Val d'Orcia wine tour from Siena: Brunello and Nobile tastings

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Free cancellationTravelers' pick

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Duration10h–11h

GroupUp to 55

LanguagesEN · IT +1

Mobile ticketAccepted

Montepulciano and Montalcino are wine towns built on hilltops, and you taste each wine where it is made.

A full-day wine tour from Siena through Val d'Orcia visits three towns—Montepulciano, Pienza and Montalcino—with two wine tastings, lunch with cured meats and pasta, and free time to walk each town's historic streets. A multilingual guide leads the group by minivan, and wine tastings are held in English with translation support when needed. The tour runs 10 to 11 hours and departs from Siena Railway Station.

10h–11h

Step-by-step itinerary

Tuscany wine tour and tastings

Meet staff at Siena Station
Travel by minivan to Montepulciano
Explore Montepulciano streets and viewpoints
Wine tasting and cellar visit in Montepulciano
Free time in Pienza for sightseeing and shopping
Wine tasting and cellar visit in Val d'Orcia
Explore Montalcino and local shops
Wine tasting with Brunello and snacks in Montalcino
Return to Siena

The Experience

You meet the staff outside Siena Railway Station at the clock tower, then travel by minivan through the Val d'Orcia—a UNESCO-designated landscape of olive groves, vineyards and cypress trees. The route takes you to Montepulciano first, where you have free time to walk its historic streets and scenic viewpoints before tasting Nobile di Montepulciano in a wine cellar. That same wine appears again at lunch: cured meats, cheeses, pasta with traditional Tuscan ragù, and water and coffee round out the meal.

Pienza comes next, a Renaissance town famous for its pecorino cheese and architecture. You have time to explore on your own—shops, viewpoints, the town itself—before the group moves on to a second wine tasting in the Val d'Orcia itself. Here you taste Rosso di Montepulciano and see the landscape that produces it. The final stop is Montalcino, another hilltop town, where you taste Brunello di Montalcino paired with local snacks and have time to browse its streets and regional shops. The minivan returns you to Siena after the day ends.

A moderate amount of stairs and walking is involved, and the itinerary may shift depending on special events or opening hours, though all three towns will be visited. Wine tastings take place in English, with your guide providing translation in Spanish or Italian as needed. Infants can ride in a pram or stroller, and specialized infant seats are available.

What’s included

Two wine tastings featuring Brunello di Montalcino and Nobile di Montepulciano in their home towns.
lunch with cured meats, cheeses and pasta with traditional Tuscan ragù.
water and coffee.
free time to explore Montepulciano and Pienza on your own.
minivan transport from Siena through Val d'Orcia.
a multilingual guide in English, Spanish or Italian.

Good to know

Easy physical levelStroller friendlyInfant seats availablePublic transport nearbyInfants must sit on laps

Operated by myTour in Italy

Is this one for you?Pick summer for warm weather and outdoor tastings, or winter for fewer crowds—both visit the same wineries and include tastings in Pienza and Montepulciano with lunch included.