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

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.

Step-by-step itinerary

Stops and time spent at each

1. Val d'Orcia1h
2. Montalcino2h 15m

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.

Options for this experience

2 options

Summer TourGuide in English, Spanish or Italian · 09:45

Winter optionGuide in English, Spanish or Italian · Available from 15 Nov · 09:45

You pick the guide language when booking.

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

Before you book

Days and timesEvery day except Wednesday and ThursdayDeparts at 09:45

Book up to10h before

AgesAdult (13 and older) · Child (3 to 12 years): free · Infant (under 3): free

GroupUp to 55

Live guideEnglish, Spanish 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 yesterday

Good to know

Low physical effortStroller-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.

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Top questions

What languages is the tour guided in?

Live guide in English, Spanish and Italian.

Can children come?

Yes. Ticket types: Child (3 to 12 years): free; Infant (under 3): free.

What wines do I taste on this tour from Siena?

You taste two wines: Nobile di Montepulciano in Montepulciano, and Brunello di Montalcino in Montalcino. Both tastings include visits to wine cellars, and Nobile di Montepulciano also appears at lunch.

How much free time do I have to explore Montepulciano and Pienza?

The itinerary includes free time in both towns to walk their historic streets, viewpoints and shops. The exact duration depends on the day's schedule, but both stops are built in so you can move at your own pace through each one.

Does the tour include lunch?

Yes. Lunch includes cured meats, cheeses, pasta with traditional Tuscan ragù, water and coffee. The meal is part of the full-day itinerary.

What is the Val d'Orcia and why is it on this tour?

Val d'Orcia is a UNESCO-designated landscape in Tuscany filled with olive groves, vineyards and cypress trees. You pass through it on the minivan and stop there for a wine tasting so you can see the countryside that produces the wines you taste.

How long is the tour and where does it start?

The tour runs 10 to 11 hours and departs from outside Siena Railway Station at the clock tower at the main entrance. You return to the same location at the end of the day.