Val d'Orcia: Brunello & Montepulciano Wine Day Trip

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.

Step-by-step itinerary

Stops and time spent at each3 stops

1. Montalcino1h 30m
2. Montalcino Fortress15m
3. PienzaEntry included1h 30m

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.

Options for this experience

2 options

Brunello wine tour of the Val d'Orcia, visiting Montalcino and MontepulcianoGuide in English · 08:00

Private tour, departing from FlorenceGuide in English · 08:00

You'll see the exact price of each option when you check availability.See dates and prices

Before you book

Lasts 10h 30m, runs every day at 08:00, from € 229 per person, with a live guide in English, in groups of up to 8 and with free cancellation up to 24 h before.

Days and timesEvery dayDeparts at 08:00

Book up to1h before

AgesAdult (13 and older) · Child (6 to 12 years) · Infant (under 6)

GroupUp to 8

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

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

Prices and times updated yesterday

Good to know

Low physical effortStroller-friendlyInfant seats availablePublic transport nearby

Operated by Keys Of Italy / Florence

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Top questions

Can children come?

Yes. Ticket types: Child (6 to 12 years); Infant (under 6).

How long is the Val d'Orcia wine tour from Florence?

The day trip lasts around 10 hours including travel time between Florence, Montalcino, Pienza, and Montepulciano.

Is lunch included on this Brunello wine tour?

Yes, a three-course lunch with wine is included in Pienza (served outdoors April-October or indoors November-April).

Do you visit actual wineries during this day trip?

Yes, there’s a guided visit and tasting at a family-owned winery in Montalcino plus an underground cellar tour in Montepulciano.

Are there vegetarian options for lunch?

The reference doesn’t specify but most Tuscan restaurants can accommodate vegetarians if requested ahead.

Is hotel pickup included for this Tuscany wine tour?

No hotel pickup is mentioned. Departure point is central Florence with premium minivan transport provided.

How many people are on each tour group?

The semi-private tour has a maximum of 8 people per group.

What makes this day trip different from other Tuscany tours?

This tour includes tastings of Brunello di Montalcino and Nobile di Montepulciano wines plus lunch in Pienza and cellar visits.