The 5 Best Montalcino & Val d’Orcia Day Trips

1.Full Day Tour to Val d’Orcia and Gladiator’s Fields with Wines

★★★★★★★★★★4.5 · 1,106 reviews · 11 hours 30 minutes (approx.) · from $94Our pick

Travel by air-conditioned coach from Florence to Montalcino, Pienza, and Montepulciano with an English-speaking guide. Expect two winery visits, Brunello and Vino Nobile tastings, pecorino cheese, free time in each town, and a quick look at the Gladiator filming area.

“We had a really good experience - it was a great way to see lots of the Val D’Orcia in a day. Tabatha was a really knowledgeable helpful guide and gave the best places to get food so we had a lovely picnic in Pienza. The ancient cave for the second winery was really cool to see.”

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2.Val D’Orcia Tour with Wine Tasting

★★★★★★★★★★4.6 · 1,106 reviews · 11.5 hours · from $108

Spend 11.5 hours in Val d’Orcia with stops in Montalcino, Pienza, and Montepulciano. You’ll taste Brunello and Vino Nobile, sample Pecorino cheese, and hear local stories from guides such as Alex, Julia, and Constantino. Comfortable coach transport keeps the day simple.

“I had a wonderful one-day trip to Val d'Orcia. The views were amazing – beautiful hills, vineyards, and small towns like Pienza and Montalcino. Our guide, Jan, was great! He was very friendly and knew a lot about the area. He made the trip fun and relaxing, and he shared interesting stories and local tips. It was a perfect day in the Tuscan countryside. I highly recommend this tour”

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3.Val d’Orcia Brunello Wine Tour with Montalcino and Montepulciano

★★★★★★★★★★4.5 · 359 reviews · 10 hours 30 minutes (approx.) · from $277

Spend 10.5 hours exploring Montalcino, Pienza, and Montepulciano from Florence in a luxury air-conditioned van. Taste Brunello and Vino Nobile, tour a vineyard and ancient cellar, enjoy a three-course lunch, and travel with no more than eight people. Drivers such as Simona, Luca, Mike, and Salvo share local history along the way.

“We had a wonderful trip with Luca as our driver. There was so much to see and learn and it was just what I’d hoped for.”

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4.Valdorcia Wine, Brunello Montalcino, Montepulciano

★★★★★★★★★★4.8 · 238 reviews · 10.5 hours · from $265

Spend 10.5 hours in Val d’Orcia with an English-speaking driver and a group capped at eight. Visit a family winery near Montalcino, taste Brunello, enjoy a three-course lunch in Pienza, and explore Montepulciano’s underground cellars with wine, olive oil, and local foods.

“What a wonderful day! Mike, our driver, was so nice and provided some great history along the drive. We never felt rushed by him. The wineries and towns were spectacular. I would absolutely recommend this tour to others!”

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5.Olive Oil Tours and Tasting at Frantoio di Montalcino

★★★★★★★★★★5.0 · 85 reviews · 1 hour 30 minutes (approx.) · from $60Best value

At Frantoio di Montalcino, guides such as Daniel and Alisha explain how olives become extra virgin oil, from grove to bottle. In a small group of up to 12, you will tour the mill, taste several oils and EVOO condiments with warm bread, then shop for bottles to take home.

“The tour was informative about their production facilities, how they make olive oil, and the differences between olive oils.”

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