Montalcino, Pienza & Montepulciano Enogastronomic Grand Tour from Siena

Montalcino, Pienza & Montepulciano Enogastronomic Grand Tour from Siena

Book your Siena wine tour of Montalcino, Pienza, & Montepulciano. Enjoy a day of culture, wine, local food, and tranquil sightseeing of this medieval towns! Read More ...


Key Details


Monday to Sunday

Collection Point

Piazza Gramsci (in front of Bar La Lizza), Siena




Maximun 25 people


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Montalcino, Pienza & Montepulciano Enogastronomic Grand Tour from Siena



Children (7-17)  


Student (ID Required)  


Senior (65+)  


Siena Wine Tour Description

Take a break from museums and galleries and revive your Tuscan vacations with culinary adventures! During our Siena wine tour, you will enjoy authentic Tuscan culture, wine, food in a few of the most enchanting destination in the region. Spend your day immersed in everyday Tuscan life. Our gastronomic tour takes you from Siena to Montalcino where we visit a traditional wine cellar. Naturally, while learning all about the winemaking process, you will sample the wines while snacking on fresh local products. In the afternoon, our wonderful tour leaders will show you around the village and even visit its medieval fortress.

Next, you will head to Pienza and Montepulciano, two towns that represent Val d’Orcia landscapes. Pienza combines architectural beauty with tranquility and is home to the succulent Pecorino cheese. The day trip from Siena ends with a visit to Montepulciano. This town is adorned with Renaissance buildings, churches, and sculptures. All that seamlessly intertwines with a long tradition of its wine, Nobile di Montepulciano, which you will taste in a local winery.

Activity Highlights

Sure, Tuscany is full of incredible works of art, museums, galleries, and palaces. Millions of travelers flood the main Florence and Siena tourist attractions. Yes, they are impressive. But Tuscany has so much more to offer!

Our Siena wine tour of Montalcino, Pienza, and Montepulciano unravels a different face of Tuscany. A face that is natural, artistic, peaceful and ready to awaken all your senses! Yes, there are many wineries in Tuscany but those in Montalcino and Pienza have a long history allowing you to enjoy the velvety wine while enjoying the rustic ambiance of the old towns.

If you are thinking of taking one or two tours from Siena, this wine tasting adventure with a dash of sightseeing is an experience to remember. Besides delicious tasting, you have plenty of free time in each village or town to wander and explore. But no worries, our expert escorts will never be too far should you need their assistance!

History Sneak Peek

All of the three cities you will visit during your day trip from Siena have turbulent histories full of mystery. The past events marked their architecture as well as culture.

For instance, behind the foundation of Montalcino is a group of refugees from the nearby town of Roselle. Despite changing allegiances and rulers, the town kept its medieval urban structure until the present day.

On the other hand, the town Pienza, or at least by its name, is relatively young. The town does stand on an ancient development, Corsignano, of Etruscan or Roman origin. However, Pienza, as we know it today, was established by Pope Pius II in the honor of a great humanist, Enea Silvio Piccolomini who was born here at the beginning of the 15th century.

When it comes to Montepulciano, the legend has it, the Etruscan King Porsenna founded the town in the 6th century BC. Thanks to its strategic location, great farming land and even better winemaking climate the town did well for itself. Although the town experienced its most prosperous period when served as episcopate for the Medici family and the Grand Duke of Tuscany!

So, feeling tempted to treat yourself to a tranquil exploration and indulgent wine and food tasting? Book our Siena wine tour of Montalcino, Pienza, and Montepulciano today! Your taste buds will thank you!

Before You Go

  • Prices for Children from 0-2 years old: free of charge
  • Check-in closes 15 min before departure
  • You must be able to climb and descend stairs
  • Pick up and Drop off on request; price depends on location of your accommodation
  • Private tour is not available at the moment
  • Optional: Pick-up and drop-off from/to accommodation from/to meeting point: €20,00 per person (infants 0-2 free)
  • FR, POR, RUS require a minimum of 4 participants

What is included

  • Travel by GT coach or minivan with air conditioning
  • Expert multilingual escorts
  • Brunello di Montalcino wine tasting
  • Nobile di Montepulciano wine tasting
  • Self-guided visit of Montalcino, Montepulciano, and Pienza
  • Travel insurance and other emergencies
  • Hotel pick-up and drop off
  • Transportation
  • Food, liquors, beers and bottled beverages



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