As a visitor to Tuscany, Cortona – a town in the province of Arezzo – makes a great base because it allows you to experience life in a small town while being close to good link roads. From Cortona you can easily reach the major art cities of Siena and Arezzo (40 minutes) as well as the famous cheese and wine towns Pienza and Montepulciano (which are even closer). There are also two different thermal baths at Chianchiano and Rapolano. Cortona itself has an amazing history of war and being near the border of the Umbria region, it has a different feeling when you walk in the street. There is a great plethora of people that live here. In fact, it is home to many artists and performers. In August the town transforms itself into an open festival where international singers from all over the world make this city burst with beautiful music. Outside the town walls are a breathtaking combination of vineyards, olive trees, sunflowers and tobacco plants which makes the surroundings here unique to other regions in Tuscany. And inside every bottle of wine produced in Cortona there is a world made of men and women that respect the territory and use mostly organic agriculture – even if some of them do not have authentic certification to do so! Arezzo on the other hand is a large city with an ancient history of gold and jewellery making. It also has one of the most incredible antique markets in the region every month, where you can find some great deals – especially if you are a collector. The province itself is home to ‘Chianti Colli Aretini’ and is described as light, soft and not too structured. Not perhaps, great attributes for serious wine connoisseurs, but for the humble wine drinker these are positive characteristics. And one great advantage of this is that Arezzo’s wines have always offered good value for money. 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


“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
“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
“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
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
“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