Montalcino Montepulciano Tour: Wine Cheese Tasting

Brunello wine and Pecorino cheese anchor a day through Renaissance hill towns and a working cellar.

A private tour from Siena to Montalcino and Montepulciano covers about 8 hours of driving through Val d'Orcia, a UNESCO World Heritage site known for Tuscan reds and sheep's cheese. You get an hour to explore each medieval village on your own, then a guided cellar tour at a Montalcino winery followed by lunch pairing Brunello with typical Tuscan dishes. Hotel pickup and return are included.

Step-by-step itinerary

Explore Montepulciano and Montalcino

• Pick up from Siena hotel
• Drive through Val d’Orcia scenery
• Visit Montepulciano city
• Free time to explore Montepulciano
• Visit Montalcino medieval village
• Free time to wander Montalcino
• Guided winery cellar tour
• Lunch with Brunello wine pairing
• Return to Siena hotel

The experience

The route threads through rolling hills and cypress-lined roads between two villages that anchor Tuscan wine culture. Montepulciano comes first: a Renaissance city of steep streets and ancient churches where you wander for an hour and catch panoramic views from the top. Montalcino, deeper in the Val d'Orcia hills, follows: a medieval layout of straight, steep streets that open onto views at every turn, and the source of Brunello di Montalcino, one of the world's most recognized wines.

After free time in Montalcino, a local winery hosts the cellar tour and then serves lunch. Dishes pair with their Brunello (the wine the region is built around), and the meal sits at the heart of the day. The guide speaks English, Spanish or Italian, and the tour runs about 8 hours total from hotel pickup to return.

Children from age 3 travel on this tour. Infant seats are available if you need one, and you can flag dietary requirements when you book.

What’s included

• Hotel pickup and return to Siena.
• visits to Montepulciano and Montalcino.
• guided cellar tour at a Montalcino winery.
• lunch with typical Tuscan dishes paired with Brunello wine.
• a live guide in English, Spanish or Italian.

Before you book

Days and timesEvery dayDeparts at 09:00

Book up to1d before

AgesAdult (12 and older) · Child (3 to 11 years) · Under 3: can't be booked

GroupPrivate

Live guideEnglish, Spanish and Italian

Meeting point and pickupHotel pickup is optional; you can also go straight to the meeting point. Ends back at the starting point.You can choose from 20 pickup points.

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 availablePets welcomePublic transport nearby

Operated by Tuscany Private Tour

Is this one for you?Book this as a private tour when you want the two villages and the winery on your own schedule, without sharing the van or the guide's attention. The group size stays at your party only, so the pace and the stops bend to what interests you.

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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 11 years). Children under 3 can't be included in the booking.

What is Brunello di Montalcino and why is the town famous for it?

Brunello di Montalcino is one of the world's most celebrated red wines, produced in the hills around the medieval village of Montalcino in Val d'Orcia. The wine comes from Brunello grapes grown in the region's specific terroir, and the winery you visit on this tour produces it. The cellar tour shows how it is made, and lunch pairs the wine with typical Tuscan dishes.

How much time do I get to walk around Montepulciano and Montalcino on my own?

You have about an hour of free time in each village. In Montepulciano, that hour lets you explore the Renaissance palaces, ancient churches and charming squares, and climb to the top of the steep streets for panoramic views. In Montalcino, the same hour is yours to wander the medieval layout before the winery visit and lunch begin.

Is the winery tour and lunch included in the price, or do I pay extra?

The guided cellar tour at the Montalcino winery and the lunch pairing Brunello with typical Tuscan dishes are both included in the tour price. No separate payment is needed for either.

What does the lunch include, and can I request a different diet?

Lunch pairs typical Tuscan dishes with Brunello wine from the winery. If you have specific dietary requirements (vegetarian, vegan, allergies or other needs), let the operator know when you book and they will arrange it.

Does the tour include a wine tasting before lunch, or only the wine served with the meal?

The winery experience includes a guided tour of the cellar followed by lunch where Brunello pairs with the food. The cellar tour is where you learn how the wine is made. The tasting happens as part of the meal itself.