Montepulciano Pienza Montalcino Tour: Medieval Towns

Savor Brunello, Pecorino, and Nobile wines while wandering Tuscany’s charming streets

A full-day private tour from Siena to three medieval villages in the Orcia Valley (Montepulciano, Pienza and Montalcino) with hotel pickup, transport by private vehicle and an English-speaking driver. You'll have free time to explore each town, shop in local stores and taste the regional specialties: Nobile di Montepulciano wine, Pecorino cheese from Pienza and Brunello di Montalcino. Lunch at a reserved restaurant and wine tasting are arranged at the time of booking.

Step-by-step itinerary

Visit Montepulciano, Pienza, and Montalcino

• Drive to Montepulciano
• Explore Montepulciano village
• Drive to Pienza
• Visit Pienza and try Pecorino Cheese
• Drive to Montalcino
• Visit Montalcino fortress
• Enjoy Brunello wine tasting

The experience

The drive from Siena takes you into the Orcia Valley, one of Tuscany's most photographed landscapes. Your first stop is Montepulciano, a medieval hilltop town built around its famous Nobile wine. You'll have time to walk the narrow streets, visit the local wine shops and get a sense of how the town sits above the valley floor. The driver handles the route and the timing. You decide how long to linger.

Pienza comes next, a smaller village known for its Pecorino cheese and Renaissance architecture. The town is compact enough to cover on foot in an hour or two, and the local food shops sell the cheese fresh. From there, the route continues to Montalcino, the day's final stop and home to Brunello, one of Italy's most celebrated red wines. Wine tasting is included here (the winery is booked when you reserve), and you'll have free time to explore the fortress and the town center before the drive back to Siena.

The full day runs eight to nine hours from pickup to drop-off. A reserved restaurant handles lunch, so you're not hunting for a table between stops. Infants and small children can travel in a pram or with specialized infant seats.

What’s included

• Hotel pickup and drop-off in Siena.
• private vehicle transport.
• English-speaking driver.
• all taxes and fees.
• wine tasting at Montalcino.
• lunch at a reserved restaurant.

Before you book

Days and timesEvery dayDeparts at 09:00

Book up to1d before

GroupPrivate

Live guideEnglish

Meeting point and pickupHotel pickup included.You can choose from 3 pickup points.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated 8 days ago

Good to know

Low physical effortStroller-friendlyInfant seats available

Operated by Limo Service in Italy

Is this one for you?Eight to nine hours means you can cover all three towns and the wine tasting without rushing, but the day fills completely. Plan for an early start and a late return to Siena.

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Top questions

What's the difference between the three towns on this tour?

Montepulciano is known for Nobile wine and sits high on a hilltop; Pienza is famous for Pecorino cheese and has Renaissance squares; Montalcino centers on Brunello wine and has a fortress overlooking the valley.

How much free time do I get to explore each town?

You have free time at all three stops to walk around, shop and eat at your own pace: the driver coordinates the schedule and the transitions between towns.

Is wine tasting really included, or do I pay extra?

Wine tasting at Montalcino is included and arranged when you book the tour. Lunch at a reserved restaurant is also arranged at reservation time.

What if I don't want to do the wine tasting or lunch?

Both lunch and wine tasting can be requested or skipped when you make your reservation. You choose what suits your day.

Does the tour include hotel pickup in Siena?

Yes, the driver picks you up at your hotel in Siena and returns you there at the end of the day.