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.

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

“So glad we did this tour. We were very fortunate that it was only myself and a friend so we had Georgia to ourselves! She was a fantastic guide and so knowledgeable about the history of Siena. Georgia made the tour very specilaised and answered…”

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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

“This is a great tour to take if you are only in Siena for a day or two or if 10 days - do it on the first day - it will make the remainder of your trip more enjoyable. Silvia was born near here…”

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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

“Our guide Ludivica was extremely personable, professional, and very informative. We thoroughly enjoyed our time with her.”

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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

“Excellent Walking Tour. Lasts about 3 hours. Giorgia was fabulous and a wealth of information. We learned a lot about the history of Siena, the layout of the town, the Palio, and the Duomo.”

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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

“Amazing. Loved it. Our guide, Julie, was very knowledgeable about Siena, the rich history and the food. Can highly recommend this tour.”

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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

“This was our first activity after checking in to our hotel. Wine, snacks, gelato, and treats—with three stops to indulge. And a bit of local culture too. What could be better?”

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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

“Sylvia is easy to understand and made it very unique - we learned a lot about the Palio since it had just happened”

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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

“Our guide Anna was well prepared and of great culture. She was able to let us enjoy every moment of our tour. We suggest this tour to all tourists. Thank you!”

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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

“Anja was an amazing guide who showed us around Siena as if we were friends coming to visit. She was very knowledgeable in various subjects and tailored the experience for our personal tastes. Would definitely recommend to everyone!”

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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

“We had a great tour of Siena with our guide Marianna. She took us around to all the great historical areas and some secret spots. We walked over 10,000 steps in 3 hours. It was December 1st, the beginning of the new year! We also…”

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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

“This tour did not provide the depth of knowledge we have received from other private tours in the past. This also felt like a normal walking tour, not a “Secret Siena” tour. For example we walked past the Basilica of San Domenico as part of…”

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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

“solo una parola: FAVOLOSA! Ho contattato Roberta per creare un momento speciale e diverso dal solito in occasione dell’addio al nubilato di una cara amica. È stata super! Passeggiata per Siena tramite il racconto delle storie colorate di donne Senesi, aneddoti divertenti su come si…”

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More Siena Walking Tours

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