Val d'Orcia: Brunello & Montepulciano Wine Day Trip

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Duration10h 30m

GroupUp to 8

LanguagesEN

Mobile ticketAccepted

Winding tuscan roads vineyards pecorino cheese and old cellars

You’ll wind through Val d’Orcia’s rolling hills with a small group, sipping Brunello in Montalcino, tasting Pecorino cheese over lunch in Pienza’s garden (or cozy indoors), and exploring Montepulciano’s ancient cellars with local stories along the way. Expect laughter, earthy scents, good wine—and maybe a view you’ll keep thinking about long after you’re home.

10h 30m

Step-by-step itinerary

Val d'Orcia Wine and Cheese Tour

Meet English speaking driver
Visit family winery in Montalcino
Learn about Brunello wine process
Wine tasting of different vintages
Stop at Montalcino castle and city centre
Arrive in Pienza for lunch
Enjoy 3-course meal with wine
Free time to explore Pienza town
Tour historical cellar "The underground city"
Wine and food tasting at cellar exit
Visit Montepulciano main square
Return to Florence

The Experience

The first thing I remember is the way the morning light hit the hills outside Florence—soft, kind of golden, like someone had turned down the world’s contrast. Our driver, Luca, was already joking before we’d left the city. He pointed out cypress trees lined up like little soldiers as we rolled into Montalcino. I could smell fresh earth when we stepped out at the first winery—a family place where Nonna waved from her kitchen window and the barrels felt cool to touch. Tasted Brunello for the first time there (I tried to swirl it like they do on TV—spilled a drop on my shoe, classic).

We wandered through Montalcino’s fortress after that. It’s smaller than I’d pictured but you can see forever from up there—vineyards stitched across the valley, some old guy fixing his bike in the square below. By lunchtime we were in Pienza, eating pecorino and pasta in what used to be a convent garden (the waiter said April to October is best for sitting outside—inside was still cozy though). The cheese shops smelled sharp and sweet at once. I tried to say “cacio” right; Luca laughed and shook his head.

The last stop was Montepulciano’s underground cellars—dark stone tunnels with dust motes floating in shafts of light. There was this moment where everything went quiet except for our footsteps and someone uncorking a bottle somewhere nearby. We tasted Nobile di Montepulciano at street level after climbing back up; it tasted warmer than I expected. Honestly, I didn’t want to leave yet but traffic waits for no one, so yeah… if you go, take your time with each glass.

What’s included

Your day includes premium minivan transport from Florence with air conditioning and water provided by your English-speaking driver.
You’ll enjoy guided tours at two wineries—with tastings of Brunello di Montalcino and Nobile di Montepulciano—plus food pairings.
Lunch is served in Pienza (outdoors when possible), followed by free time to wander historic towns before returning to Florence by evening.

Good to know

Easy physical levelStroller friendlyInfant seats availablePublic transport nearby

Operated by Keys Of Italy / Florence