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Val d'Orcia: Wine Tasting Day Trip & Gladiator Fields

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Free cancellationTravelers' pick

1/47

Duration11h 30m

GroupUp to 45

LanguagesEN · PT +1

Mobile ticketAccepted

Brunello sips in Montalcino, cheese in Pienza, rolling hills everywhere

You’ll taste Brunello wines in Montalcino cellars, climb fortress walls for sweeping views of Val d’Orcia’s hills, sample pecorino cheese in sunlit Pienza streets, and walk through real-life Gladiator fields with your guide sharing stories along the way. Expect laughter over shared snacks and quiet moments where Tuscany just sinks in.

11h 30m

Step-by-step itinerary

Meet guide at Piazzale Montelungo
Drive two hours to Val d'Orcia
Explore Montalcino medieval streets
Visit Brunello winery and taste wines
Free time for lunch and fortress visit
Arrive in Pienza and explore town
Visit Pienza Cathedral
Drive by Madonna di Vitaleta chapel
See Gladiator film locations
Visit Montepulciano and wine tasting
Return to Florence by bus

The Experience

The first thing I noticed was the way the bus windows fogged up as we left Florence behind—someone wiped a circle clear just in time to catch the first patchwork of Val d’Orcia’s hills. Our guide, Lucia, had this habit of pausing mid-sentence to point out a cypress line or a crumbling farmhouse. She said she grew up nearby and you could tell—she pronounced Montalcino like it was a secret. The drive wasn’t short (maybe two hours?), but honestly I didn’t mind. The air started to smell different somewhere past Siena—like cut grass and something faintly sweet, maybe wildflowers.

Montalcino itself felt like walking into an old movie. Cobblestones underfoot, people chatting outside cafes even though it was barely noon. Lucia led us to a Brunello winery where the owner poured wine into glasses that looked too thin for my clumsy hands. I tried swirling it like everyone else but mostly just watched the light catch the red. We nibbled sheep’s cheese (pecorino—sharp, salty), and someone asked about the barrels lining the cellar walls. The winemaker answered in Italian first, then smiled and switched to English for us. I still think about that cellar—cool stone, smells of wood and grape skins.

We had free time after that. I wandered up to Montalcino’s fortress because Lucia said the view was worth it. She wasn’t wrong—the wind up there nearly stole my hat but you could see vineyards stretching forever, little roads curling between them. Lunch was simple: bread, more cheese, tomatoes so ripe they almost fell apart when you touched them. I heard church bells somewhere below.

Pienza came next—a Renaissance town rebuilt by some pope (Lucia told us his name but I forgot). The streets were narrow and sun-warmed; at one point I ducked into a shop just for the smell of fresh ricotta. There was this moment outside the cathedral where everything went quiet except for a couple laughing over gelato on the steps. Later we drove past those “Gladiator” fields—someone played the movie soundtrack on their phone and everyone groaned but also kind of loved it.

Last stop: Montepulciano for Vino Nobile tasting in another ancient cellar (this one smelled more earthy than fruity). The snacks were local stuff—olives, bread with olive oil—and our group lingered longer than planned because nobody really wanted to leave yet. On the way back to Florence, Lucia dozed off in her seat and someone passed around leftover cheese wrapped in napkins. Not every day feels this full—you know?

What’s included

Your day includes round-trip travel by comfortable coach with WiFi from Florence, guided visits through historic towns like Montalcino and Montepulciano with wine tastings (Brunello and Vino Nobile), pecorino cheese pairings along the way, plenty of free time for exploring or grabbing lunch at your own pace, plus stories from your expert multilingual guide before returning by early evening.

Good to know

Moderate physical levelStroller friendlyInfant seats availablePublic transport nearbyNot for heart conditionsInfants must sit on laps

Operated by Ciao Florence Tours Srl