Soft and dark brown is a good description of Montepulciano’s red wines. The sandy soil makes for soft fruit and texures and the wines age a bit quicker that the Brunello di Montalcino. One advantage of this is that they are more approachable and most of the times better value than Brunello. The confusion comes because Montepulciano is also a red grape variety from the near Abruzzo region this is a different type of grape. The town is 450 meter above sea level and has stunning views over the val D’orcia, from here you can see Cortona. A day in Montepulciano is a journey discovering this delicious wines and get to know a talented wine maker which will show us around his estate. The town itself is beautiful and very well preserved, it has numerous underground cellars and Etruscan tombs. Nearby there is Pienza a renaissance style town built by Pope Pius 2nd which is the center of the Pecorino cheese production. Here you can sample some of the best sheep cheese in the region.

We have imagine several itineraries bringing together highlights of Montalcino and knowledge of the region’s food and wine. All our tours are private and run rain or shine. Each of the itineraries include:

  • Your personal guide, fluent in English
  • Wine tastings
  • Three course lunch and wine
  • Pick up and drop off between hotel and destination
  • Transport in spacious, air conditioned vehicle


I want to thank you for showing us the wonderful, beautiful and picturesque Chianti region. Also touring your hometown and meeting your wife and precious children were such a welcome treat. The wine tasting and the ...
Joan Everett Oklahoma
“We were in Italy for just over a week to see Rome, Florence and Venice… Without a doubt though, this was the highlight of the trip…”
David & Margaret, Edinburgh, Scotland
“Enzo made it feel as if we were visiting a friend in Tuscany…”
Rene & Anthony, New York, USA
“It was so special to be able to go where most people don′t get a chance to see… We will recommend Chianti Inside Out to all who ask…”
Sean, Essex, England
“Enzo was fabulous! We really enjoyed the day you planned for us to spend with him at the winery and cooking class. So much so, that we hired him for the next day to take us ...
Faith, Esher, England
“I wanted to express my deepest appreciation for your making my first trip to Tuscany so spectacular and memorable. It would be hard to imagine a better guide, driver, wine expert, food aficionado, and basically local ...
David, New York, USA
“Thankyou again for a wonderful experience… it was a perfect day…”
Rebecca & Ed, California, USA
“Thanks so much Enzo for the great day in the Chianti countryside… you were the perfect host! Our two weeks in Florence would not have been complete without that day!”
Wayne & Donella, Pennsylvania, USA
“What a perfect way to experience Tuscany up close and personal. We learned about and tasted the best wines and olive oil in Italy with our tour guide Enzo.”
Sandra, California, USA

Tour prices per person per day

Please be aware that these prices depend on the place you stay

    • 2 people = 220€pp
    • 3 people = 210€pp
    • 4 people = 190€pp
    • 5 people = 180€pp
    • 6 people = 170€pp
    • 7 people = 160€pp
    • 8 people = 150€pp