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

“A great tour of Siena. If you only have a short time in this beautiful city I would highly recommend this tour. We learned so much about the city from our guide, Giorgia, who was extremely knowledgeable and clearly passionate about her city. We loved…”

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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

“Lucky to be one of two on the tour. Wonderful history lesson and background to the contrade and Palio. Claudia was really nice and well informed, perhaps best early in 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

“Georgia was wonderful. Extremely knowledgeable. Tailored the tour to our group and set the perfect pace. Highly recommend this tour if the assigned guide is even half as good her.”

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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

“We all loved this tour round the beautiful Siena. My husband, myself and our three teenage sons. The guide was friendly and gave a really interesting overview of life in the city historically, showing us where you can spot those details today. The food and…”

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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

“The tour today was fantastic. Oleksandra was so engaging and knowledgeable. She answered ever question fully. The group of ladies I met were kind and fun. We started our tour with a great wine bar before continuing on to see the city and taste some…”

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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

“This was the perfect way to see the highlights in Siena. Sylvia was very knowledgeable and really helped us learn the history of this great place. She spent quality time with us and really went above and beyond our expectations.”

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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

“Lovely city very easy to walk around. Guide was not that knowledgable but tried her best seemed very set on getting done in the hour”

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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

“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

“Roberta gave us a wonderful combination of the secret walking tour and the best of Siena, since we were visiting for the first time. We have one in our party who has some difficulty walking and she was very mindful of that. We had a…”

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