Brunello di Montalcino Wine Tour: Montepulciano & Val d'Orcia

Taste Brunello at a working winery, then walk the hilltop towns that frame it

A small-group wine experience in Montepulciano, Montalcino and Val d'Orcia pairs a guided lunch and tasting of Brunello di Montalcino at a boutique winery-farm with visits to two medieval hilltop towns and a UNESCO landscape. You cross the Chianti hills and the fourteenth-century fortress of Montalcino, taste the cellars and regional specialties, then explore Montepulciano's Renaissance streets and optional second winery on the way back.

Options for this experience

2 options

From € 215 to € 249 per person, depending on the option and date you choose. See options & prices

Montalcino and Montepulciano VIP wine experience, including lunch Available from 15 Mar 2027 Guide in English

Complete tour plus a second winery visit Available from 15 Mar 2027 Guide in English Nobile wine tasting in Montepulciano, where you can enjoy it.

None of these options right for you? See 7 alternatives ›

Step-by-step itinerary

Tuscany wine tour and sightseeing

• Cross Chianti hills and Monteriggioni
• Visit Montalcino winery and lunch tasting
• View Val d'Orcia and Gladiator movie sites
• Explore Montepulciano town and wine cellars

Stops and time spent at each 4 stops

1. Monteriggioni passing by
2. Montalcino 1h 30m
3. Val d'Orcia passing by
4. Montepulciano 1h

What’s included

• Organic food, Pecorino cheese and extra-virgin olive oil.
• a guided lunch at a boutique winery with panoramic views.
• bottled water throughout the day.
• a licensed tour guide in English for the full day.
• small-group experience with a maximum of six people.
• tastings of Rosso di Montalcino, Brunello di Montalcino and Super Tuscan wines.
• a visit to the wine cellars.
• and a photo service to capture the landscape and moments.

Times

7 similar tours departing soon ›

Next departure: 15 Mar 2027

Information

Taste Brunello di Montalcino at a boutique winery with guided lunch in the heart of Tuscany.

Group Up to 6 · max 4 per booking 1 similar private tour ›

Live guide English Another language? ›

Meeting point and pickup No hotel pickup: you go to the meeting point. Ends at a different place from where it starts. 1 similar tour with pickup › See the exact address

Book up to 1d before

Ages Adult (18 to 75 years) · Under 18: can't be booked

Cancellation and refunds Free 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.

Good to know

Low physical effort Stroller-friendly Infants must sit on laps

More information The exact meeting point address, the operator’s instructions and every other detail are in the full listing. See the full listing

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The experience

Montepulciano sits 600 metres above sea level between two valleys, and the day starts by crossing the Chianti hills toward Montalcino's fortress, which commands views over Val d'Orcia. At a boutique winery-farm there, you sit down to a guided lunch pairing Rosso di Montalcino, Brunello di Montalcino and Super Tuscan wines with organic food, Pecorino cheese, extra-virgin olive oil and homemade dessert. After the meal, you walk the cellars and have time to rest on the grounds before moving on.

The route then crosses the Val d'Orcia, a UNESCO heritage landscape of cypress-dotted hills, ancient villages and Etruscan-origin farms that line the Via Francigena pilgrimage road. This is the terrain where Gladiator was filmed. You stop to photograph the panoramic views, then drive the short distance to Montepulciano itself, where you walk the steep Renaissance streets inside the medieval walls, visit the historical wine cellars and admire the palaces. If you choose the second-winery option at checkout, you add a tasting of Nobile di Montepulciano wine before heading back.

The group stays under six people throughout, and a licensed English-speaking guide stays with you for the full day. Water is provided, and the pace lets you linger at each stop without rushing between them.

Top questions

What is Brunello di Montalcino and why is it famous?

Brunello di Montalcino is a red wine from the Montalcino region that Wine Spectator has listed among the best wines in the world. You taste it at the winery where it is made, paired with a full lunch of local food and regional wines.

Do I get to see inside the wine cellars?

Yes. After your guided lunch and tasting at the boutique winery-farm, you visit the cellars where the wine is aged, then have leisure time to walk the grounds and vineyards.

What are the two towns I visit on this tour?

You visit Montalcino, a medieval hilltop town crowned by a fourteenth-century fortress with views over Val d'Orcia, and Montepulciano, a Renaissance town enclosed by fortified walls perched on a hill between two valleys. Both are stops on the same day, with lunch at a winery in between.

Can I add a second winery to taste Nobile di Montepulciano?

Yes. The standard tour includes one winery and lunch there. At checkout, you can choose the option that adds a second winery visit and a tasting of Nobile di Montepulciano wine before the return to Montepulciano.

Is Val d'Orcia the landscape from the Gladiator movie?

Yes. Val d'Orcia, a UNESCO heritage site, is the hilly terrain where Gladiator was filmed. The tour crosses this landscape of cypress-dotted hills, ancient villages and farms, with stops to photograph the panoramic views.

Operated by Moro Tuscany Tours. Explorevia does not run this tour: we compare it with similar options, and you book it with our booking partner.

Prices and times updated 8 days ago