Siena walking tour with lunch & Chianti wine tasting

★★★★★★★★★★ 4.81 (101 reviews) 86% rated it 5 stars

Free cancellationLikely to sell out

1/23

Duration2h 30m

GroupUp to 12

LanguagesEN

Mobile ticketAccepted

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.

2h 30m

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.

Good to know

Easy physical levelStroller friendlyPets welcomePublic transport nearbyNot for pregnant travelersNot for heart conditions

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.