Introduction: A Walk Through Siena’s Timeless Streets
A private walking tour of Siena offers a fantastic way to get your bearings in this beautifully preserved medieval city. While Siena’s compact center is easy to explore on your own, having a knowledgeable guide like Roberta Marioni enriches the experience with storytelling and local insights you won’t find in a travel guide. For around $240 per group—up to six people—you get approximately two hours of focused sightseeing, covering everything from historic churches to the lively Piazza del Campo.
What I particularly like about this tour is how flexible it is. You can schedule it either in the morning or the afternoon, fitting it neatly into any itinerary. Plus, the stops are thoughtfully curated: from the church of Saint Catherine to Michelangelo’s works in the Duomo, each site offers a glimpse into Siena’s past and its artistic treasures. And, since the tour is private, your group can set the pace and focus on what interests you most—making it a truly tailored experience.
One thing to keep in mind is that tickets to the Duomo and certain museums are not included, so if you want to see the incredible floor mosaics or Michelangelo’s altar, plan to buy those tickets separately. Still, with knowledgeable commentary from Roberta—who receives glowing reviews—you’ll leave feeling like you’ve unlocked Siena’s secrets with a trusted local.
Key Points / Takeaways
Personalized Experience: The private nature means you get a guide who can tailor the pace and focus on your interests.
Rich Itinerary: From Santa Caterina to Piazza del Campo, each stop has meaningful historical and artistic stories.
Flexible Scheduling: Choose morning or afternoon to best align with your plans.
Local Guide Expertise: Roberta’s enthusiasm and knowledge bring Siena’s story to life—highlighted in reviews praising her passion.
Cost-Effective for Groups: At under $250 for up to six people, it offers good value for a personalized, educational experience.
Skip the Lines? While tickets to specific sites are not included, the guide’s insights help you appreciate each stop even if you don’t go inside.
Exploring Siena’s Top Sights: A Detailed Breakdown

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Starting Point: Basilica Cateriniana Di S. Domenico
Your tour begins at the Basilica of Saint Domenico, a striking church with a history intertwined with Siena’s beloved Saint Catherine. Here, your guide shares the story of her life and the significance of her head, giving you a personal connection to Siena’s spiritual heritage. The church’s architecture and artworks make it a worthwhile first stop, and the inclusion of the admission ticket simplifies your visit. Expect about 10 minutes here, but Roberta’s commentary means you’ll leave knowing much more than just what you see.
Santa Caterina’s Sanctuary and Monastery
Next, you’ll visit the Santuario di Santa Caterina, a baroque chapel and a decorated hall that was once her home. This small monastery offers a glimpse into the saint’s life and the local veneration she still receives. The quiet atmosphere combined with Roberta’s stories makes this a memorable stop, especially if you’re interested in religious art and history. Again, admission tickets are included, making this a seamless addition to your walk.
The Historic Bank: Banca Monte dei Paschi di Siena
A visit to Siena isn’t complete without a nod to its banking past—the Monte dei Paschi di Siena, founded in 1472, is one of the oldest continually operating banks in the world. The square outside the bank’s historic building is a visual treat with its classical architecture. While the tour doesn’t include inside access, learning about Siena’s long banking tradition adds a layer of understanding to the city’s prosperity and history.
The Duomo di Siena: Art, Architecture, and Michelangelo
The highlight for many is the famous Siena Cathedral, a masterpiece of medieval architecture. While the tour doesn’t include tickets, your guide will point out highlights such as the intricate floor mosaics, Bernini’s chapel, Donatello’s statues, and Michelangelo’s altar. Expect about 30 minutes here, during which you’ll get a detailed verbal tour of the interior’s art and symbolism. If you wish to go inside, plan ahead to buy tickets separately, but the guide’s commentary will help you understand what you’re seeing.
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Piazza del Campo: The Heart of Siena
The tour concludes at Siena’s iconic main square, Piazza del Campo. Known worldwide for the Palio horse race, this square is the social hub of Siena. Roberta explains the history behind its unique shell shape, its elegant medieval palaces, and the imposing Town Hall. You’ll also see the Fonte Gaia, a beautifully decorated fountain that’s a favorite photo spot. Spending about 15 minutes here, you’ll leave with a sense of Siena’s lively civic spirit.
Price and Logistics: Is It Worth It?
At $242.93, this private tour offers good value considering it covers a lot of ground with a licensed local guide and is tailored to your group. The cost is per group, not per person, making it an economical option for families or small groups wanting a personalized experience. The two-hour duration keeps it manageable within a busy sightseeing day, and the flexibility of scheduling allows you to fit it into your plans.
One point to consider is that museum and cathedral tickets are not included, so if you’re eager to see the interiors, you’ll need to budget extra time and money. However, many reviews highlight how Roberta’s storytelling compensates for not going inside—she vividly describes the artworks and architecture, enriching your understanding even from the outside.
Who Will Love This Tour?

This experience is ideal for travelers who want an overview of Siena’s main sights with the guidance of a passionate local. It’s perfect if you prefer a private, flexible schedule over group tours, especially if you’re traveling with a small family or a group of friends. History enthusiasts will appreciate the storytelling, while art lovers benefit from insights into the cathedral’s masterpieces. If you’re short on time but want a meaningful introduction to Siena, this tour hits the mark.
The Sum Up: Who Should Consider This Siena Private Walking Tour?

For anyone eager to explore Siena’s historical streets with a knowledgeable guide, this tour offers a well-rounded introduction. It’s especially suited for those who value personalized attention and want to avoid the crowds, as you’ll have the guide’s undivided focus. The stops are thoughtfully selected, giving you a taste of Siena’s religious, artistic, and civic history in just a couple of hours.
While the price might seem steep for a two-hour walk, the inclusion of a private guide, the flexibility, and the depth of storytelling make it worth the investment. It’s a practical way to gain a meaningful understanding of Siena’s highlights, especially if you’re keen on authentic experiences rather than just snapping photos.
If you hesitate about navigating Siena’s labyrinthine streets or want to ensure you don’t miss key sites, this tour simplifies the process and enhances your visit. Whether you’re on a short trip or simply want a curated introduction, this private tour is a valuable addition to your Siena itinerary.
FAQ

What is included in the tour?
You’ll get a private walking tour with a licensed local guide, covering several key sites in Siena including Saint Domenico, Santa Caterina, the Duomo, and Piazza del Campo. Admission tickets for certain sites are included, but tickets for museums and the Duomo are not.
How long does the tour last?
Approximately two hours, which is enough time to see the highlights and hear stories without feeling rushed.
Can I customize the itinerary?
Yes, since it’s a private tour, you can discuss your interests and pace with Roberta, making it adaptable to your preferences.
What should I bring?
Comfortable walking shoes, a water bottle, and perhaps a camera. If you want to visit inside the Duomo or other sites, plan to buy tickets separately.
Is it suitable for families or groups?
Absolutely. It’s designed for small groups of up to six people, making it perfect for families or friends traveling together.
How do I book this tour?
You can book in advance, often 26 days ahead on average, through Viator or directly with Roberta Marioni’s contact info provided.
In essence, this Siena private walking tour offers a personalized, engaging, and practical way to discover the city’s most cherished sights. Ideal for those who want expert insights without the hassle of self-guided navigation, it guarantees a memorable introduction to Siena’s timeless charm.
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