Arezzo Itinerary 10 Days: A Journey Through Tuscan History and Art (2026)

Arrive in Arezzo and settle into your accommodation. Begin your journey in the heart of the city at the Piazza Grande, the most famous and visually striking square in Arezzo. Uniquely slanted and surrounded by a mix of medieval towers and Renaissance loggias, this piazza is the backdrop for the monthly Antiques Fair and the Saracen Joust. Take your time to admire the architecture, including the impressive Palazzo della Fraternita dei Laici with its astronomical clock and the beautiful apse of the Santa Maria della Pieve church. For your first evening, wander through the Corso Italia, the city's main shopping street, lined with elegant shops and historic buildings. As dusk falls, find a cozy spot for an aperitivo and watch the city life unfold. For dinner, indulge in authentic Tuscan flavors at a traditional restaurant like Antica Osteria l'Agania, known for its classic Aretine dishes. This gentle introduction allows you to soak in the atmosphere of this ancient city, setting the stage for the deeper explorations to come.

Today is dedicated to Arezzo's most significant artistic treasure: Piero della Francesca's fresco cycle, 'The Legend of the True Cross.' Located in the Bacci Chapel of the Basilica di San Francesco, this Renaissance masterpiece is a must-see. Book your tickets in advance to secure a viewing slot, as entry is limited. Spend time absorbing the narrative and the revolutionary use of light and perspective that defines Piero's work. The basilica itself, a 14th-century Franciscan church, is a simple yet powerful space that directs all attention to the art within. Afterward, make your way up the hill to the Arezzo Cathedral, dedicated to San Donato. This Gothic cathedral boasts impressive stained-glass windows by Guillaume de Marcillat and a beautiful terracotta altarpiece by Andrea della Robbia. Don't miss the small fresco of Mary Magdalene by Piero della Francesca near the sacristy. Climb the nearby bell tower for a panoramic view of the city and the surrounding countryside. For lunch, try La Buca di San Francesco, a historic restaurant located in the basement of a 14th-century palazzo, offering a menu steeped in local tradition.

Explore Arezzo's ancient Roman past and its strategic military history. Start your day at the Roman Amphitheater, located just outside the main city walls. Though only parts of the original structure remain, it gives a sense of the scale of Roman Aretium. Adjacent to the ruins is the Gaio Cilnio Mecenate Archeological Museum, which houses an impressive collection of Etruscan and Roman artifacts, including the famous Aretine ware pottery. This provides a fascinating glimpse into the city's importance long before the medieval era. In the afternoon, head to the highest point of the city to visit the Fortezza Medicea, a formidable fortress built by the Medici family in the 16th century. The star-shaped fortress offers a commanding view of Arezzo, the Arno valley, and the surrounding hills. It's a perfect place for a leisurely walk along the ramparts and a picnic in the public park that now occupies its grounds. The fortress is a testament to the military architecture of the Renaissance and a symbol of Florentine dominance over Arezzo. End the day with a relaxed dinner at Le Chiavi d'Oro, enjoying modern Tuscan cuisine with a view of the Piazza San Francesco.

Delve into the life and work of another of Arezzo's famous sons, Giorgio Vasari – the painter, architect, and art historian. Begin at the Casa Vasari, his former home, which he personally designed and decorated with frescoes. The museum provides an intimate look into the life of a successful Renaissance artist. Afterward, visit the nearby Museo d'Arte Medievale e Moderna, which houses a significant collection of works by Vasari and other artists from the region, spanning from the Middle Ages to the 20th century. In the afternoon, focus on the magnificent Church of Santa Maria della Pieve. This Romanesque church is one of Arezzo's oldest and most beloved landmarks. Its most striking feature is the facade with its tiers of colonnades, each column unique. The bell tower, known as the 'tower of a hundred holes,' is another iconic feature. Inside, the main attraction is the polyptych by Pietro Lorenzetti on the high altar. The church's simple, spiritual interior provides a peaceful contrast to the ornate exterior. For dinner, explore the restaurants around the Piazza Grande, such as the historic Logge Vasari.

Take a short train or bus ride to the beautiful hilltop town of Cortona, made famous by Frances Mayes' book 'Under the Tuscan Sun.' Perched on a steep hill, Cortona offers breathtaking views over the Valdichiana and Lake Trasimeno. Spend the day exploring its steep, narrow streets, discovering charming artisan shops, and soaking in the timeless atmosphere. Visit the Piazza della Repubblica, the town's main square, and the Palazzo Comunale. Don't miss the Museo dell'Accademia Etrusca e della Città di Cortona (MAEC), which has an extraordinary collection of Etruscan artifacts, including a famous bronze lamp. Also, visit the Diocesan Museum to see Fra Angelico's 'Annunciation.' For a taste of monastic life, walk up to the serene Franciscan hermitage, Le Celle, founded by St. Francis himself, located just outside the town. Enjoy lunch at a trattoria with a panoramic view, such as Osteria del Teatro, before heading back to Arezzo in the late afternoon.

Rent a car or join a tour to explore the Casentino, the beautiful valley north of Arezzo, known for its ancient forests, castles, and spiritual sites. Your first stop is Poppi, a picturesque medieval town dominated by the impressive Castello dei Conti Guidi. This well-preserved castle, often called a prototype for Florence's Palazzo Vecchio, offers a fascinating look into medieval life and stunning views from its tower. Explore the castle's library, chapel, and courtyards. From Poppi, drive into the heart of the Casentino National Park to the Camaldoli Monastery and Hermitage. Founded by Saint Romuald in the 11th century, this spiritual center is divided into two parts: the monastery, with its beautiful church and an old pharmacy selling herbal remedies, and the hermitage, located a few kilometers up the mountain, where monks live in seclusion. The peaceful atmosphere and the ancient forests surrounding the complex make it a perfect place for reflection and a gentle hike. Enjoy a simple, hearty lunch at a restaurant near the monastery before returning to Arezzo.

Today, make a pilgrimage to the Sanctuary of La Verna, one of the most important Franciscan sites in the world. Perched dramatically on a rocky outcrop in the Casentino mountains, this is where St. Francis of Assisi is said to have received the stigmata in 1224. The sanctuary is a sprawling complex of chapels, churches, and cloisters, built on and around the rock. The atmosphere is one of deep spirituality and peace, enhanced by the breathtaking views and the ancient beech and fir forest that surrounds it. Explore the main basilica, the Chapel of the Stigmata (the spiritual heart of the sanctuary), and the Sasso Spicco, a massive rock suspended over a cavern where St. Francis often prayed. The site is still an active monastery, and you may see Franciscan friars going about their daily lives. The natural setting is as powerful as the religious history, with numerous walking paths through the forest. It's a place that invites quiet contemplation, regardless of one's faith. Pack a lunch or eat at the simple restaurant at the sanctuary before making your way back to Arezzo.

Experience the local life of Arezzo by visiting one of its markets. If it's a Saturday, the large weekly market held around the stadium is a bustling affair with everything from fresh produce to clothing and housewares. It's a great place to observe local life and pick up some picnic supplies. On other days, smaller food markets can be found in the city. Immerse yourself in the sights and sounds, and perhaps buy some local cheese, salami, and bread for a simple and delicious lunch. In the afternoon, dive deeper into Tuscan cuisine with a hands-on cooking class. Several schools and private chefs in and around Arezzo offer classes where you can learn to prepare classic regional dishes like homemade pasta, pappa al pomodoro, or cantucci (almond biscuits). This is a wonderful way to connect with the local culture through its food. You'll learn the secrets of Tuscan cooking and enjoy the delicious meal you helped create. It's a fun, interactive, and memorable experience that provides skills you can take back home. In the evening, enjoy the fruits of your labor for dinner.

Spend the day discovering Arezzo's artisan traditions and lesser-known artistic gems. Explore the streets beyond the main tourist trail, looking for small workshops where artisans practice traditional crafts like leatherwork, ceramics, and gold-smithing, a trade for which Arezzo is famous. This is a great opportunity to find unique, high-quality souvenirs and to see craftsmanship that has been passed down through generations. Seek out some of Arezzo's smaller, but no less beautiful, churches. Visit the Church of San Domenico, which houses a painted crucifix by Cimabue, a masterpiece of pre-Renaissance art. Then, find the Church of Santa Maria in Gradi, which has a beautiful terracotta altarpiece by Andrea della Robbia. These quieter spots offer a chance for peaceful contemplation and the discovery of hidden artistic treasures. As the afternoon winds down, find a cafe for a final Italian coffee and pastry. For your farewell dinner, choose a special restaurant like Osteria Grande for a memorable last taste of Aretine cuisine.

On your final morning, enjoy a leisurely breakfast and take one last stroll through the city. Head to the Giardino del Prato, the large park that connects the Cathedral to the Medici Fortress. It's a lovely green space with a large monument to the poet Petrarch, who was born in Arezzo. Find a bench and take a few moments to reflect on your journey through this historic Tuscan city, from the grandeur of its piazze to the quiet spirituality of its churches and the beauty of the surrounding countryside. Depending on your travel schedule, you might have time for some last-minute souvenir shopping or one final, delicious gelato. Pick up any local specialties you want to take home, such as olive oil or wine. Finally, make your way to the train station or pick up your car for your onward journey, filled with memories of the art, history, and flavors of Arezzo.