Take an inside tour visiting enchanting medieval castles where you can experience a unique and personal tour from the towers to the wine cellars. Discover how people lived their life 600 years ago and more. Sample a variety of wines,olive oil, and other product produced by the family that now live in this magnificent buildings. The tour will start at 9.30 am and will include a visit to two castles with wine and olive oil tasting, lunch in a Tuscan farmhouse sampling a variety of traditional dishes with some good Chianti Classico. After lunch we will take a stroll in a medieval walled village where spectacular views can be seen over the Chianti countryside. All our tours are private and run rain or shine. Your itinerary 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

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
The tour will end at about 16.30


“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
“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
“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
“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
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
“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 made it feel as if we were visiting a friend in Tuscany…”
Rene & Anthony, New York, USA
“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