Cortona Itinerary 10 Days: A Journey Through Tuscan Charm (2026)

Arrive in the enchanting hilltop town of Cortona and check into your accommodation. Spend your first day immersing yourself in the timeless atmosphere of the historic center. Begin your exploration at the Piazza della Repubblica, the heart of Cortona, where you can admire the medieval Palazzo del Capitano and the 13th-century Palazzo Comunale. Take a leisurely stroll along the Via Nazionale, the town's main street, lined with charming shops, cafes, and art galleries. As you wander through the labyrinthine streets, you'll discover picturesque corners, ancient stone buildings, and breathtaking views of the Val di Chiana. In the afternoon, visit the Church of San Francesco, a beautiful example of Gothic architecture that houses a relic of the Holy Cross. Then, make your way to the Girifalco Fortress, perched at the highest point of the town. The fortress offers panoramic views of the surrounding countryside and is a great spot to watch the sunset. For dinner, indulge in a traditional Tuscan meal at one of the many excellent restaurants in the historic center. We recommend Trattoria La Grotta, known for its authentic local dishes and cozy atmosphere.

Today is dedicated to exploring Cortona's rich history and artistic heritage. Start your day at the MAEC (Museo dell'Accademia Etrusca e della Città di Cortona), one of the most important Etruscan museums in Italy. The museum is housed in the 13th-century Palazzo Casali and showcases a vast collection of Etruscan, Roman, and Egyptian artifacts. Don't miss the famous Etruscan bronze lampadario, a masterpiece of Etruscan craftsmanship. After immersing yourself in Etruscan history, visit the Diocesan Museum, located next to the Cathedral of Santa Maria Assunta. The museum houses a remarkable collection of religious art, including works by Fra Angelico, Luca Signorelli, and other Renaissance masters. The highlight of the collection is Fra Angelico's Annunciation, a masterpiece of early Renaissance painting. In the afternoon, take a short walk outside the town walls to visit the Eremo Le Celle, a Franciscan hermitage founded by St. Francis of Assisi in the 13th century. The hermitage is a peaceful and spiritual place, with a small church, a chapel, and the cell where St. Francis is said to have stayed. For dinner, try Osteria del Teatro, a charming restaurant with a creative menu and an extensive wine list.

Embark on a scenic day trip to the heart of the Val d'Orcia, a UNESCO World Heritage site known for its rolling hills, cypress trees, and picturesque towns. Your first stop is Montepulciano, a charming hilltop town famous for its Vino Nobile, a prestigious red wine. Stroll through the town's elegant streets, visit the Piazza Grande, and admire the beautiful Renaissance palaces. Don't miss the chance to visit a historic winery for a wine tasting and to learn about the production of Vino Nobile. In the afternoon, continue your journey to Pienza, the "ideal city of the Renaissance." Designed by Pope Pius II, Pienza is a masterpiece of urban planning and architecture. Visit the Piazza Pio II, the heart of the town, and admire the beautiful Cathedral and the Palazzo Piccolomini. Pienza is also famous for its pecorino cheese, so be sure to visit a local cheese shop for a tasting. Before heading back to Cortona, take some time to enjoy the breathtaking views of the Val d'Orcia from the town's panoramic terraces. For dinner back in Cortona, we suggest La Bucaccia, a restaurant renowned for its creative take on Tuscan classics.

Take a day trip to the magnificent city of Siena, one of the most beautiful medieval cities in Italy. Start your exploration at the Piazza del Campo, the heart of Siena and one of the greatest medieval squares in Europe. Admire the unique shell shape of the piazza and the impressive Palazzo Pubblico with its Torre del Mangia. If you're feeling energetic, climb the 400 steps to the top of the tower for breathtaking views of the city and the surrounding countryside. Next, visit the Siena Cathedral (Duomo di Siena), a masterpiece of Italian Gothic architecture. The cathedral's exterior is adorned with intricate carvings and statues, while the interior is a treasure trove of art, including works by Michelangelo, Donatello, and Bernini. Don't miss the Piccolomini Library, with its stunning frescoes by Pinturicchio. In the afternoon, wander through Siena's charming medieval streets, discover hidden courtyards, and browse the local shops. For a sweet treat, try panforte, a traditional Sienese fruitcake. Before heading back to Cortona, enjoy an aperitivo in the Piazza del Campo and soak up the vibrant atmosphere of this magical city.

Immerse yourself in the flavors of Tuscany with a hands-on cooking class and wine tasting experience. Several agriturismos and cooking schools in the Cortona countryside offer classes where you can learn to prepare traditional Tuscan dishes using fresh, local ingredients. Under the guidance of a local chef, you'll learn the secrets of making homemade pasta, savory sauces, and delicious desserts. After the class, you'll get to enjoy the fruits of your labor with a delicious lunch, paired with local wines. In the afternoon, continue your culinary journey with a visit to a local winery. The area around Cortona is known for its excellent wines, including Syrah and Sangiovese. Take a tour of the vineyards and cellars, learn about the winemaking process, and indulge in a tasting of the estate's wines. This is a great opportunity to purchase some wine to take home as a souvenir. For a relaxed evening, enjoy a light dinner at a local enoteca (wine bar) in Cortona, where you can sample a variety of local wines and cheeses.

Embark on a spiritual journey to the beautiful town of Assisi, the birthplace of St. Francis and St. Clare. Located in the neighboring region of Umbria, Assisi is a UNESCO World Heritage site and a major pilgrimage destination. Start your visit at the Basilica of San Francesco, a magnificent two-level church that houses the tomb of St. Francis. Admire the stunning frescoes by Giotto and other medieval masters that depict the life of the saint. After visiting the basilica, explore the charming medieval streets of Assisi. Visit the Piazza del Comune, the town's main square, and admire the Roman Temple of Minerva. Then, make your way to the Basilica of Santa Chiara, which houses the tomb of St. Clare and the famous San Damiano Cross. In the afternoon, take a walk up to the Rocca Maggiore, a medieval fortress that offers panoramic views of Assisi and the surrounding countryside. Before heading back to Cortona, take some time to reflect and enjoy the peaceful atmosphere of this sacred town.

Take a break from sightseeing and spend a relaxing day at Lake Trasimeno, the largest lake in central Italy. Located just a short drive from Cortona, the lake offers a variety of recreational activities and charming lakeside towns to explore. Start your day in Castiglione del Lago, a picturesque town with a medieval fortress and a beautiful lakeside promenade. Take a walk through the town's charming streets, visit the Palazzo della Corgna, and enjoy the views of the lake from the fortress. In the afternoon, take a ferry to Isola Maggiore, the largest of the three islands on the lake. The island is a peaceful and car-free oasis, with a small fishing village, a Romanesque church, and a castle. Take a walk around the island, enjoy the beautiful scenery, and have lunch at one of the lakeside restaurants. You can also go for a swim in the lake or simply relax on one of the beaches. Before heading back to Cortona, enjoy a delicious gelato by the lake and watch the sunset over the water.

Discover the artistic and historical treasures of Arezzo, a beautiful city located just a short train ride from Cortona. Arezzo is famous for its medieval architecture, its rich history, and its connection to the film "Life is Beautiful." Start your visit at the Piazza Grande, one of the most beautiful squares in Tuscany, and admire the unique mix of architectural styles. The piazza is also the setting for the Saracen Joust, a medieval tournament that takes place twice a year. Next, visit the Basilica of San Francesco, which houses the famous fresco cycle "The Legend of the True Cross" by Piero della Francesca, a masterpiece of Renaissance art. Then, make your way to the Arezzo Cathedral, a beautiful Gothic church with stunning stained-glass windows. In the afternoon, explore the Roman Amphitheater and the Archaeological Museum. Before heading back to Cortona, take a walk along the Corso Italia, Arezzo's main shopping street, and browse the local shops.

Spend your last full day in Cortona at a leisurely pace. In the morning, browse the local shops for souvenirs and gifts to take home. Cortona is known for its beautiful ceramics, leather goods, and local food products. You'll find a variety of shops along the Via Nazionale and in the smaller side streets. This is a great opportunity to purchase some Pecorino cheese, olive oil, or a bottle of local wine. In the afternoon, relax and enjoy the charming atmosphere of Cortona. You could revisit one of your favorite spots, enjoy a coffee at a sidewalk cafe, or simply sit on a bench and people-watch in the Piazza della Repubblica. For your farewell dinner, treat yourself to a special meal at one of Cortona's top restaurants. We recommend Ristorante Tonino, which offers a refined dining experience with a modern twist on Tuscan cuisine. Raise a glass of prosecco and toast to an unforgettable 10-day journey through the heart of Tuscany.

Enjoy a final Tuscan breakfast and take one last stroll through the charming streets of Cortona. Depending on your flight schedule, you may have some time for some last-minute souvenir shopping or to visit a spot you missed. When it's time to leave, check out of your accommodation and head to the airport for your departure. We hope you had a wonderful time exploring Cortona and the beautiful region of Tuscany. Arrivederci!