Walking Tours

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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

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

Siena: Walking Tour and Skip-the-Line Duomo Tickets - Basilica di San Domenico: more than a stop on the map

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

Most Popular 4.8

2-hour Siena walking tour with skip-the-line Duomo access, San Domenico stories, Contrade and Palio context, plus major Renaissance art.

“it is so amazing to do a tour with someone who LOVES his city, and I now love his city, the stories, the history, such a wonderful place to visit....highly recommend this tour.”

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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

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

5.0

A 2-hour Siena walk with skip-the-line Duomo entry, contrade stories, major piazzas, and art inside the cathedral for about $48.

“Really enjoyable. The duration for walking tour was just right, our guide was knowledgeable, humorous and gave interesting commentary about Siena”s history and culture.”

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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

3.Siena: 3h Private City Walking Tour with Optional Cathedral

4.7

Private 3-hour walk through medieval Siena from San Domenico to Piazza del Duomo, with Palio/Contrade stories and optional cathedral access.

“Brava Ludmila, bel giro per le strade di Siena, con aneddoti e informazioni utili per comprendere meglio la storia della città e le tradizioni del luogo.”

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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.

“Mare, our guide was exceptional. She spoke passionately about Siena and took the time to explain the importance of each of the places we visited on this walking tour. A great way to learn about the history of Siena!”

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Discover Siena: Guided Walking Tour and Cathedral Visit

Discover Siena: Guided Walking Tour and Cathedral Visit - Piazza del Campo and Palazzo Comunale: Siena’s Political Heart

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.

“Our guide, Dace, was incredibly knowledgeable about her city. She tailored the itinerary to our interests based on our questions, comments, and reactions, and she made our experience in Siena so much better than it would have been without her guidance. She even took us off the typical route to see her cantrada’s fountain &…”

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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.

“Elio was fantastic! He customized our tour as he learned about our interest. It was the perfect way to learn about the city. Thank you!”

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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.

“Great local recommendations, very interesting information about the city, and delicious food and drinks. Morad is a great host, very friendly and knowledgeable.”

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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.

“The meeting place and tour guide were easy to spot, unlike some of the other tours we had booked. She was very friendly and knowledgeable and made the tour very enjoyable. It was a small group and we were able to ask a lot of questions and had time to take photos along the way.…”

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Walking Tour in Siena with Tastings and Stories

Walking Tour in Siena with Tastings and Stories - Meeting at Palazzo Salimbeni/Spannocchi, then getting oriented fast

10.Walking Tour in Siena with Tastings and Stories

4.8

Walk Siena with a local, tasting local wines, ricciarelli, and Il Bacio gelato, plus contrade and Palio stories in 2.5 hours.

“Jacopo our guide was fabulous - very knowledgeable about the city's history, full of interesting facts and great company (with perfect English). We learnt and saw things about the city we would have missed without him.”

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