Val d’Orcia Day Trip from Florence: Tuscany’s Most Scenic Villages

Be warned: this is an early start kind of day. Pick-up is usually around 7:00 AM, and they are not joking about punctuality . Be late and the bus will leave without you. Coffee first, excuses later.

A breathtaking view of rolling hills of Val D’Orcia, Tuscany

Today’s adventure takes us away from Florence and straight into the heart of Tuscany: Val d’Orcia, a UNESCO World Heritage Site and one of the most beautiful regions in Italy.

All our stops were classic Renaissance towns, and the journey itself was super comfortable thanks to a fully air-conditioned coach. We visited in October, which honestly felt perfect — warm mornings, crisp evenings, and those golden Tuscan colours everywhere.

Bonus Tip: Most day tours depart from Piazza del Popolo, which isn’t just a meeting point, it’s a piece of history!! This square was once the grand entrance to ancient Rome. Travelers from across the world entered the city through this route, greeted by magnificent architecture. The square is adorned with stunning cathedrals and, right at its center, an imposing Egyptian obelisk that was brought to Rome centuries ago. It’s a jaw-dropping welcome to the Eternal City!

Stop 1: Montalcino & Brunello Dreams 🍷

Our first stop was Montalcino, home of the world-famous Brunello di Montalcino wine. We visited Padaletti Winery, known as the first family to ever produce Brunello. So yes, history was flowing freely along with the wine.

Walking through Montalcino felt like stepping back in time. Cobblestone streets, stone buildings, and that quiet, artsy charm that makes you slow down without even realising it. The town is quaint, cozy, and effortlessly elegant.

The wine tasting here was outstanding, and I highly recommend not skipping it. We even brought back a bottle of Brunello 2019 Reserve, considered one of the best years for Montalcino wines and award-winning too. No regrets. None.

Stop 2: Pienza – Gelato, Views & Pasta 🍦

Next up was Pienza, another Renaissance gem and arguably the best place to just… wander. There isn’t a long checklist of things to do here and that’s the beauty of it.

Grab a gelato, stroll through the streets, and soak in the breathtaking views of the rolling Tuscan hills. You’ll need under an hour to explore the town properly. It’s small, charming, and very photogenic.

A quick heads-up: there are quite a few tourist-trap restaurants here with eye-watering prices. We chose one of the more reasonably priced options:📍 Baccano Il Panino Toscano

While still a bit pricey, it was worth it for the experience. We tried Pici pasta, a thick hand-rolled Tuscan pasta that Pienza is famous for and I’d absolutely recommend giving it a go.

Stop 3: Montepulciano – Wine in a Dungeon 🧀🍷

Our final stop was Montepulciano, another Renaissance town, similar in vibe to Montalcino but slightly smaller. The real highlight here, though, was the wine and cheese tasting.

The winery was built in Etruscan-style underground caves, deep beneath the town, basically a real wine dungeon. Cool, atmospheric, and completely unique.

Here, we tasted Vino Nobile di Montepulciano, another iconic Tuscan red, paired with Pecorino cheese of different ages (young, aged, very aged). If you love wine and cheese, this alone makes the trip worth it. Naturally, as collectors, we couldn’t leave empty-handed and another bottle joined our suitcase.

Final Thoughts

Is the Val d’Orcia Day Tour Worth It?

Absolutely. 100%.

• ⏱ Duration: ~10 hours

• 💶 Cost: Around €45 per person

• 🍷 Includes: Transport, town visits, wine tastings & cheese pairing

• 📸 Vibes: Rolling hills, medieval towns, slow Tuscan life

For the price, this tour is incredible value and an easy way to experience the best of Tuscany without renting a car or planning logistics yourself.

We highly recommend this day tour from Florence.

Tour operator we used: Val d'Orcia Full Day Tour from Florence: wine and food tour

If you’re in Florence and have a day to spare, this trip is a must. It’s history, culture, and coastal beauty rolled into one unforgettable experience. Just remember: early start, comfy shoes, and an empty stomach for all that Wine! Happy travels!