If you’re considering a private guided tour of Siena, Italy, this experience offers a thoughtful glimpse into the city’s most iconic sights and lesser-known treasures. While I haven’t personally taken this tour, the detailed itinerary and glowing reviews suggest it’s a well-rounded introduction to Siena—ideal for those wanting an engaging, personal touch without the crowds.
What we love about this tour is how it balances famous landmarks like the Duomo and Piazza del Campo with quieter, more intimate spots such as Santa Caterina’s church and the historic Banca Monte dei Paschi. The guide, Roberta, seems to be a highlight here—her knowledge and anecdotes bring Siena’s stories alive, according to travelers. One thing to consider is that ticket prices aren’t included, so you should budget extra for entrance fees if you want to go inside some of the sites. This tour is especially suited for travelers who want a comprehensive yet flexible Siena experience—perfect for history buffs, art lovers, or anyone looking to deepen their understanding of this captivating city.
Key Points

- Personalized experience with a private guide ensures tailored storytelling and flexibility.
- Famous sites like Siena’s Duomo and Piazza del Campo are thoughtfully incorporated, along with lesser-known corners.
- Knowledgeable guide Roberta consistently earns praise for her storytelling, anecdotes, and friendliness.
- Price point of around $242 for up to 6 people offers good value for a private tour, especially considering the depth of insight.
- Site tickets are not included, so travelers should plan for extra costs.
- Duration of about 2 hours makes this a manageable, enriching overview without feeling rushed.
This tour promises a comprehensive walk through Siena, mixing major sights with local stories. It’s a chance to see the city through the eyes of someone who knows its hidden corners and history intimately. Whether you’re a first-time visitor or someone returning to Siena, this tour offers both familiar highlights and fresh perspectives.
Starting Point: Piazza San Domenico
The tour kicks off at Piazza San Domenico, a central spot in Siena that sets the tone for your exploration. From here, the guide begins weaving stories as you walk toward the city’s most celebrated landmarks. The private nature of the tour means you can tailor your experience or linger at points that catch your interest.
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The Siena Duomo: A Masterpiece

The first stop is the Duomo di Siena, arguably the city’s crown jewel. This cathedral is a stunning example of Gothic architecture, with a rich history that’s fascinating to explore. When you visit, you’ll see the inlaid floor, a true highlight, visible in summer when the church is open. The floor consists of 56 squares created between 1300 and 1500—each telling its own story.
Inside, we loved the Piccolomini Library, decorated with frescoes by Pinturicchio based on drawings by Raphael, which makes for a truly special viewing experience. Other notable features are Michelangelo’s Piccolomini altar, Bernini’s chapel of the vow, and Nicola Pisano’s pulpit—each piece a testament to Siena’s artistic heritage. Keep in mind, admission tickets aren’t included, so plan to purchase those ahead or on-site if you want to step inside.
Travelers consistently praise the guide’s storytelling here. One reviewer mentioned how Roberta’s anecdotes made the visit memorable, saying she “enriched the tour” with her detailed knowledge. For art lovers, this stop alone is worth the price of the tour.
The Historic Monte dei Paschi Bank
Next, the guide takes you to the Banca Monte dei Paschi di Siena, the world’s oldest bank still in operation. The architecture of the Salimbeni Palace is impressive, and the story of Siena’s medieval banking tradition adds an intriguing layer to your understanding of the city’s history. It’s a quick stop, about 10 minutes, but packed with storytelling potential.
Palazzo Chigi Saracini and Santa Caterina’s Sanctuary

The tour then moves to Palazzo Chigi Saracini, a noble residence that became a renowned music academy. Its history and artistic significance offer a glimpse into Siena’s aristocratic past. Just a short 10-minute visit, but notable for music and cultural buffs.
Following that, you visit the Chiesa del Santuario di Santa Caterina, where you can feel the spiritual atmosphere and learn about Catherine of Siena, one of Italy’s most revered saints. The church and her house, now a Dominican monastery, are beautifully preserved. The guide’s insights into Catherine’s mysticism make this a meaningful stop. The church and oratory are included in the tour, and the ticket here is covered, which is a bonus.
Piazza del Campo: The Heart of Siena

No visit to Siena is complete without a stop at the Piazza del Campo. This iconic shell-shaped square is where Siena’s centuries-old Palio horse race takes place, an event steeped in tradition and pageantry. The tour offers a lively account of its history and significance, making it more than just a scenic spot.
You’ll get about 20 minutes here to absorb the atmosphere, snap photos, and hear stories of Siena’s political and social history. Many reviews emphasize how the guide’s storytelling made the square come alive, connecting past and present.
Appreciate having local insight? Here are other guided experiences in Siena we've examined
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Via Banchi di Sopra and the Medieval Streets

Walking along Via Banchi di Sopra, the ancient road connecting Siena to the pilgrimage route of Francigena, adds a sense of continuity and history. The street’s noble palaces and towers are reminders of Siena’s medieval grandeur. It’s a quick, 10-minute stroll, but one that enriches your understanding of how Siena was a hub of commerce and culture.
Santa Maria della Scala: Medieval Hospital

The final stop is the Complesso Museale Santa Maria della Scala, once an ancient hospital serving pilgrims and travelers. Though the tour stops outside this complex, travelers can choose to visit inside for an additional fee. The building itself is historic, and its stories add depth to Siena’s role as a city of care and hospitality during medieval times.
Siena private guided tour for families
“Our family of 5 had an awesome time visiting Siena thanks to Roberta. She is very knowledgeable and has a lot of anecdotes to enrich the tour. We h…”
The Practicalities: Price, Duration, and Booking

Priced at $242.85 for up to 6 people, this private tour offers good value—especially if you’re traveling with family or a small group who appreciates personalized attention. The duration of approximately 2 hours makes it a manageable, engaging way to see Siena without feeling exhausted or rushed.
It’s worth noting that ticket costs are not included, so you should plan for extra expenses at sites like the Duomo and Santa Caterina’s church. The tour is available with a mobile ticket, adding convenience to your planning.
Based on the reviews, Roberta’s guided approach seems to elevate the experience, with visitors praising her knowledge, anecdotes, and friendliness. One reviewer even mentioned she took the group to the best bakery in town for a quick morning tea, which adds a friendly, local touch.
This tour suits history enthusiasts, art lovers, and those wanting a flexible yet rundown of Siena. Since it’s private, you can ask questions and move at your own pace—ideal for travelers with specific interests or families who want a more relaxed experience.
If you’re looking for a personalized tour with a knowledgeable guide that covers Siena’s main sights and some hidden gems, this is a solid pick. It’s especially good for those who want to avoid large crowds and prefer a more intimate, storytelling-focused experience. The focus on Siena’s art, architecture, and stories makes it suitable for travelers keen on cultural enrichment.
However, keep in mind that entrance fees are extra, so budget accordingly. This tour is best for travelers who want to maximize their time in Siena without the hassle of planning each site individually.
Are tickets to the Duomo and other sites included?
No, the tour does not include entrance tickets, so you’ll need to purchase those separately if you want to go inside the landmarks.
How long is the tour?
The guided experience lasts approximately 2 hours, perfect for a quick yet rundown of Siena.
Can I customize the itinerary?
Since it’s a private tour, you can likely ask the guide to focus more on certain sites or stories, making it adaptable to your interests.
Is this tour suitable for families?
While the reviews focus on general travelers, the duration and private nature could make it suitable for families, especially those with older children interested in history and art.
What’s the price for the whole experience?
It costs about $242.85 per group (up to 6 people), making it a cost-effective option for small groups or families.
Where does the tour start and end?
It begins at Piazza San Domenico and ends at Piazza del Campo, both central and easy to reach.
Is this tour available in multiple languages?
While the reviews mention the guide’s fluency in English, it’s best to confirm directly with the provider for other language options.
All in all, this Siena private guided tour offers a well-balanced experience that covers the city’s major sights with added personal stories and insider insights. It’s particularly suited for travelers who value knowledgeable guides, flexible pacing, and a deeper connection to Siena’s culture.
If you’re a history or art lover looking for a comfortable, engaging introduction to Siena, this tour ticks many boxes. Just remember to budget for entrance tickets, and you’ll be set for a memorable exploration of this medieval marvel.
Whether you’re visiting Siena for a day or just want a meaningful way to see the highlights, this private tour could be the perfect fit—especially with Roberta’s enthusiastic and informed guidance leading the way.
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