Cortona and Arezzo Tour: Under the Tuscan Sun and Medieval Magic

Cortona, nestled within the province of Arezzo, is an enchanting hilltop town beautifully perched high above the vast Val di Chiana plain. It is world-famous as the cinematic backdrop for iconic films, including Roberto Benigni’s masterpiece “Life is Beautiful” and as the primary setting for the 2003 hit “Under the Tuscan Sun” starring Diane Lane.

Beyond its silver-screen fame, this ancient settlement boasts a profound heritage as one of the twelve original Etruscan cities. Its strategic importance continued throughout Roman times, and today, visitors can still admire original sections of the Etruscan city walls which serve as the historic foundation for the present-day fortifications surrounding the town.

Cortona’s Major Attractions

• Basilica of Saint Margaret – Enduring Catholic church with an opulent interior, a 17th-century bell tower & countryside views.
• Villa Bramasole – Charming, hillside property, best-known as the setting of the 2003 film “Under the Tuscan Sun“.
• Porta Sant’Agostino – A historic gate leading directly into the medieval heart of the village.
• Parterre – A public park with manicured gardens offering sweeping views of the Tuscan countryside.
• The Cathedral – A majestic landmark with a rich history dating back to the 11th century.

These are just a few of the many attractions this amazing town has to offer. With its rich history, beautiful architecture, and charming atmosphere, this amazing town is a great place to spend a day immersed in Tuscan beauty and landscape.

Arezzo

Just a short drive away, the city of Arezzo offers a journey into the soul of authentic Tuscany. Most famous as the primary filming location for Oscar-winning cinema, it is a place of profound artistic heritage. Our curated excursion explores the sloping Piazza Grande, one of the most picturesque and unique squares in Italy, surrounded by medieval palaces and the elegant Vasari Loggiato.

Art lovers will be captivated by the Basilica of San Francesco, which houses the legendary “Legend of the True Cross” fresco cycle by Piero della Francesca, a definitive masterpiece of the Early Renaissance. As we wander through the antique-filled streets, you will discover the birthplace of Giorgio Vasari and the towering Cathedral of San Donato. Whether you are hunting for treasures at the famous Antiques Fair or admiring the Romanesque architecture, this destination provides a sophisticated atmosphere that perfectly balances the charm of our private itinerary.

The Major Attractions

• Piazza Grande – A lively medieval square on a slope, lined by 1500s stone buildings housing cafes & antique shops.
• Arezzo Cathedral – Hilltop medieval cathedral featuring a Piero della Francesca fresco & noted stained-glass windows.
• Basilica di San Francesco – This simple 13th-century Roman Catholic church houses the Legends of the True Cross frescoes.
• Fortezza Medicea – A 16th-century fortress with panoramic views of the city.
• Arezzo Città del Natale – A Christmas market that takes place in the Piazza Grande during the holiday season.

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👥 Group Size: Private only — Up to 9 guests
⏱️ Duration: Full day tour from Florence
🗓️ Schedule: Daily at an established hour.
💶 Private Fee: From €680

Expert local guides are available for those already staying in Cortona or Arezzo. We can meet you at your accommodation or a central landmark for a private walking tour; please inquire for the specific fee based on your group size and duration.

If you enjoyed the history of Cortona, you might also like our Siena and San Gimignano tour.

Read what our past guests say about us on TripAdvisor.

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