Arezzo Itinerary 7 Days: A Journey Through Tuscan Charm (2026)

Arrive in Arezzo and check into your accommodation. Spend your first day exploring the city's historic heart. Start at the Piazza Grande, the city's main square, known for its unique sloping design and surrounding medieval buildings. Admire the Vasari Loggia, a masterpiece of Renaissance architecture, and the impressive Palazzo della Fraternita dei Laici. In the afternoon, visit the Basilica of San Francesco, home to Piero della Francesca's stunning fresco cycle, 'The Legend of the True Cross'. This is one of the most important works of the Italian Renaissance and a must-see for any art lover. Afterward, wander through the charming streets of the old town, discovering hidden courtyards, artisan shops, and cozy cafes. For dinner, indulge in some authentic Tuscan cuisine at one of the many traditional osterias in the city center, such as Osteria L'Agania.

Today, explore the upper part of Arezzo. Start your day at the Arezzo Cathedral (Cattedrale di San Donato), a magnificent Gothic church with stunning stained-glass windows and a beautiful terracotta altarpiece by Andrea della Robbia. From the cathedral, walk to the Medici Fortress, a 16th-century fortress offering panoramic views of the city and the surrounding countryside. It's the perfect spot for some great photos. In the afternoon, delve into Arezzo's Roman past at the Roman Amphitheater and the adjacent Archaeological Museum. The museum houses a fascinating collection of Etruscan and Roman artifacts, providing insights into the city's ancient history. In the evening, enjoy an aperitivo at a bar in Piazza Grande, soaking up the lively atmosphere of the square.

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 breathtaking views of the Valdichiana and Lake Trasimeno. Explore the town's steep, narrow streets, browse the artisan shops, and visit the Diocesan Museum, which houses a fine collection of Renaissance art, including works by Fra Angelico. Don't miss the Church of Santa Margherita, located at the top of the town, for its stunning views and beautiful architecture. For lunch, enjoy a delicious meal at one of Cortona's many excellent restaurants, such as La Bucaccia, known for its traditional Tuscan dishes. In the afternoon, you can visit the nearby Franciscan hermitage, Le Celle, a peaceful and spiritual place founded by St. Francis of Assisi.

Dedicate today to exploring the legacy of Giorgio Vasari, one of Arezzo's most famous sons. Visit the Casa Vasari, his former home, now a museum showcasing his life and work. Admire the beautifully frescoed rooms and learn about his contributions to art and architecture. Afterward, visit the Church of Santa Maria della Pieve, a stunning example of Romanesque architecture with a unique bell tower known as the 'tower of a hundred holes'. If your visit coincides with the first weekend of the month, don't miss the Arezzo Antiques Fair, one of the largest and most famous in Italy. The Piazza Grande and the surrounding streets are filled with stalls selling a vast array of antiques, from furniture and paintings to jewelry and ceramics. It's a fantastic opportunity to find a unique souvenir and experience the lively atmosphere of the market.

No trip to Tuscany is complete without a wine tasting experience. Today, venture into the Chianti Rufina wine region, located just north of Arezzo. This area is known for producing high-quality Chianti wines. You can book a guided tour or rent a car and explore the scenic countryside at your own pace. Visit a local winery, such as Fattoria di Grignano or Castello del Trebbio, for a tour of the vineyards and cellars, followed by a tasting of their wines. Many wineries also offer lunch, allowing you to savor delicious Tuscan food paired with their wines. Enjoy the beautiful landscapes of rolling hills, vineyards, and olive groves. It's a perfect way to relax and experience the essence of Tuscany. In the evening, return to Arezzo and enjoy a farewell dinner at a restaurant of your choice.

Explore the beautiful Casentino Valley, a pristine and spiritual area north of Arezzo. Your main destination is the medieval town of Poppi, dominated by the impressive Castello dei Conti Guidi. This well-preserved castle offers a glimpse into medieval life and provides stunning views of the valley. Explore the castle's library, chapel, and courtyard. After visiting Poppi, you can explore other charming towns in the Casentino Valley, such as Bibbiena and Stia. The valley is also home to the Camaldoli Monastery and the La Verna Sanctuary, two important spiritual sites founded by St. Romuald and St. Francis of Assisi, respectively. The Casentino Forests National Park offers numerous hiking trails for nature lovers. Enjoy a picnic lunch amidst the beautiful scenery or dine at a traditional restaurant in one of the valley's towns.

Enjoy a final Tuscan breakfast and do some last-minute souvenir shopping. Depending on your flight schedule, you might have time for a final stroll through the historic center, revisiting your favorite spots. Afterward, head to the Arezzo train station or the airport for your departure, taking with you unforgettable memories of your week in Arezzo and Tuscany.