Tuscany Wine & Hills from Siena - Small Group

From€109.65
10 hours
Siena, Italy

About this activity

Experience Tuscany's finest wines and picturesque landscapes on a guided tour from Siena, visiting Montalcino, Pienza, and Montepulciano.

Highlights

  • Explore Montalcino's historic center
  • Taste renowned Brunello di Montalcino wine
  • Discover Pienza's Renaissance architecture
  • Sample Pecorino cheese in Pienza
  • Stroll through Montepulciano's medieval streets

Full description

Indulge in the rich flavors and stunning vistas of Tuscany on this small-group tour from Siena. Visit the historic town of Montalcino, renowned for its Brunello di Montalcino wine, and enjoy a guided wine tasting at a local winery. Explore Pienza, a UNESCO World Heritage site celebrated for its Renaissance architecture and delicious Pecorino cheese. Wander through the charming streets of Montepulciano, famous for its Vino Nobile di Montepulciano. This tour offers a perfect blend of culture, history, and gastronomy, providing an unforgettable Tuscan experience.

Included / Excluded

  • Visit to Montalcino, Pienza, and Montepulciano
  • Wine tasting at local wineries
  • Transportation in a comfortable minivan
  • Lunch and personal expenses

Meeting point

Start Location

Unknown location

Important information

Know before you book

  • Minimum booking of 2 people required
  • Tour operates rain or shine; dress appropriately for the weather
  • Please inform the operator of any dietary restrictions in advance

Know before you go

  • Wear comfortable walking shoes for exploring the towns
  • Bring a camera to capture the scenic landscapes
  • Carry a bottle of water to stay hydrated

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

  • Stroller Accessible
  • Easy Public Transport
  • Infants Required On Laps
  • Infant Seats Available

Good to know

  • Please meet our staff outside Siena Railway Station (Stazione di Siena – Ferrovia), in front of the clock tower at the main station entrance.
  • Please note that the Italian options require a minimum of 4 participants. If the minimum is not reached, the tour is guaranteed in English.

Traveler reviews

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Beautiful tour

The tour was beautiful, Alessandra was amazing, she explained everything and was very considerate of the group, we had a wonderful time.

Sharon_GOct 4, 2026VIATOR

Lovely day in Wine Country

Fantastic wine and tour. Marta and Alessio were the best! Highly recommend from an experienced traveler.

pmlalthoffOct 1, 2026TRIPADVISOR

Average/Disappointing

This could hardly be called a wine tour and we did not get what was advertised. We visited three villages and had free time in each. This was nice. The tour advertised a Tuscan lunch, tours if two wineries and 5 wine tastings. The lunch was very good and included two small glasses of wine. As for the wine tours, both times we were told that we can visit the cellar if there was time. There was no guide and no chance to walk in the vineyards etc. When we got to the second winery, the setting in the garden was nice but there were not enough seats, glasses and there were not enough glasses. Another tour joined ours and there was only one person setting up, running to get more glasses and wine. Then proceeded with a 15 minute sales pitch for the wines. We only got an once of two different wines and if we wanted the promised 5th winery, there was an extra $10 euro charge. Oh did I mention the glasses were smudged and lipstick stained. All in all it was an average tour at best and mostly disappointing.

joeaW4009UKOct 1, 2026TRIPADVISOR

Great tour!

We had an amazing time on the tour and absolutely loved it! Everything was very enjoyable and well organized. The cities included in the itinerary are beautiful and definitely worth visiting. The whole team was fantastic. Our guide, Sofi, and our driver, Claudio, were both incredibly friendly, attentive, and helpful throughout the entire day. They made sure we had everything we needed and made the experience even more enjoyable. We highly recommend this tour!

_mvlmoraisSep 29, 2026TRIPADVISOR

Fantastic day with Sofia and Claudio in wine country!

Sofia and Claudio were fabulous hosts- making each step of the day seemless, fun, and enjoyable! We had a fabulous day and Sofia kept everyone engaged and happy- always anticipating our next need or question! WhatsApp was a clever way to keep the group informed and on schedule! We met the 27th generation winemaker- what an experience! Thank you Sofia and Claudio!!

Compass15937706028Sep 29, 2026TRIPADVISOR

Additional information

Portuguese/Chinese language: Available on selected days and will be guaranteed with minimum 4 pax, if the minimum is not met the tour will be done in English or Spanish.