Siena walking tour with lunch & Chianti wine tasting

Medieval squares, secret alleys, and a lunch that tastes like Siena

A 2.5-hour walking tour of Siena led by a licensed English-speaking guide, moving through medieval neighborhoods, historic piazzas and hidden streets to taste gelato, wine and a full lunch of homemade pici pasta, pecorino cheese and Chianti. The tour keeps to small groups of no more than 12 people and includes an awarded gelato shop, wine tasting near Piazza del Campo, and a meal at a traditional osteria.

Step-by-step itinerary

Siena walking tour with food and wine

• Try gelato near Basilica of San Domenico
• View the oldest bank in the world
• Explore historical cafés and medieval alleys
• Taste local and regional sparkling wines
• Enjoy lunch with local delicacies and Chianti wine

The experience

What's the fastest way to eat and drink your way through Siena's real neighborhoods without spending the afternoon planning it? The tour starts near the Basilica of San Domenico with three organic gelato flavors at an award-winning shop, then moves to Piazza Salimbeni to see the Palazzo Pubblico: the oldest bank in the world, still operating since 1472. From there, the walk winds through medieval alleys and historical cafés near Piazza Indipendenza, where the guide shares local stories and traditions tied to the streets and buildings around you.

The wine tasting happens near Piazza del Campo with local and regional sparkling wines like Prosecco, and it's structured as an educational stop rather than a quick pour. Lunch follows at a typical osteria where you sit down to homemade pici pasta, pecorino cheese, cold cuts, bruschetta with extra virgin olive oil, and ricciarelli biscuits, paired with Chianti or white wine depending on what you choose. The menu shifts with the season, so what you eat depends on when you go. Vegetarian options are available throughout.

The tour runs rain or shine and works for families with children from age 3 onward. Infants can come in a pram or stroller. If you want to add entry to the Duomo di Siena, that's an optional €12 ticket you can book at checkout. The whole thing stays under 12 people, which is why the pace never feels rushed and the guide can actually answer questions about the places you're standing in.

What’s included

• Awarded gelato tasting with three organic flavors.
• wine tasting with local and regional sparkling wines including Prosecco.
• full lunch at a traditional osteria with homemade pici pasta, pecorino cheese, cold cuts, bruschetta with extra virgin olive oil, ricciarelli biscuits and Chianti or white wine.
• licensed English-speaking tour guide.
• small group capped at 12 people.
• vegetarian options throughout.

Before you book

Days and timesNext departure: 16 Mar 2027

Book up to1d before

AgesAdult (18 to 75 years) · Child (3 to 17 years) · Under 3: can't be booked

GroupUp to 12

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.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated yesterday

Good to know

Low physical effortStroller-friendlyPets welcomePublic transport nearbyNot recommended during pregnancyNot recommended with heart problems

Operated by Moro Tuscany Tours

Is this one for you?At 2.5 hours, this tour fits into a morning or afternoon without consuming your whole day, which means you can pair it with other Siena plans or simply move on to another town by evening. The small group size and licensed guide make it work for families with young children and for travelers who want actual conversation about the places you're walking through, rather than a rushed procession through checkpoints.

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Top questions

Can children come?

Yes. Ticket types: Child (3 to 17 years). Children under 3 can't be included in the booking.

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

How long does this Siena walking tour actually take?

The tour runs 2.5 hours total, which leaves room for other plans in the morning or afternoon depending on when you book your departure time.

What exactly do I eat and drink on this tour?

You taste three organic gelato flavors at an award-winning shop, sample local and regional sparkling wines like Prosecco near Piazza del Campo, and sit down to a full lunch of homemade pici pasta, pecorino cheese, cold cuts, bruschetta with extra virgin olive oil, ricciarelli biscuits and either Chianti or white wine at a traditional osteria.

What is Piazza Salimbeni and why does the tour stop there?

Piazza Salimbeni is home to the Palazzo Pubblico, the oldest bank in the world, which has been operating continuously since 1472. The tour includes a stop to see it and learn its history.

Are vegetarian options available?

Yes, vegetarian options are available throughout the tour, including at the osteria lunch.