Day trip

From Siena: Val D'Orcia Wine Tour

Activity provider: My Tour in Italy
Day trip

From Siena: Val D'Orcia Wine Tour

Activity provider: My Tour in Italy
Likely to sell out

From US$ 92.18 per person

Likely to sell out

Taste the food and wines of Tuscany on a 10-hour sightseeing tour of Montalcino, Pienza, and Montepulciano. Depart Siena and cross the Tuscan hills, and visit wineries that produce wines such as Brunello di Montalcino and Nobile di Montepulciano.

About this activity

Free cancellation
Cancel up to 24 hours in advance for a full refund
Reserve now & pay later
Keep your travel plans flexible — book your spot and pay nothing today.
Duration 10 hours
Check availability to see starting times.
Live tour guide
English, Italian, Spanish, Chinese, Portuguese


  • Taste the food and wines of Tuscany at local wineries
  • Sample Brunello di Montalcino wines
  • Drive across the gentle, rolling hills of Tuscany
  • Learn more about the wine making traditions
  • See medieval castles and historic towers on hillsides
Full description

Enjoy a day of culture, wine, and food as you visit some of the most impressive towns and villages in Tuscany. See the picturesque town of Pienza, and taste world-famous wines produced in Montalcino and Montepulciano. 

Meet your guide in Siena and join the rest of the group to start your full-day tour. Depart Siena and transfer to a wine cellar in Montalcino. Cross gently rolling hills full of vineyards, and then sample local wines served with a delicious snack of the local produce.

Continue to Pienza to discover the “Touchstone of Renaissance Urbanism.” Considered an artistic jewel of the landscape of Val d’Orcia, Pienza is a perfect combination of architectural beauty and harmony. 

Most of the lanes bearing impressive names overlook the breathtaking landscape of the Val d’Orcia. Unique smells and flavors are entwined with this natural and artistic heritage. Pienza’s most renowned tradition is pecorino cheese.

End the tour at Montepulciano, where the stateliness of its Renaissance buildings and the refined beauty of the town's churches mix with the ancient tradition of winemaking. Enjoy some free time before your return transfer to Siena by bus.

  • Guide
  • Tasting of typical Tuscan products
  • Transportation by air-conditioned GT coach or minivan
  • Brunello di Montalcino wine tasting
  • Tips
  • Lunch
Not suitable for
  • People with mobility impairments

Select participants and date



Meeting point

Meeting point may vary depending on the option booked.

Important information

Know before you go

  • You will have to climb and descend stairs
Customer reviews

Overall rating

4.1 /5

based on 210 reviews

Review summary

  • Guide
  • Transportation
  • Service
  • Organization

Sort by:

Traveler type:

Star rating:

Was a great tour … excellent guide.. Luciano I think his name was … and bus driver great and careful … enjoyed wine tasting and Pienza was great … thunk abit of “ direction” in Montopulciano would have been great .. eg the deep underground cellars of Taluso are a “ must” visit …

March 30, 2023

Pretty good your, couple things could be better. The winery tour and wine sampling was terrific, very informative, nice selection of wines and education, along with cheese, meat, bread nibbles, which was delicious. There was then a stop and free time in Pienza which was quite nice and plenty of time to get lunch and stroll this charming, curated town. This visit to Montepulciano could have been better, in that we weren’t given any wine or sampling at all from one of the most famous of the Tuscan wine regions. Just let loose to explore without any explanation of where to find the main shopping street, which was not nearby, and I only found it after I paid another 8 euro to take a local red bus tour., and then had no time left to shop. No wines to try unless you found your own. That part was tremendously disappointing in an otherwise good trip. I could have fine without the annoying music on the bus, but otherwise the guide was pretty good and the driver got us there and back on time.

Read more

March 30, 2023

This was a really fun way to explore the Tuscany area! It was so great getting to visit a couple of the beautiful towns, and get great food and drink recommendations from our tour guide, Lucenzo. He was a great guide, sharing lots of interesting information and stories about what we were seeing.

March 30, 2023

Product ID: 60232