Siena Private Walking Tour: Medieval Streets & Palio Stories

Walk Siena's medieval heart with a guide who knows the bankers, pilgrims and noble families behind it

A private walking tour of Siena led by a local English-speaking guide for two hours, covering the Basilica of San Domenico, Siena Cathedral, Piazza Il Campo and the city's historic banking district. The tour includes entry to elegant palace interiors, a tasting of ricciarelli traditional cookies, and stories of the Palio horse race and the families who shaped the city. Cathedral tickets are optional and purchased separately.

Step-by-step itinerary

Stops and time spent at each

1. Basilica of San Domenico10m · entry included
2. Siena Cathedral30m
3. Pubblico Palace15m · entry included

Explore Siena's historic landmarks

• Visit Basilica of San Domenico
• See barocco chapel in Saint Caterina house
• Discover Monte de Paschi 1472 Bank square
• Walk along elegant historical street
• Explore Siena Cathedral's artworks
• Visit Piazza Il Campo and Palio sites

The experience

You arrive in Siena with a free afternoon and no plan to navigate the medieval streets alone. A private guide meets you and walks you through the city's real layers: not just the famous landmarks, but the banking quarter where Monte de Paschi was founded in 1472, the elegant Banchi di Sopra street, and the interiors of palaces once owned by noble families. The tour is built around stories: the merchants, pilgrims and bankers who made Siena rich, and the traditions that still define it, like the Palio, the horse race that takes over Piazza Il Campo each year.

You'll stand in the Basilica of San Domenico to learn about Santa Caterina of Siena, visit a small baroque chapel in what was once her house, and walk through the cathedral itself to see the floor mosaics, Michelangelo's altar, Bernini's chapel and the Nicola Pisano pulpit. Piazza Il Campo, the main square where the Palio races happen, shows you the town hall and the Fonte Gaia fountain. The guide explains the districts, the contrade, that compete in the race and the centuries of tradition behind it. You finish with a small tasting of ricciarelli, the traditional almond cookies Siena is known for.

The tour runs two hours and stays on foot through the city center. Cathedral entry is optional. If you want to go inside, you buy tickets separately at the door. The guide can tailor the route to what interests you most, so if one stop matters more than another, say so at the start.

What’s included

• Walking tour with a local licensed English-speaking guide for two hours.
• entry to the Basilica of San Domenico, a baroque chapel in the former house of Santa Caterina, and the interiors of elegant historic palaces.
• a small tasting of traditional ricciarelli cookies.
• access to Piazza Il Campo and the historic banking quarter.

Options for this experience

3 options

Two-hour private Siena tourUp to 6 per booking · Guide in English · No fixed timeSpecial Siena tour lasting 2 hours: Enjoy a complete visit of Siena, including the Classic and Secret tour in 2 hours, with the Duomo or a Contrada (tickets not included)

Siena tour with the Duomo includedUp to 2 per booking · Guide in English · No fixed timeSiena tour with Duomo included: A special tour for couples, with Duomo tickets included. Discover the Duomo of Siena on a guided tour of Siena and the Duomo, to see the masterpieces of Michelangelo, Bernini and Donatello. Skip the line.

Small group Siena private tourUp to 15 per booking · Guide in English · No fixed time

You'll see the exact price of each option when you check availability.See dates and prices

Before you book

Days and timesEvery day

GroupPrivate

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends at a different place from where it starts.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

ConfirmationConfirmation within 48 h

Prices and times updated 10 days ago

Good to know

Low physical effortWheelchair accessibleStroller-friendlyPets welcomePublic transport nearbyInfants must sit on laps

Operated by Roberta Marioni

Is this one for you?Book the private option if you want the route and pace shaped to your interests. Choose the small group version if you'd rather share the cost with other travelers and don't mind a fixed itinerary.

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Top questions

What is the Palio and why does the tour spend time on it?

The Palio is the famous horse race held twice a year in Piazza Il Campo, where the city's districts, called contrade, compete. The tour visits the square and explains the districts and the centuries of tradition behind the race, so you understand what you're seeing when you walk through the city.

Do I need to buy tickets for the Cathedral and the Basilica?

The Basilica of San Domenico is included in the tour. The Cathedral is optional. If you want to enter and see the mosaics, Michelangelo's altar and the other artworks inside, you buy a ticket at the door when you arrive.

What exactly happens during the ricciarelli tasting?

You get a small tasting of ricciarelli, the traditional almond cookies that Siena is known for, as part of the tour. It's a brief stop to try the local specialty, not a full meal or extended food experience.

Can the tour be changed if I'm more interested in one part of Siena than another?

Yes, the tour can be customized and tailored to your interests, so if you want to spend more time on the banking history, the Palio, the palaces or any other part of the city, tell your guide at the start.

Is this tour walkable for someone who isn't very fit?

The tour is suitable for all physical fitness levels and takes place on foot through the city center. The route is wheelchair accessible, and if you're traveling with a small child, you can bring a pram or stroller.