Arezzo Itinerary 5 Days: A Journey Through Tuscan Charm (2026)

Arrive in Arezzo and check into your accommodation. Begin your exploration in the heart of the city at the Piazza Grande, a stunning medieval square that is the backdrop for the annual Joust of the Saracen. Admire the eclectic mix of architectural styles, from the Romanesque apse of the Pieve di Santa Maria to the Renaissance Logge Vasari. Take a moment to soak in the atmosphere at one of the many cafes lining the square. In the afternoon, delve into the city's artistic heritage at the Basilica di San Francesco, home to Piero della Francesca's magnificent fresco cycle, the Legend of the True Cross. This masterpiece of the Renaissance is a must-see for any art lover. For dinner, indulge in authentic Tuscan cuisine at Trattoria La Lancia d'Oro, known for its traditional dishes and charming ambiance.

Today, we explore the upper part of the city, starting with the Arezzo Cathedral (Cattedrale di San Donato). This impressive Gothic cathedral houses a stunning stained-glass window by Guillaume de Marcillat and a fresco of Mary Magdalene by Piero della Francesca. From there, make your way to the Medici Fortress, a 16th-century fortress that offers panoramic views of the city and the surrounding countryside. Take a walk along the ramparts and enjoy the breathtaking scenery. In the afternoon, visit the Casa Vasari, the former home of the famous Renaissance artist and architect Giorgio Vasari. The house is now a museum showcasing his life and work. Afterwards, explore the nearby Roman Amphitheater, a reminder of Arezzo's ancient past. For dinner, try Osteria dei Mercanti, a cozy restaurant serving delicious local specialties.

If your visit coincides with the first Sunday of the month, don't miss the Arezzo Antique Fair, one of the most famous antique markets in Italy. Browse through a vast array of antiques, collectibles, and curiosities, and perhaps find a unique souvenir to take home. If it's not an antique fair day, spend the morning exploring the city's many artisan shops and boutiques. In the afternoon, immerse yourself in the local culture with a visit to the Mercato delle Logge, a bustling covered market where you can find fresh produce, local cheeses, and other Tuscan delicacies. This is a great place to pick up some ingredients for a picnic or to simply soak in the lively atmosphere. For dinner, enjoy a traditional Tuscan meal at Antica Osteria l'Agania, a historic restaurant that has been serving locals for generations.

Take a day trip to the charming hilltop town of Cortona, made famous by Frances Mayes' book, "Under the Tuscan Sun." Just a short train or bus ride from Arezzo, Cortona offers stunning views of the Val di Chiana and a labyrinth of narrow medieval streets to explore. Visit the Piazza della Repubblica, the town's main square, and the Museo Diocesano, which houses a collection of religious art. In the afternoon, wander through the town's many artisan shops, art galleries, and cafes. Don't miss the opportunity to visit Bramasole, the villa that inspired "Under the Tuscan Sun." For lunch, enjoy a delicious meal at a trattoria with a view, such as La Loggetta. Return to Arezzo in the evening.

Enjoy a final Tuscan breakfast and take a last stroll through the streets of Arezzo. Depending on your flight schedule, you may have time for some last-minute souvenir shopping or a final visit to your favorite spot in the city. Afterwards, make your way to the airport for your departure, filled with memories of your unforgettable journey through the heart of Tuscany. We hope you have enjoyed your time in Arezzo and that this itinerary has helped you to discover the best of what this beautiful city has to offer. Arrivederci!