Siena

15 Best Siena Walking Tours

The walks through the Palio’s city: the shell-shaped Campo, contrada flags decoded and medieval lanes that out-stubborned the Renaissance. Siena froze at its golden moment; the guides explain why that was the luckiest plague in history.

1.Siena: Walking Tour and Skip-the-Line Duomo Tickets

Discover Siena’s medieval charm on a 2-hour walking tour, including skip-the-line access to the stunning Duomo and insights from expert guides.

Most Popular★ 4.8

“Starting point was great. The guide was terrific, interesting, knowledgeable, and enthusiastic. Excellent all around. I would recommend this to anyone. You really got a feel for sienna, the history and the culture of sienna..”

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2.Skip the Line: Siena Duomo and City Walking Tour

Discover Siena's highlights on a 2-hour guided tour, including skip-the-line entry to the Duomo, with expert insights into this UNESCO city.

★ 5.0

“Lovely tour guide (Silvia). Very informative, kind and funny. Loved the tour itself - very well designed and just enough time to get information on the city, leaving time to explore afterwards and of course enjoy the amazing Tuscan food.”

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4.Discover the Medieval Charm of Siena on a Private Walking Tour

Explore Siena’s top sights on a private 2-3 hour walking tour with a knowledgeable guide. Discover historic landmarks, legends, and local traditions comfortably.

★ 5.0

“Barbara was a great guide. We saw the Siena highlights and got a great intro into the history of Siena, a great way to start your stay!”

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5.Private Tour: Secret Siena Walking Tour

Discover Siena’s hidden gems on a private 3-hour walking tour with expert guides, exploring lesser-known streets, churches, and panoramic views.

★ 5.0

“I cannot imagine a better tour guide than Elio. He took the time to shape the tour around our interests. It was far more than we hoped for. Elio gave us insight into the Basilica, the contrade, and even shared his expertise in Tuscan wines.…”

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6.Siena walking tour with lunch & Chianti wine

Discover Siena’s charm on a guided walking tour with authentic Tuscan food, regional wines, and hidden sights—perfect for lovers of history and cuisine.

★ 5.0

“Fun tour, good food and lots of history, it was a small group which made it special. Lots of walking but you don't notice how far you ha e gone and you stop at the perfect time for a snack!”

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8.Private Tour: Siena Walking Tour

Discover Siena's highlights with a private 2-hour walking tour led by a passionate guide, exploring iconic sights, hidden gems, and local stories.

★ 5.0

“Great tour of a beautiful City. Sylvia is an extremely knowledgable and entertaining guide and the time just went so fast. We especially loved the background On the Palio. Would highly recommend this to other travellers.”

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9.Guided Walking tour of Siena with Cathedral

Discover Siena’s medieval charm on a guided walking tour that covers top sights including Piazza del Campo, Siena Cathedral, and local history—perfect for a quick, authentic experience.

★ 3.5

“Helena was great and we learned a a lot about the history of Siena. She was patient and lots of fun. We thoroughly enjoyed the whole experience!!!”

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10.Siena Walking Tour with Audio and Written Guide by a local

Explore Siena’s highlights with a flexible self-guided tour, including key monuments, local tips, and authentic food suggestions for a memorable visit.

★ 4.0

“This was a good way to take in Siena. However, there needs to be warnings about the steep climbs and descents on the route, and possible alternative routes or suggestions where a taxi might hit be a good choice for less able-bodied folk. I made…”

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12.Siena Sightseeing Walking Tour with Food Tastings for Small Groups or Private

Discover Siena’s highlights and local flavors on this 2.5-hour guided walking tour, including food tastings, with options for small groups or private experience.

★ 5.0

“Anna was a fantastic tour guide with so much knowledge of Siena’s history and culture. She was so energetic and passionate during our tour, explaining so much and making it real and exciting for us. The good portion was very enjoyable. It was great for…”

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13.Siena Highlights Private Walking Tour With A Guide (Private Tour)

Discover Siena's highlights on a private 3-hour walking tour. Visit Piazza del Campo, Siena Cathedral, and more with expert guides for an authentic experience.

★ 5.0

“Our walking tour of Siena took an unexpected turn right at the very beginning, and we cannot thank our guide, Andrea, enough for her incredible kindness and support. Bad weather had already delayed us, and Andrea graciously adjusted her schedule. Then, one of our friends…”

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14.Secret Siena Walking Tour

Discover Siena’s hidden corners and medieval stories with a private guide. A 2-hour walking tour offering authentic sights, peaceful views, and local legends.

★ 5.0

“Roberta was amazing. I definitely felt like I discovered secret areas of Siena. And incredible photo ops too! Well worth the money soent”

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15.Siena Private walking tour

Discover Siena’s highlights on a private 2-hour walking tour with a local guide, exploring top sights like Piazza del Campo, the Duomo, and Santa Caterina.

★ 5.0

“Volevamo avere una guida tutta per noi e così è stato! Con entusiasmo, passione e generosità Roberta ci ha accompagnato nella visita al Duomo e poi tra le vie di Siena per un trekking urbano.”

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More Siena Walking Tours

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A striped Duomo, a shell-shaped square and Brunello next door.