Private Tour of Arezzo and Cortona

Discover two authentic Tuscan gems with a private tour of Arezzo and Cortona, away from the most crowded tourist circuits.

What you can discover

Each tour is fully customizable: choose from the proposed experiences and build your unique itinerary, tailored to your desires.

CORTONA

Cortona fascinates with its Etruscan spirit, uphill streets, and panoramas embracing the Val di Chiana. An authentic village, rich in art, history, and Tuscan atmosphere.

HERMITAGE OF LE CELLE IN CORTONA

The “Hermitage of Le Celle is a place of peace suspended in greenery, where St. Francis lived in prayer. Among silence, nature, and spirituality, one breathes a” mystical and timeless atmosphere.

PIAZZA GARIBALDI AND RUGAPIANA

Piazza Garibaldi offers a breathtaking view of the Val di Chiana, while Ruga Piana invites you to stroll among historic shops and authentic Tuscan shopping. A perfect blend of panorama and tradition.

CORTONA SYRAH

Villa Bramasole, made famous by the book and film ‘Under the Tuscan Sun’, is an optional and unmissable stop for those who dream of Tuscany through cinema and literature.

AREZZO, CATHEDRAL AND PIAZZA GRANDE

Arezzo fascinates with its ancient elegance, among churches, art, and historic workshops. Piazza Grande, with its irregular shape and period buildings, is the scenic heart of the city, also made famous by the film ‘Life is Beautiful’.

Basilica of San Francesco

In Arezzo, the Basilica of San Francesco houses Piero della Francesca’s masterpiece, the Cycle of the True Cross. A place of great charm, where art and spirituality merge in a timeless atmosphere.

Tour photos

Panorama dalla collina di Cortona con vista sulla Valdichiana

Palazzo della Fraternita dei Laici con torre orologio in Piazza Grande ad Arezzo

Facciata del Duomo di Arezzo con scalinata e visitatori durante un tour culturale in Toscana

Piazza Grande e Duomo di Arezzo con palazzi storici

Eremo delle Celle a Cortona immerso nella natura

Torre civica di Cortona vista attraverso un arco del centro storico

WHY CHOOSE TUSCANY EXCURSIONS

Comfort, authenticity, and freedom: travel in style with local drivers with over 10 years of experience, taste authentic flavors, and enjoy a tailor-made experience built around your desires.

Included services and extra options for your private excursion

What's included in the tour

WHAT'S NOT INCLUDED (UPON REQUEST)

What they say about us

       EXCELLENT  
   Based on 208 reviews 
    
 
 
 
   
 
 
      Posted on Tripadvisor  
   
   Frances N 
 8 September 2026
 
 
 Verified A wonderful day at cinque terre Thank you Alessandro ,so much for a lovely day it was a pleasure to have someone with so much knowledge and history of the area drive and show us around . The pick up and drop off at our hotel in Forte dei Marmi made visiting Cinque Terre so effortless .The scenic routes taken and the driving were superb many thanks Frances & Holly
  
 
     Posted on Tripadvisor  
   
   Curious04373723292 
 15 July 2026
 
 
 Verified 10/10 Tuscan Sunset Dinner Excursion We had an incredible experience in Tuscany curated by Leonardo and Alessandro. While staying in Florence we wanted to get into the Tuscan countryside and enjoy a sunset dinner at a winery. Leonardo and Alessandro were able to customize our timeline to meet our needs. Alessandro drove us an hour outside of Florence to San Gimignano, a quaint medieval town with gorgeous views of the countryside and great shopping. They also arranged for a fantastic sunset meal at Cantinetta dei Logi, the restaurant at Colombaio di Santa Chiara. We all enjoyed this so much (Me, My Husband and our teenage son and daughter). Great views, wonderful service and fantastic food. We returned to Florence after about a 5 hour excursion. It was perfect for us. Alessandro is very knowledgeable of the wine history in the area which made the car ride to and from more enjoyable. Thank you Leonardo and Alessandro!
  
 
     Posted on Tripadvisor  
   
   Riley L 
 10 July 2026
 
 
 Verified Cinque Terre Tour Our experience was amazing. We traveled to Cinque Terre with 13 adults. Our two drivers, Sam and Alessandro, were awesome. They gave us a lot of information throughout the drive. Then when we got there, they were provided an easy route to explore the cities.
  
 
     Posted on Tripadvisor  
   
   Tre L 
 9 July 2026
 
 
 Verified Amazing Cinque Terre Tour from Florence We took the Cinque Terre tour from Florence and it was amazing. They took up from our hotel to the town and helped us to the ferry. We would highly recommend the experience! They were able to accommodate our group of 13 easily!
  
 
     Posted on Tripadvisor  
   
   carrie 
 8 July 2026
 
 
 Verified Unforgettable Tuscan day trip We hired Alessandro for a private Tuscan day trip in late June 2026. The day was amazing, we learned more about Tuscany than we ever imagined, we tasted olive oil and wine, and loved spending time with our tour guide. We chose the company because of the prompt response to our initial solicitation and openness to assist in planning an itinerary. Alessandro promptly replied to all of my emails and offered helpful advice when deciding where to go. We ultimately decided to go south from Florence to Siena with a few stops for tastings and sightseeing along the way. Immediately after picking us up, he took us up to the Piazza Michelangelo for an amazing view of Florence. We then embarked on a delightful, educational, and remarkably comfortable road trip through Tuscany. At Alessandro’s suggestion, we stopped at Monteriggioni, a medieval fortress town. Then onto Siena where we toured its stunning Duomo. Alessandro recommended an olive oil tasting at a small oil producer in Panzano. We then tasted wine at Montecalvi Winery in Greve. Alessandro’s extensive knowledge of the history of Tuscany (and a great many other things), his impeccable English, and charming personality made our Tuscan day trip truly unforgettable.
  
 
     Posted on Tripadvisor  
   
   Barbara J 
 6 July 2026
 
 
 Verified Great Guide Leonardo was a fantastic guide He provided interesting information He has wonderful charisma The trip was very pleasant and comfortable He also made lunch reservations for us at a delicious restaurant Thank you Leonardo and Alex
  
 
     Posted on Google  
   
   Mark King 
 24 June 2026
 
 
 Trustindex verifies that the original source of the review is Google. +1
We had an amazing day with Alessandro!! I’d recommend anyone to go on this amazing tour of Tuscany.
  
 
     Posted on Tripadvisor  
   
   Mark K 
 24 June 2026
 
 
 Verified Amazing day in Tuscany We had an amazing day with Alessandro!! I’d recommend anyone to go on this amazing tour of Tuscany.
  
 
     Posted on Tripadvisor  
   
   Kim K 
 24 June 2026
 
 
 Verified Wonderful day seeing areas in Tuscany Alessandro was a great! We got to see some wonderful areas of Tuscany. We at some of the best food at Fontaleoni Winery! Wonderful experience.
  
 
     Posted on Google  
   
   Sonya Baskerville 
 5 June 2026
 
 
 Trustindex verifies that the original source of the review is Google. Working with Leonardo and Tuscany Excursions was an absolute pleasure! From booking to the end of our 6 hours, we had a seamless and enjoyable time visiting Florence, Lucca, and Pisa, and enjoying the great information about the area that Leonardo shared! We needed more flexibility than the excursions that were offered by the cruise line. Tuscany Excursions provided the flexibility we needed for our visit at a very reasonable cost. I highly recommend them and hope to return and use their service.

Frequently Asked Questions

Is the Tour Suitable for Families with Children?

Yes, the tour is private and customizable for families too. Cortona and Arezzo offer safe spaces and interesting attractions for children as well.

How much Time is Spent in each City?

Generally half a day in Cortona and half in Arezzo, but the itinerary is flexible. We can spend more time in one of the two destinations if you prefer.

Is it Possible to Add a Wine Tasting?

Certainly! Upon request, we can include a visit to a winery with a typical lunch and wine tasting.

How Far are Arezzo and Cortona from Florence?

About 1h30 of travel. The route is very scenic and can be enriched with photo stops along the way.

What Happens in Case of Rain?

The tour takes place even in case of rain. The two cities offer many indoor points of interest, including churches, museums, and historic cafes.

Book your Private Tour of Arezzo and Cortona

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