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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3.Siena: Guided Walking Tour with Cathedral Entry

Discover Siena's highlights on a 90-minute guided walking tour, including entrance to the cathedral — perfect for history lovers and first-time visitors.

★ 4.3

“Coming to Siena just for a day, this 2-hour tour was perfect: it gave us enough important information in the very beginning of the day, after which we could explore the city and its treasures on our own. Highly recommend for first-time one-day travelers.”

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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

“My tour guide Sylvia was excellent. Highly recommend this tour. She is a wealth of knowledge on Siena. And what a wonderful person she is !! Seeing the back streets and hearing the history was fantastic.”

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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

“Julie was a wonderful guide, however I feel like there were some areas where she shared too much details that made me lose attention. Also, I felt like the description was a bit misleading, I thought this was a tour with multiple tastings and lunch…”

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7.Walking Tour in Siena with Tastings and Stories

Discover Siena’s hidden gems on a 2.5-hour walking tour with local guides, tasty tastings, and stories that reveal the city’s authentic charm.

★ 4.8

“Jacopo was a great guide and gave such meaning to our trip in Siena due to all the amazing information he gave us, we were able to see Siena in a different light. He has great enthusiasm, was really friendly and had patience for my…”

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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

“The tour was great. Silvia was helpful, showed us around, answered all of our questions and was, in general, an awesome tour guide. I’m not a fan of Viator but feel very lucky that Silvia was our guide.”

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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

“The history of the city and the families who compete in the Palio. The tour of the Cathedral was wonderful - what an amazing space!”

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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

“We did not have time for a guided tour so this was a nice way to learn a little about the main sites. We did crave a bit more history about Sienna though!”

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11.Siena: Food and Wine Walking Tour

Discover Siena’s culinary delights on a 2-hour food and wine tour. Taste local wines, cheeses, and more with a friendly guide in the charming streets of Siena.

★ 4.9

“Tour and learning about all the regional wines along with tasting them was amazing! Our guide was local and charming.”

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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

“We expected a small group, but it turned out that it became a private tour when the other people were not able to get there on time. Our guide was very knowledgeable about Siena and the foods. We enjoyed learning a lot, even though we'd…”

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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

“Great walking tour of Siena. Our tour guide, Andrea, was excellent. She was very patient with my 92 year old Dad and she did her best to get us a cab.”

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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

“Our tour guide skillfully lead us to the sights but took us in a way that we were never in crowds. She taught us so much!”

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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

“The visit to the city of Siena led by Mrs. Roberta allowed us to appreciate aspects of its history that we would otherwise have ignored. A city is not only art and architecture, however admirable, but also the history of those who brought it to…”

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