Val d'Orcia tour from Siena: Montalcino, Pienza, Montepulciano

Three Tuscan wine towns and a Papal village in one day from Siena

A full-day tour from Siena travels through Val d'Orcia to Montalcino, Pienza and Montepulciano in a small group of up to eight passengers. You taste Brunello at a family-run winery, walk the Montalcino Fortress, eat a three-course lunch in Pienza, then descend into Montepulciano's underground cellar, called "the underground city", for a second wine tasting and local food specialities. An English-speaking driver handles the route while you move between the towns.

Step-by-step itinerary

Stops and time spent at each

1. Montalcino1h 30m
2. Montalcino Fortress15m
3. Pienza1h 30m · entry included

Tour Val d’Orcia highlights

• Meet English-speaking driver
• Visit winery in Montalcino
• Stop at Montalcino castle and city centre
• Enjoy 3-course meal in Pienza
• Tour underground cellar and wine tasting
• Visit Pienza main square
• Return to Siena

The experience

Montalcino arrives first, around 9:45am. A local family runs the winery where you spend time learning how Brunello is made: the vineyard techniques, the fermentation, the aging in barrel, and how to taste different vintages side by side. The stop lasts long enough to move past the feeling of a workplace visit. These are people talking about their own wine. A quick 15-minute stop at Montalcino Fortress and the town center follows, giving you time to photograph the castle and walk the tiny streets before heading downhill.

Pienza sits on the route at 12:15pm, and lunch is a three-course meal in a traditional restaurant, not a rushed stop. The town is famous for Pecorino cheese, and the meal anchors the middle of the day. After eating, you have time to move through the main square on top of the town before the group heads to Montepulciano for the afternoon's second wine experience.

Montepulciano's draw is the underground cellar, a historical space carved beneath a wine shop and called "the underground city" by locals. A guide leads you through it, then greets you at the exit with a wine tasting and local food specialities. You get time to visit the main square afterward and take final photographs before the drive back to Siena, arriving around 6:30pm depending on traffic. The air-conditioned minivan and complimentary water are constants throughout the day.

What’s included

• Guided tour through a family-run Montalcino winery with Brunello tasting across different vintages.
• 15-minute stop at Montalcino Fortress and town center.
• three-course lunch in a traditional Pienza restaurant.
• guided tour of Montepulciano's underground cellar with wine and local food tasting.
• air-conditioned minivan transport.
• complimentary water throughout the day.
• English-speaking driver.

Before you book

Days and timesEvery dayDeparts at 08:30

Book up to1d before

AgesAdult (12 and older) · Child (under 12)

GroupUp to 8

Live guideEnglish

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.

Prices and times updated today

Good to know

Low physical effortStroller-friendlyInfant seats availablePublic transport nearbyNot recommended with heart problems

Operated by Keys Of Italy / Florence

Is this one for you?The full day (roughly 10 to 11 hours from pickup to return) means you see three towns and two wine cellars without arranging separate transport or navigating between them yourself, though it leaves little room for lingering in any one place or adding a fourth destination to your Siena day.

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Top questions

Can children come?

Yes. Ticket types: Child (under 12).

What's the difference between the Brunello tasting in Montalcino and the wine tasting in Montepulciano?

Montalcino's stop is at a family-run winery where you learn the full process of making Brunello (vineyard work, fermentation, aging), and taste different vintages. Montepulciano's experience centers on the underground cellar beneath a wine shop, where a guide shows you the historical space and then you taste wine paired with local food specialities at the exit.

How much free time do you get in each town?

Montalcino Fortress gets 15 minutes for photos and a walk through the town center. Pienza includes a full three-course lunch, which gives you time to eat and explore the main square. Montepulciano offers time to visit the main square after the cellar tour and tasting before departure.

Is the driver also the guide who explains the wine and the cellar?

The driver is English-speaking and handles the route between towns. At the Montalcino winery, the family owners talk you through their Brunello and vineyard. At Montepulciano, a guide leads you through the underground cellar. The driver does not double as the guide.

What happens if I don't drink alcohol?

Travelers under 18 receive non-alcoholic drinks during the tastings. The tour includes food specialities and a three-course lunch regardless, so the experience is not built only around wine.

Can the order of Montalcino and Montepulciano change?

Yes. For operational reasons, the itinerary may swap the order of those two towns, but the stops, tastings and lunch remain the same.