Spend the morning in this intriguing medieval city visiting the most important historical sites.

Accompanied by our historian, Elena , you won’t get a lecture or a boring art-history lesson. Instead you’ll hear the stories and ideals that inspired the Sienese to build their beautiful city to receive the respect and admiration from the European world of the Middle-Ages. You will be privy to the lives of Sienese citizens and their local artists from first-hand documentation and commentary.

– Explore Siena, the Italian town with the largest and most important medieval heritage, in the best way possible: simply by walking along its narrow, winding streets and visiting its most treasured landmarks. Once entering the Duomo and the Palazzo Comunale, you will be transported back to the what the city was during the Middle-Ages.

– The Palio is unlike any other medieval festival throughout all of Europe and Italy. As a true Sienese and an active member of one of the Contradas (the 17 neighborhoods that participate to the race) Your Guide, Elena, will introduce you to the rituals and traditions Sienese inhabitants still embrace with a private visit of one of the Contrada’s Museums

– Along the way, Elena will give you tips on where locals gather, eat, and shop as well as where to find authentic souvenirs.

Take aperitivo Tuscan style in one of the most stunning piazzas in Italy, the impressive Piazza Del Campo where the famous Palio horserace takes place every year. Aperitivo is followed by a three course lunch accompanied by Sienese-Chianti wine. After lunch we head directly for the Chianti Classico. We spend the afternoon “under a Tuscan sun”, surrounded by vineyards, tasting wine and soaking up the atmosphere.

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


“Thankyou again for a wonderful experience… it was a perfect day…”
Rebecca & Ed, California, USA
“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
“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
“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
“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
“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
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