Val d'Orcia Private Tour: Montalcino, Pienza, Montepulciano

From€545
8 hours
Florence, Italy

About this activity

Experience the beauty of Tuscany's Val d'Orcia region with a private tour of Montalcino, Pienza, and Montepulciano, including guided tours and wine tasting.

Highlights

  • Explore Montalcino's medieval charm
  • Discover Pienza's Renaissance architecture
  • Taste renowned Brunello di Montalcino wine
  • Stroll through Montepulciano's historic center
  • Enjoy scenic views of Val d'Orcia

Full description

Immerse yourself in the enchanting landscapes of Tuscany's Val d'Orcia region on this private tour from Florence. Visit the medieval town of Montalcino, renowned for its Brunello di Montalcino wine, and explore Pienza, a UNESCO World Heritage site celebrated for its Renaissance architecture. Wander through Montepulciano's historic center, famous for its Vino Nobile di Montepulciano. Enjoy scenic drives through rolling hills and vineyards, and indulge in a wine tasting at a local vineyard. This tour offers a perfect blend of history, culture, and gastronomy, providing an unforgettable Tuscan experience.

Included / Excluded

  • Private transportation from Florence
  • Guided tours of Montalcino, Pienza, and Montepulciano
  • Wine tasting at a local vineyard
  • Meals and personal expenses

Important information

Know before you book

  • Tour operates rain or shine; cancellations are not accepted.
  • Wine tasting is included; bring ID if you plan to participate.
  • Children under 18 must be accompanied by an adult.

Know before you go

  • Wear comfortable walking shoes for cobblestone streets.
  • Bring a camera to capture the picturesque landscapes.
  • Check the weather forecast and dress accordingly.

Cancellation policy

Free cancellation up to 1 days before the activity starts

For a full refund, cancel at least 24 hours before the scheduled departure time.

Accessibility

  • Infants Required On Laps
  • Infant Seats Available
  • Stroller Accessible

Traveler reviews

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Honeymoon

I loved it! It was the most amazing views and wine tasting, better than I could have imagined Our tour guide Cristian was very educated on the rich culture and history! My husband and I recommend for honeymoon experience

982genesisgMay 7, 2026TRIPADVISOR

Best honeymoon experience

Great experience with Cristian. He was very patient attentive and fun. He gave a detailed explanation of all the history and culture. We had the best time on our honeymoon!! The views were amazing as well. I highly recommend

christianfJ2949KCMay 7, 2026TRIPADVISOR

Amazing full day in 3 charming towns

We had an absolutely amazing day on the Val d’Orcia private tour visiting Montalcino, Pienza, and Montepulciano. Each town was uniquely beautiful and full of charm, with stunning views of the Tuscan countryside at every turn. The Brunello wine tasting was a true highlight—exceptional wines at a continuous family run vineyard going back 27 generations (1500's). The luncheon at a local farm, complete with thoughtful wine pairings, was equally memorable and gave us a real taste of the region. Although the weather was cold and windy, it didn’t take away from the experience at all—we still fully enjoyed the breathtaking landscapes and atmosphere of these incredible towns. A special thank you to Christian, our driver, who was knowledgeable, friendly, and a true pleasure to spend the day with. This tour was a perfect way to experience Tuscany, and we would highly recommend it to anyone visiting the area.

Elisa_BApr 7, 2026VIATOR

Amazing!!!

A wonderful experience, Driver Alex, amazing, helpful person and in all respects, I highly recommend all their services.

celiofranzoiDec 30, 2025TRIPADVISOR

Top 3 Life Experience

This was a top 3 experience in my entire life. Seeing the country side of Tuscany during the fall with our amazing tour guide Christian took my breath away. Beautiful experience through and through. From our Brunello wine tasting to walking through the streets of Montalcino, Pienza and Montepulciano to Christian’s recommendations at each stop. Absolutely amazing experience. It’s a long day so be ready but it was worth every Euro spent!

Kareem_GDec 4, 2025VIATOR