Chianti Classico & Brunello Wine Tour from Siena, 2 Wineries

Two wineries instead of one bus stop, and a vehicle that holds six instead of forty.

A small-group wine tour from Siena through Chianti Classico and Val d'Orcia, visiting a boutique family-owned winery for tastings paired with Pecorino cheese, cured meats and olive oil, then either Montalcino's fourteenth-century fortress or a second Brunello winery. Maximum six travelers share one private vehicle and a licensed guide who speaks English or Italian.

Step-by-step itinerary

Stops and time spent at each

1. Val d'Orciapassing by
2. Montalcino1h 30m

Chianti Classico and Montalcino tour

• Visit organic boutique winery
• Taste wines and Tuscan products
• Drive through Chianti Classico region
• Admire panoramic views to Montalcino
• Visit Montalcino fortress and village

The experience

Five and a half hours means you move at your own pace instead of keeping to a bus schedule. The tour starts at a boutique winery in Chianti Classico, where you taste wines from the region and walk through medieval cellars while learning how the winemaker produces them. Pecorino cheese, ham, salame, bruschetta and extra-virgin olive oil come with the tasting, eaten in the winery's atmosphere overlooking Tuscan hills and cypress trees.

From there, the drive to Montalcino crosses Val d'Orcia: olive groves, castles and the landscape that appears in Renaissance paintings. At the end, you choose: visit Montalcino's fortress, a fourteenth-century structure with boundary walls and towers that opens onto views across the valley, or upgrade to a second winery for a Brunello tasting instead. Either way, the licensed guide travels with the group the whole time, and nobody waits for stragglers or sits through a sales pitch.

The vehicle holds a maximum of six people, so you travel with your own party or a couple of other travelers, not a crowd. Children from age one ride along. Infant seats are available. Public transport runs nearby if you prefer to meet the group at the winery rather than arrange a separate pickup.

What’s included

• Chianti Classico and Super Tuscan wine tastings.
• tour of the historical cellars.
• Pecorino cheese, cured meats, bruschetta and extra-virgin olive oil paired with the tasting.
• licensed tour guide in English or Italian.
• private vehicle for up to six travelers.
• Brunello di Montalcino wine if you choose the second winery option.

Options for this experience

2 options

Small group tour of 1 boutique wineryGuide in English · 14:00Travel in a premium van

Add a second winery in MontalcinoGuide in English · 14:00

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

Before you book

Days and timesTuesdayDeparts at 14:00

Book up to1d before

AgesAdult (18 to 75 years) · Child (1 to 17 years): free

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 today

Good to know

Low physical effortStroller-friendlyInfant seats availablePublic transport nearby

Operated by Moro Tuscany Tours

Is this one for you?The small group and private vehicle mean you set the pace instead of following a strict schedule, and you taste wines in the cellar itself rather than at a tasting room. Choose the second winery option if Brunello is what you came for. Pick the Montalcino fortress if you want the medieval village and the valley views.

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Top questions

What languages is the tour guided in?

Live guide in English and Italian.

Can children come?

Yes. Ticket types: Child (1 to 17 years): free.

What's the difference between visiting Montalcino and choosing the second winery instead?

Montalcino is a medieval village with a fortress offering panoramic views into Val d'Orcia. The second winery option replaces the village visit with a Brunello wine tasting at a boutique estate. You pick one or the other at checkout.

What wines do you actually taste on this tour?

Chianti Classico and Super Tuscan wines at the first winery are included in every tour. Brunello di Montalcino is only available if you choose the second winery option.

Does the guide stay with the group the whole time?

Yes, a licensed tour guide in English or Italian travels with the group throughout the five and a half hours, explaining the region's history and the winemaking process at the cellars.

What food comes with the wine tasting?

Pecorino cheese, ham, salame, bruschetta and extra-virgin olive oil are paired with the wines at the first winery. These are Tuscan products, not a full meal.