licensed Local Tour Guide
- Siena Guided Tour With Cathedral and Optional Crypt & Museum
- Have You Ever Taken a Guided Tour of Siena?
The Mystic Santa Caterina and Her Legacy
A visit to Santa Caterina’s house, now a Dominican monastery, immerses you in the spiritual life of one of Siena’s most revered saints. The church and the oratory of the kitchen are beautiful, and the guide shares stories of Catherine of Siena’s influence on both the city and the Catholic Church—adding a personal dimension to the spiritual fabric of Siena.
Piazza del Campo: The Heartbeat of Siena
No visit to Siena is complete without stopping at Piazza del Campo, often called “the soul of Siena.” This shell-shaped square has hosted markets, festivals, and the renowned Palio di Siena horse race for centuries. The guide explains the square’s history, its stunning medieval palaces, and the tradition of the Palio, which continues to stir local passions. Visitors say the stories of the Contrade and the race itself are captivating, making the square more than just a pretty photo opportunity.
Via Banchi di Sopra: The Medieval Commercial Route
Walking along Via Banchi di Sopra, the ancient street once part of Via Francigena—the pilgrimage route to Rome—you’re immersed in the city’s medieval commercial life. The guide points out noble palaces and towers, sharing stories of Siena’s civic pride and architecture’s evolution. This street offers a glimpse into the city’s bustling past and its continued importance as a trading hub.
Santa Maria della Scala: A Medieval Hospital and Cultural Hub
Finally, the Complesso Museale Santa Maria della Scala stands as a testament to Siena’s long-standing tradition of hospitality and care. Built as an ancient hospital for pilgrims and travelers, it now functions as a museum complex. Although the tour only visits externally, many visitors are eager to explore its treasures, and the guide’s insights help frame its historical importance. For those interested, additional admission tickets can unlock further stories and artworks inside.
Practical Considerations and Value

While the tour’s base price of approximately $243 for up to six people might seem high at first glance, the value lies in having an expert guide tailor the experience to your interests, providing stories and context that bring Siena’s monuments alive. The private nature allows for flexible pacing and personalized attention—something hard to find in larger group tours.
Since admission tickets to some sites are not included, it’s worth budgeting extra for specific attractions like the Duomo or Santa Maria della Scala if you wish to delve deeper. Still, many travelers find that the guided commentary and insider tips compensate for the additional cost.
The tour duration of about two hours makes it manageable even for families with young children or those with tight schedules. Starting from Piazza San Domenico and ending at Piazza del Campo, the route covers key highlights while allowing for spontaneous exploration afterward.
Who Is This Tour Best For?
This experience is ideal for families, small groups, or first-time visitors looking for a curated overview of Siena. It appeals to those who value expert storytelling over just walking around on their own, and for travelers interested in history, art, and local traditions. If you enjoy personalized tours that balance famous sights with lesser-known stories, this is a good pick.
Final Thoughts
Choosing a private guided tour like this one offers a convenient and enriching way to see Siena. The knowledgeable guide, Roberta, earns praise for her ability to connect history with stories that resonate, making each stop memorable. The tour’s emphasis on authentic sites, coupled with stories about Siena’s contrade, palio, and noble past, ensures you leave with a deeper understanding of what makes this city so special.
The fact that many reviewers highlighted Roberta’s friendliness, expertise, and her tip to visit the best bakery in town shows how this tour offers a genuine local experience. While you’ll need to pay for some entrance fees, the overall value and tailored approach make it a worthwhile investment for your Siena visit.
Whether you’re a history lover, a family seeking a fun educational activity, or someone wanting a more personal perspective on Siena’s treasures, this tour has plenty to offer.
Frequently Asked Questions

Are entrance tickets included in the tour price?
No, tickets to sites like Siena’s Duomo, Santa Caterina’s house, and Santa Maria della Scala are not included and need to be purchased separately if you wish to visit inside.
How long is the tour?
The tour lasts approximately 2 hours, making it a manageable option for families or those with limited time.
Is the tour suitable for children?
Yes, the private format and engaging storytelling make it suitable for families, especially those interested in history and culture.
What is the meeting point?
The tour starts at Piazza San Domenico and ends at Piazza del Campo in Siena.
Can I cancel the tour?
Yes, there’s free cancellation available up to 24 hours before the scheduled start.
Who leads the tour?
The tour is led by Roberta Marioni, known for her knowledge, friendliness, and ability to adapt the experience to her guests.
Is tips included?
No, tips are not included; gratuities are at your discretion.
What language is the tour conducted in?
The guide speaks fluent English, ensuring clear and engaging communication.
In short, this private Siena tour offers a well-rounded, personalized way to discover Siena’s rich tapestry of sights, stories, and traditions. Perfect for small groups who want a flexible and deeply informative experience, it’s a recommended choice for making your Siena visit both memorable and meaningful.
More Guided Tours in Siena
- Siena: Guided Walking Tour with Cathedral Entry
- Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
- Tuscany: Self-Guided Video Tour with World’s Top Experts
- Siena: Guided Tour of the City and Cathedral in Italian
- Siena: Guided visit of the city in German
- Siena: Half-day Guided Hike to Monteriggioni
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