Chianti & Brunello wine tour from Siena: Small group, 2 wineries

Two family wineries, Tuscan lunch, and the Val d'Orcia landscape in one day

A small-group wine tour from Siena visits two family-owned boutique wineries in the Chianti and Montalcino regions, with tastings of Chianti Classico and Brunello di Montalcino, a Tuscan lunch with homemade pasta and Pecorino cheese, and a drive through the UNESCO Val d'Orcia to Pienza. Maximum six travelers per group. A licensed guide leads in English or Italian.

Step-by-step itinerary

Stops and time spent at each

1. Montalcino1h
2. Val d'Orciapassing by

Wine tasting and sightseeing in Tuscany

• Introduction to Siena's history viewpoint
• Visit organic boutique winery and lunch
• Tour family owned Brunello winery
• Drive through Val d'Orcia UNESCO site
• Explore picturesque town of Pienza

The experience

The day starts with an introduction to Siena's history from a panoramic viewpoint overlooking the city, then moves into the Chianti region. At the first winery (an organic, family-owned estate) you'll taste Chianti Classico surrounded by Tuscan hills, tour the historical cellars, and sit down to a Tuscan lunch with homemade pasta, Pecorino cheese, cold cuts, and bruschetta. The second stop is a family winery in Montalcino, where you taste Brunello di Montalcino (ranked best wine in the world in 2023), explore the cellars, and learn how the wine is made. Between tastings you'll also sample extra virgin olive oil.

The route then carries you through the rolling hills of Val d'Orcia, a UNESCO site where the Gladiator film was shot, and ends in Pienza: a Renaissance town known for its architectural harmony and Pecorino cheese tradition. The group stays under six people, so there's no crowded bus or rigid schedule. The pace is relaxed and you meet the winery owners and staff directly.

What’s included

• Small group of maximum six travelers.
• tour of two family-owned winery cellars with historical background.
• tastings of Chianti Classico, Brunello di Montalcino and Super Tuscan wines.
• extra virgin olive oil tasting.
• Tuscan lunch with homemade pasta, Pecorino cheese, cold cuts and bruschetta.
• licensed tour guide in English or Italian.
• drive through Val d'Orcia UNESCO site and stop in Pienza.

Before you book

Days and timesNext departure: 19 Mar 2027

Book up to1d before

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

GroupUp to 6 · max 4 per booking

Live guideEnglish and Italian

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 8 days ago

Good to know

Moderate physical effortStroller-friendlyPets welcomePublic transport nearbyNot recommended during pregnancyNot recommended with heart problemsNot recommended with back problems

Operated by Moro Tuscany Tours

Is this one for you?A small group suits travelers who want to avoid crowded buses and meet the winery owners directly, rather than follow a strict itinerary with dozens of other visitors. The relaxed pace and two-winery focus let you linger over tastings and lunch without rushing to the next stop.

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Top questions

What languages is the tour guided in?

Live guide in English and Italian.

What wines do I taste on this tour from Siena?

You taste Chianti Classico at the first winery and Brunello di Montalcino at the second, along with Super Tuscan selections and extra virgin olive oil. Both are family-owned estates where the guide explains the winemaking process and the region's traditions.

Is lunch included in the tour price?

Yes. A Tuscan lunch is served at the first winery and includes homemade pasta, Pecorino cheese, ham, salame, and bruschetta.

How many people travel together on this tour?

The group is capped at six travelers, so you avoid large bus tours and get personal attention from the guide throughout the day.

What is Val d'Orcia and why do we stop there?

Val d'Orcia is a UNESCO-listed landscape of rolling Tuscan hills between Montalcino and Pienza. The route passes through it on the way to the final stop in Pienza, and it's the location where scenes from the film Gladiator were shot.