Arezzo and Cortona
Discover the ancient Etruscan heritage and storybook hilltop charm of eastern Tuscany on an exclusive private day trip from Florence, pairing the Gothic artistry of Arezzo with the romantic stone lanes of Cortona.
The Tour
Leave Florence behind for a scenic journey into the rolling, sun-drenched landscapes of eastern Tuscany, exploring a captivating side of the region steeped in deep antiquity, cinematic charm, and authentic local life. Your private English-speaking driver greets you directly at your hotel lobby in Florence in a premium luxury vehicle, escorting you smoothly through the picturesque Arno Valley toward the historic hill city of Arezzo.
Once a dominant capital of the ancient Etruscan Dodecapolis and later a flourishing medieval commune, Arezzo is celebrated for its extraordinary archaeological legacy and layered architectural beauty. Your morning begins with a stroll through the town’s quiet noble quarters and atmospheric stone lanes. Ascend to the city’s crown to admire the monumental Gothic Cathedral, dominating the hilltop with its soaring interior and magnificent stained-glass windows. From there, wander down to the iconic Piazza Grande, renowned for its dramatic sloping pavement, medieval tower-houses, and elegant Renaissance loggias designed by Giorgio Vasari—a cinematic setting immortalized in Roberto Benigni’s Oscar-winning film, La Vita è Bella (Life is Beautiful).
Continuing your journey through the picturesque countryside, ascend to the ancient walled town of Cortona, perched dramatically high above the fertile Val di Chiana. As one of the oldest settlements in central Italy, Cortona radiates timeless charm with its steep cobblestone alleys, artisan ceramic workshops, and panoramic vistas. Spend a leisurely afternoon exploring its lively civic heart in Piazza della Repubblica, visiting the town's historic churches, and browsing local enotecas. Here, you will have ample time to pause for a relaxed lunch at an authentic hillside trattoria, savoring handmade pici pasta, regional delicacies, and local vintages while soaking in the warmth of the Tuscan sun. After a deeply rewarding day of ancient history and hilltop romance, sit back and unwind on a smooth, comfortable drive back to your hotel in Florence.
Once a dominant capital of the ancient Etruscan Dodecapolis and later a flourishing medieval commune, Arezzo is celebrated for its extraordinary archaeological legacy and layered architectural beauty. Your morning begins with a stroll through the town’s quiet noble quarters and atmospheric stone lanes. Ascend to the city’s crown to admire the monumental Gothic Cathedral, dominating the hilltop with its soaring interior and magnificent stained-glass windows. From there, wander down to the iconic Piazza Grande, renowned for its dramatic sloping pavement, medieval tower-houses, and elegant Renaissance loggias designed by Giorgio Vasari—a cinematic setting immortalized in Roberto Benigni’s Oscar-winning film, La Vita è Bella (Life is Beautiful).
Continuing your journey through the picturesque countryside, ascend to the ancient walled town of Cortona, perched dramatically high above the fertile Val di Chiana. As one of the oldest settlements in central Italy, Cortona radiates timeless charm with its steep cobblestone alleys, artisan ceramic workshops, and panoramic vistas. Spend a leisurely afternoon exploring its lively civic heart in Piazza della Repubblica, visiting the town's historic churches, and browsing local enotecas. Here, you will have ample time to pause for a relaxed lunch at an authentic hillside trattoria, savoring handmade pici pasta, regional delicacies, and local vintages while soaking in the warmth of the Tuscan sun. After a deeply rewarding day of ancient history and hilltop romance, sit back and unwind on a smooth, comfortable drive back to your hotel in Florence.
Duration
8 hours
Flexibility
Itinerary and pace managed directly with your private driver
Services include pickup from and drop-off back at either your hotel or at your cruise ship in one of our luxury vehicles by an English-speaking driver.
Lunch, gratuities, and any entrance fees to attractions are not included. Also please note that we may change the order of the itinerary at our discretion.
Multiple booking discounts are available when you book more than one tour or excursion with us. Please note that these discounts do not apply to airport or port transfers.
This tour is suitable for families with children, with a comfortable pace and private service that makes the day easier to enjoy together.
