Tuscany Wine & Hills from Siena - Small Group

From€129
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

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101 reviews
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10

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

Under the Tuscan Sun

A lovely day exploring 2 beautiful Tuscan towns and 2 excellent wine tasting experiences. Alessandra was a terrific tour guide. The small bus was very comfortable. A perfect way to see the countryside without the stress of driving and parking.

739pattywOct 8, 2025TRIPADVISOR

Scenic drive

Our guide Luca was very informative. The first winery we visited did not give us the attention we deserved. They took in another group and paid more attention to them. They left us with little time to visit the area. I would have liked to have 3 different tastings. Felt more like a senic drive.

Marlisa_COct 5, 2025VIATOR

Valeska was a good guide on this tour.

Although I quite enjoyed this tour, it wasn't the one I chose. I had hoped to do the small group tour to Pienza and Montepulciano. This was cancelled and I was offered the winery tour to Sangimignano and Montacito.

Relax101830Sep 24, 2025TRIPADVISOR

We had a very...

We had a very knowledgeable tour guide and great driver. The wine tours were great as well as the two cities that we visited.

Benjamin_MMar 15, 2025VIATOR

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.