Walking Tours

TUSCANY

10 Best Walking Tours In Siena

Most booked first.

Our shortlist of the 10 most-booked walking tours around Siena, ranked by what travellers actually rated. Who runs them, how long they take, what they cost.

10 Best Walking Tours In Siena

Skip the Line: Siena Duomo and City Walking Tour

Skip the Line: Siena Duomo and City Walking Tour - Basilica Cateriniana di S. Domenico: red brick Gothic and Catherine relics

Siena: 3h Private City Walking Tour with Optional Cathedral

Siena: 3h Private City Walking Tour with Optional Cathedral - Piazza del Campo to Palazzo Pubblico: Siena’s political heartbeat on foot

Siena Walking Tour with Cathedral and Crypt & Museum Option

Siena Walking Tour with Cathedral and Crypt & Museum Option - Contradas, Old Ghetto corners, and the Palio story that actually clicks

4.Siena Walking Tour with Cathedral and Crypt & Museum Option

4.9

Walk Siena’s medieval streets with skip-the-line Duomo entry. Add OPA SI Pass for crypt, museum and panorama. Small group, 2-3 hours.

“Our guide and tour was outstanding. We have taken many walking tours both large and small over the last 15 years and this tours ranks as one of the best. Flo is a great knowledgeable guide.”

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Discover the Medieval Charm of Siena on a Private Walking Tour

Discover the Medieval Charm of Siena on a Private Walking Tour - Santa Caterina sanctuary area: seeing the house without a full detour

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

5.0

Private 2–3 hour walking tour of medieval Siena with a licensed guide: Palio stories, St Catherine relics, and Duomo secrets.

“We had a lovely day with Barbara! Learned so much but not too much. Pleasant and highly knowledgeable. There is a lot to Sienna and we would have missed so much. Highly recommend!”

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Private Tour: Secret Siena Walking Tour

Private Tour: Secret Siena Walking Tour - A private, customizable route that fits your energy (and your schedule)

7.Private Tour: Secret Siena Walking Tour

5.0

Private Secret Siena walking tour from Piazza del Campo with a guide, free church stops, contrade Palio stories, and flexible timing.

“Wow, just awesome. Georgia was outstanding. We even booked her for another tour later in the week. This was the most enjoyable part of the vacation…we learned so much…i highly recommend this tour!”

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Siena walking tour with lunch & Chianti wine

Siena walking tour with lunch & Chianti wine - Meeting at Hotel NH Siena and how the route flows

8.Siena walking tour with lunch & Chianti wine

5.0

A 2.5-hour Siena walk with organic gelato, underground wine stories, sparkling tastings, and lunch with Chianti for small-group value.

“Our tour guide Mohad was incredibly knowledgeable, not only about Siena’s history but also about all the food, wine and gelato places. Some of them truly hidden gems!”

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Siena Private Walking Tour: Traditions, Streets & Cathedral

Siena Private Walking Tour: Traditions, Streets & Cathedral - Piazza San Domenico: the quick first look that helps everything click

9.Siena Private Walking Tour: Traditions, Streets & Cathedral

4.5

Private Siena walking tour with skip-the-line Duomo entry, contrade and Palio stories, plus optional crypt and museum.

“Susanne was excellent! Gave the right amount of information on the history, culture, traditions and of course food in the region. A gentle pace walking around some of the amazing streets in this living museum city. The Duomo certainly stands out Definitely enriched our stay.”

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