Montalcino, Pienza & Montepulciano Enogastronomic Grand Tour

Montalcino, Pienza & Montepulciano Enogastronomic Grand Tour

Book Montepulciano wine tours today and enjoy a visit to a wine cellar in Pienza, tasting of wine and local produce & tasting Nobile di Montepulciano wine! Read More ...


Key Details


Monday to Sunday

Collection Point

Inside Santa Maria Novella Train Station, Florence - In front of the pharmacy with the green cross




Maximun 25 people


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Easy Cancellation
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Montalcino, Pienza & Montepulciano Enogastronomic Grand Tour



Children (7-17)  


Student (ID Required)  


Senior (65+)  



Enrich your Tuscany vacations with a day full of culture, art, wine, and delicious food. Our Montepulciano wine tours from Florence take you on an unforgettable adventure in the most imposing places in the Tuscan region.

Our Tuscany gastronomic tour begins with a visit to an authentic wine cellar in Montalcino. As you learn more about the winemaking process, you will savor the local wines and fresh Tuscan produce. In the afternoon, one of our great tour leaders will show you around town and its medieval fortress.

The tour continues with a visit to Pienza and Montepulciano, two picturesque towns that form the landscape of Val d’Orcia. Pienza is a perfect embodiment of medieval architectural beauty and is home to the succulent Pecorino cheese. At last, we will head to Montepulciano. It's a town of many Renaissance buildings that have witnessed the evolution of its long winemaking tradition. You will taste the famous Nobile di Montepulciano wine in a local winery.  

Activity Highlights

Tuscany overflows with museums, galleries, incredible works of art, and palaces. Each year, millions of visitors flood the main Florence tourist attractions. However, there is much more to explore in this lush central region.

Our Montepulciano wine tours from Florence introduce you a new aspect of Tuscany; An aspect that is natural and ready to wake up all your senses. While there are numerous wineries in Tuscany, Pienza and Montalcino offer you centuries-long traditions intertwined with history and art. Their velvety wines and the rustic ambiance of the ancient towns combine perfectly.  

If you are considering joining one or two tours from Florence, this wine tasting expedition with a splash of sightseeing is a great choice. Besides the delicious tastings, we will give you a plenty of free time in each of the towns to explore on your own.

History Sneak Peek

All of the three towns we will visit poses turbulent histories that made their mark on the culture and architecture of these settlements.

For example, the foundation of Montalcino is work of a group of refugees from the town of Roselle. Despite the many changes of allegiances, rulers, and political conditions, the town managed to keep its medieval urban structure to this day.

On the other hand, Pienza is relatively young (at least by its name). Although the town stands on an ancient development of Etruscan origins, Corsignano, Pienza came about a bit later. It was founded by Pope Pius II to honor a great humanist, Enea Silvio Piccolomini.

Montepulciano, according to a legend, was founded by an Etruscan King Porsenna in the 6th century BC. Thanks to the town’s strategic location, fertile farming land, and excellent winemaking climate, the town did very well for itself since its humble beginnings.

Book our Montepulciano wine tours from Florence today and enjoy a day full of succulent tastes, smells as well as sightseeing and intriguing histories.

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
  • FR, GR, POR, RUS, IT, CH, JP require a minimum of 4 participants
  • Drop-off: €10.00  per person and infant from 0-2 years old is free of charges

What is included

  • Travel by GT coach or minivan with air conditioning
  • Expert Guide
  • 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



Based on 7 reviews

Value for Money
Overall Experience
Collection Point



This area of Tuscany is so lovely, we have had wonderful wine tasting time!

0 1 0

I absolutely recommend this tour. It's different and a great value for money. We had a great tour guide, too. Plus, it's a comfy way to visit a good amount of the Tuscan region.

0 1 0

This was my absolute favorite from the start to the end. The tour guide was excellent. The wineries were so interesting and the wine tasting, especially in Montalcino, was one of the best wine tours I've ever attended. Highly recommend!

0 1 0

We really enjoyed the day away from the city and the beautiful countryside. We visited a lovely vineyard and had great wine tasting experiences.

0 1 0

The sites and town were exactly what we wanted. The wine tasting was wonderful and we had a lot of free time to explore the surroundings. I would have enjoyed a guided tour of all the town on the list, though, a bit more.

0 1 0

Julia had amazing English and good knowledge of the areas. She was very helpful and friendly and made our trip very enjoyable.

0 1 0

Highly recommend this tour, One of the best tour we had. Our kids want to go there again. Thaks to our guide robert.

0 1 0

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