Tuscany Wine & Hills from Siena - Small Group

From€98.04
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

Itinerary

1

Start your trip at Siena Station Ferrovia, where you will meet the staff. You will recognize them by their green shirt. You will travel by minivan.

Duration: 1h 30mAdmission: NOT_APPLICABLE
2

Explore Montepulciano with free time to enjoy its historic streets and scenic viewpoints. Enjoy a wine tasting and wine cellar visit. Try the famous Nobile di Montepulciano wine.

Duration: 2 hoursAdmission: NOT_APPLICABLE
3

Enjoy free time in Pienza to explore its charming Renaissance streets, scenic viewpoints, and shops famous for pecorino cheese.

Duration: 2h 30mAdmission: NOT_APPLICABLE
4

Wine tasting and wine cellar visit. Admire the stunning Val D'Orcia with its incredible landscape full of olive groves, vineyards and cypresses. For its beauty has been declared world cultural heritage from UNESCO.

Duration: 1 hourAdmission: NOT_APPLICABLE
5

Set in the heart of Tuscany, Montalcino is a charming hilltop town renowned for its world-class wine and authentic atmosphere. Enjoy time to explore its historic streets, browse local shops, and discover regional specialties. Experience the flavors of the area with a wine tasting featuring the famous Brunello di Montalcino, paired with traditional local snacks. A perfect stop to relax, taste, and immerse yourself in Tuscan culture.

Duration: 2h 15mAdmission: NOT_APPLICABLE
6

Return to Siena

Duration: 1h 30mAdmission: NOT_APPLICABLE

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

Traveler reviews

4.0
105 reviews
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10

Great day trip!

Allegra ( our guide) and Silvio ( our driver) were both amazing! Allegra gave lots of useful information and was very knowledgeable about the history of the area! She kept us all to schedule without pressuring us, and made the whole trip an excellent experience!! Thanks to both, we had an amazing time!!

Maria_FJun 20, 2026VIATOR

Wonderful tour in Val d’Orcia

My wife and I took the tour and we loved it. Regarding the service, I must say it was first-class: punctual, attentive, helpful, and fun. About the tour… it was wonderful. The food was first-class, the timing for visiting the places was very good, and the wine tasting was incredible. Sofia (the guide) and Alberto (the driver) were excellent.

L3536HTmiguelgJun 9, 2026TRIPADVISOR

A wonderful Tuscany experience with Sofia and Marco

We had a wonderful day exploring Tuscany on this tour. The landscapes were beautiful, the experience was very well organized, and we really enjoyed visiting the places where the wines rest and mature. The wine tastings were excellent and gave us a great appreciation for the region and its traditions. A special thank you to Sofia, who was very kind, welcoming and attentive throughout the whole day. She made the experience feel personal, relaxed and well organized, always making sure everyone was comfortable and enjoying the tour. We would also like to thank Marco, our driver, who was professional, friendly and drove very safely through the Tuscan roads. His calm and careful driving made the whole day much more comfortable and stress-free. The lunch stop was also a highlight. We had a Tuscan pasta with an excellent ragù that was honestly one of the best pastas we have ever had in our lives. Overall, it was a beautiful and memorable experience in Tuscany. We highly recommend this tour to anyone visiting Siena and wanting to enjoy the Val d'Orcia, taste great wines and have a very well organized day.

JuniomaJun 2, 2026TRIPADVISOR

Wonderful day in Val d'Orcia

A wonderful day in the breathtaking Val d'Orcia with our really friendly and knowledgeable guide, Sofia, and great driver, Marco. We loved the stops at Montepulciano, Pienza and Montalcino. So picturesque. A good amount of time at all locations. Lunch was fabulous inside the rustic restaurant of the winery. And beautiful scenery for the second wine tasting of Brunello. Our original tour couldn't run but 'My Tour in Italy' were so helpful in providing us an alternative excursion - thank you also to Pamela who arranged this for us!

AM402Jun 2, 2026TRIPADVISOR

Great tour

This was a great tour. Great stops. Great vino. Great tour guide. Emma was attentive, helpful and informative. She went out of her way to make every single one of us feel special. I could not have asked for a better person

Allen KMay 19, 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.