Private Guided Tour of Montepulciano with Wine Tasting

Underground into the ancient wineries of Montepulciano

A private guided tour of Montepulciano takes you through the Renaissance "pearl" of Tuscany—from the Piazza Grande at the summit down winding streets lined with palaces and churches, then underground into one of the town's oldest wineries for a tasting of Nobile wine. The guide speaks English and the tour runs two hours, with flexible scheduling available by request.

Step-by-step itinerary

Explore Montepulciano and wine tasting

• Visit Piazza Grande and Cathedral
• See Government Palace and Renaissance palaces
• Enjoy panoramic views over valleys
• Descend main street admiring palaces and churches
• Learn about local traditions and movie sets
• Tour ancient winery underground
• Taste Nobile wine

The Experience

Montepulciano sits high on a ridge, and the tour starts at the top. You begin in the Piazza Grande, the main square where the never-finished Cathedral, the Government Palace, and the Palaces Contucci and Tarugi frame the space. A 1500 well stands in the center. From there you look out over the Val di Chiana and part of the Val d'Orcia—two valleys that stretch toward the horizon. The guide points out the architectural details that mark the Renaissance, and explains what makes this town different from the villages around it.

From the summit you descend the main street, which winds through the town in a way that reveals palaces and churches as you walk. The guide shows you the less-known corners, the best Renaissance facades, and the panoramic terraces. Along the way you learn about local traditions—like the barrel-pushing competition held once a year—and spot the movie sets filmed here. The walking is steady but not steep; the town is built on a slope, so descent is easier than ascent.

The tour ends underground. You visit one of the ancient wineries carved into the rock beneath the town and taste a glass of Nobile wine, the local red that defines the region. The winery itself is part of the experience—the stone walls, the age of the space, the way wine has been stored here for centuries. The tour runs two hours total. Scheduling is flexible; while the standard times are 10am and 3pm, you can arrange a different time directly with the guide.

What’s included

Private guided tour of Montepulciano with a live English-speaking guide; a glass (or more) of Nobile wine tasted in an ancient underground winery.

Good to know

Easy physical levelStroller friendlyPets welcomePublic transport nearby

Operated by Chiara Fanti - Guida Turistica Siena

Is this one for you?Book this if you want a private guide to set the pace through Renaissance palaces and down Montepulciano's main street, rather than navigating the descent and stops on your own.

Traveler reviews

4.88★★★★★★★★★★

17 verified traveler reviews

Read all the reviews ›

Top questions

What is the Piazza Grande and why does the tour start there?

The Piazza Grande is the main square at the summit of Montepulciano, where the never-finished Cathedral, Government Palace, and Renaissance palaces Contucci and Tarugi stand. The tour starts there because it is the highest point in town and gives you the full view of the Val di Chiana and Val d'Orcia before you descend.

Do I walk the whole tour, or is there transport through the town?

You walk through Montepulciano. The tour descends the main winding street on foot, moving through the palaces and churches. The descent is easier than climbing, and the route is suitable for all fitness levels, though strollers and prams are welcome if you are traveling with infants or small children.

What kind of wine do I taste, and where?

You taste Nobile wine, the red wine produced in the Montepulciano region. The tasting happens underground in one of the ancient wineries carved into the rock beneath the town, where wine has been stored for centuries.

Can I choose a different time than 10am or 3pm?

Yes. The standard tour times are 10am and 3pm, but you can arrange a different departure time directly with your guide upon request.

Is the guide English-speaking?

Yes, the guide speaks English and leads the tour privately, just for your group.