Cortona Itinerary 5 Days: Under the Tuscan Sun (2026)

Arrive in Cortona and settle into your accommodation. Begin your exploration in the heart of the town at Piazza della Repubblica, the bustling main square. Admire the Palazzo Comunale with its striking clock tower and grand staircase, a perfect spot for people-watching and soaking in the local atmosphere. From here, wander over to the adjacent Piazza Signorelli, home to the impressive Casali Palace and the Teatro Signorelli. These two squares form the social and civic center of Cortona, where locals and visitors alike gather throughout the day. In the afternoon, delve into Cortona's ancient past with a visit to the MAEC (Museo dell'Accademia Etrusca e della Città di Cortona). Housed in the Palazzo Casali, this fascinating museum showcases an extensive collection of Etruscan, Roman, and Egyptian artifacts, including the famous Etruscan Chandelier. Spend a few hours exploring the exhibits to gain a deep appreciation for the region's rich history. For dinner, enjoy a traditional Tuscan meal at Osteria del Teatro, known for its authentic local dishes and charming ambiance. End your evening with a leisurely passeggiata (stroll) through the beautifully lit streets.

Today is dedicated to art and spirituality. Start your morning with a visit to the Museo Diocesano, a small but significant museum that houses a remarkable collection of Renaissance art. The highlight is the stunning "Annunciation" by Fra Angelico, a masterpiece of early Renaissance painting. The museum also contains other works by local artists, providing a glimpse into the artistic heritage of Cortona. After the museum, begin your ascent towards the top of the town, a rewarding walk that offers increasingly spectacular views. Continue your climb to the Basilica di Santa Margherita, a beautiful church dedicated to Cortona's patron saint. From the basilica, it's a short but steep walk further up to the Girifalco Fortress. This Medici fortress offers the most breathtaking panoramic views of Cortona, the Valdichiana, and Lake Trasimeno. In the afternoon, take a short taxi or bus ride to the Eremo Le Celle, a serene Franciscan monastery founded by St. Francis of Assisi in the 13th century. Nestled in a peaceful wooded ravine, this is a place of profound tranquility and spiritual reflection. Explore the simple cells where the friars lived and the beautiful grounds before returning to Cortona for the evening.

No trip to Cortona is complete without paying homage to "Under the Tuscan Sun". Start your day with a walk to the famous Villa Bramasole, the house that Frances Mayes renovated, which inspired her bestselling book and the subsequent film. While the villa itself is a private residence and not open to the public, the walk to get there is beautiful, offering lovely views of the countryside. It's a quintessential Cortona experience that connects you to the story that made this town so famous. Take your time and enjoy the scenic walk, imagining the life described in the book. In the afternoon, it's time to explore the region's renowned wineries. The area around Cortona is known for its Syrah wines, a varietal that thrives in the local terroir. We recommend visiting the Baldetti Winery or the Tenimenti d'Alessandro for a guided tour and tasting. Learn about the winemaking process from grape to bottle and sample a selection of their finest wines, often paired with local cheeses and cured meats. This is a perfect way to immerse yourself in the flavors of Tuscany and enjoy the hospitality of the local producers. Return to Cortona for a relaxed evening, perhaps enjoying a glass of your newly discovered favorite wine.

Today, venture into the stunning Val d'Orcia, a UNESCO World Heritage site celebrated for its picturesque landscapes and charming towns. Take a day trip to Montepulciano and Pienza, two jewels of this region. Start in Montepulciano, a medieval and Renaissance hill town famous for its Vino Nobile. Walk along the main street, the Corso, lined with elegant palaces and churches. Visit one of the historic underground cellars, like Cantina de' Ricci, for a tasting of the noble red wine. Don't miss the Piazza Grande, the town's main square, which features the Duomo and the Palazzo Comunale, offering views reminiscent of Florence's Palazzo Vecchio. In the afternoon, drive to the nearby town of Pienza, the "ideal city of the Renaissance". Designed by Pope Pius II, Pienza is a masterpiece of urban planning and is famous for its Pecorino cheese. Stroll through the charming streets, enjoy the stunning views over the Val d'Orcia from the city walls, and be sure to sample the various types of Pecorino di Pienza at a local shop. The town's main square, Piazza Pio II, is a harmonious ensemble of Renaissance architecture, including the Cattedrale dell'Assunta and the Palazzo Piccolomini. This day trip offers a perfect blend of history, culture, and gastronomy, showcasing the best of the Tuscan countryside.

On your final day, immerse yourself in local life by visiting Cortona's weekly market, held on Saturday mornings. The market fills the streets around Piazza Signorelli with stalls selling everything from fresh produce, cheeses, and meats to clothing, housewares, and local crafts. It's a vibrant and bustling scene, offering a wonderful opportunity to interact with locals and purchase some authentic Tuscan products to take home. Enjoy browsing the stalls, sampling local delicacies, and soaking up the lively atmosphere. This is the perfect place to find unique souvenirs and gifts. After the market, enjoy a final cappuccino at a café in the piazza and take one last stroll through the charming streets of Cortona, perhaps revisiting a favorite spot or discovering a new hidden corner. Depending on your travel schedule, you might have time for a final delicious lunch at a trattoria like La Grotta. Reflect on your wonderful journey through this enchanting part of Tuscany before heading to the airport or your next destination, filled with lasting memories of your time in Cortona. Arrivederci!