Cortona Itinerary 14 Days: Under the Tuscan Sun (2026)

Arrive in Cortona and check into your accommodation. Spend the afternoon getting acquainted with the town's historic center. Wander through the main squares, Piazza della Repubblica and Piazza Signorelli, the heart of Cortona. Admire the medieval architecture of the Palazzo Comunale and the Palazzo del Capitano del Popolo. For dinner, enjoy a traditional Tuscan meal at Osteria del Teatro, a charming restaurant known for its local specialties and romantic ambiance. As the sun begins to set, take a leisurely stroll along the town walls for breathtaking panoramic views of the Valdichiana. The warm glow of the setting sun casting long shadows over the ancient stones is a sight to behold. This is the perfect introduction to the magic of Cortona, a town that seems to exist outside of time. The air is filled with the scent of jasmine and the distant sound of church bells, creating a truly enchanting atmosphere.

Delve into Cortona's rich history with a visit to the MAEC (Museo dell'Accademia Etrusca e della Città di Cortona). This fascinating museum houses an extensive collection of Etruscan, Roman, and Egyptian artifacts, including the famous Etruscan Chandelier. In the afternoon, visit the Diocesan Museum, home to a remarkable collection of Renaissance art, including Fra Angelico's 'Annunciation.' After a morning of history and art, enjoy a leisurely lunch at La Bucaccia, a highly-rated restaurant tucked away in a medieval cellar. In the afternoon, explore the narrow side streets and alleyways of Cortona, discovering hidden courtyards and artisan shops. You'll find everything from handmade ceramics to locally produced leather goods. End your day with a glass of local wine at a cafe in Piazza Garibaldi, enjoying the stunning views of the valley below.

Take a short taxi ride or a scenic walk to Eremo Le Celle, a Franciscan monastery founded by St. Francis of Assisi in the 13th century. This peaceful sanctuary, nestled in the woods above Cortona, offers a glimpse into a life of simplicity and contemplation. In the afternoon, climb to the top of the Girifalco Fortress for panoramic views of Cortona and the surrounding countryside. The fortress, built by the Medici family, is a testament to Cortona's strategic importance throughout history. For dinner, try Trattoria Dardano, a family-run restaurant known for its authentic Tuscan home cooking. The hearty pasta dishes and grilled meats are a local favorite. After dinner, take a passeggiata (evening stroll) through the illuminated streets of Cortona, soaking in the magical atmosphere of the town at night.

Take a day trip to the nearby town of Montepulciano, famous for its Vino Nobile. Explore the historic center, visit the Piazza Grande, and climb the tower of the Palazzo Comunale for stunning views. Enjoy a wine tasting at a local cantina, such as Cantina de' Ricci, and savor a delicious lunch at a traditional trattoria. Montepulciano is another beautiful Tuscan hill town, and its wines are not to be missed. In the afternoon, wander through the charming streets of Montepulciano, browsing the artisan shops and enjoying the relaxed atmosphere. Before heading back to Cortona, be sure to purchase a bottle of Vino Nobile to enjoy later. The drive back to Cortona through the rolling hills of Tuscany is a scenic experience in itself.

Immerse yourself in Tuscan cuisine with a hands-on cooking class. Learn how to prepare traditional dishes using fresh, local ingredients. Many cooking schools in Cortona, such as the one at Agriturismo Il Falconiere, offer classes that include a visit to the local market to select produce. This is a fun and delicious way to experience the local culture. After enjoying the fruits of your labor for lunch, spend the afternoon relaxing or exploring more of Cortona at your own pace. You could revisit a favorite spot, browse the shops for souvenirs, or simply relax at a cafe with a good book. For dinner, enjoy a casual meal at a pizzeria, such as Pizza e Focaccia, and savor a classic Italian pizza.

Take a day trip to Pienza, a UNESCO World Heritage site and the 'ideal city of the Renaissance.' Designed by Pope Pius II, Pienza is a masterpiece of urban planning. Explore the Piazza Pio II, visit the Cattedrale dell'Assunta, and sample the town's famous pecorino cheese. The views of the Val d'Orcia from Pienza are simply breathtaking. In the afternoon, take a scenic drive through the Val d'Orcia, one of the most beautiful landscapes in Tuscany. Stop at the iconic Cappella della Madonna di Vitaleta, a small chapel set amidst rolling hills and cypress trees. This is a photographer's paradise, so be sure to have your camera ready. Enjoy dinner at a restaurant in Pienza before heading back to Cortona.

After a busy week of exploring, take a day to relax and rejuvenate. Treat yourself to a spa day at a local hotel, such as the Cortona Resort & Spa. Enjoy a massage, a facial, or simply relax by the pool. This is the perfect way to recharge your batteries for the second half of your trip. In the afternoon, enjoy a leisurely lunch at a cafe with outdoor seating, soaking in the Tuscan sun. You could also spend the afternoon reading a book in a quiet park or garden. For dinner, indulge in a gourmet meal at Ristorante La Loggetta, a restaurant with a beautiful terrace overlooking Piazza della Repubblica.

Take a day trip to Siena, one of the most beautiful medieval cities in Italy. Explore the Piazza del Campo, the main square where the famous Palio horse race is held. Climb the Torre del Mangia for panoramic views of the city. Visit the Duomo di Siena, a masterpiece of Gothic architecture. Siena is a larger city than Cortona, but it is still very walkable and full of charm. Enjoy lunch at a traditional osteria in Siena, and be sure to try the local specialty, pici pasta. In the afternoon, wander through the narrow streets of the different contrade (districts) of Siena, each with its own unique identity. Before heading back to Cortona, enjoy an aperitivo in the Piazza del Campo, soaking in the lively atmosphere.

Explore the beautiful countryside around Cortona with a hike or a bike ride. There are many trails to choose from, ranging from easy walks to more challenging hikes. You can rent bikes in Cortona and explore the country lanes at your own pace. Pack a picnic lunch and enjoy a meal amidst the olive groves and vineyards. In the afternoon, visit a local winery for a tour and tasting. The area around Cortona is known for its Syrah wines, so be sure to try some. This is a great way to experience the agricultural traditions of Tuscany and to meet the people who produce the region's excellent wines. For dinner, enjoy a rustic meal at an agriturismo, a working farm that offers accommodation and meals.

Take a day trip to Arezzo, a city famous for its art, history, and antiques market. Visit the Basilica di San Francesco, home to Piero della Francesca's magnificent fresco cycle, 'The Legend of the True Cross.' Explore the Piazza Grande, a beautiful medieval square that was featured in the film 'Life is Beautiful.' If you're in Arezzo on the first Sunday of the month, don't miss the famous antiques market. Enjoy lunch at a trattoria in Arezzo, and be sure to try the local pasta, bringoli. In the afternoon, visit the Casa Vasari, the former home of the artist and art historian Giorgio Vasari. The house is decorated with frescoes by Vasari and his pupils. Before heading back to Cortona, take a stroll through the Parco del Prato, a large park with a Medici fortress.

Spend a day at Lake Trasimeno, the largest lake in central Italy. Take a ferry to Isola Maggiore, a charming island with a small fishing village. Explore the island on foot, visit the Romanesque church of San Salvatore, and enjoy a fresh fish lunch at a lakeside restaurant. The lake is a beautiful and peaceful place, and it offers a different perspective on the region. In the afternoon, you can relax on one of the lake's beaches, go for a swim, or rent a boat to explore the lake further. There are also several charming towns around the lake, such as Castiglione del Lago and Passignano sul Trasimeno, that are worth a visit. Enjoy the sunset over the lake before heading back to Cortona.

Spend the day exploring Cortona's art galleries and artisan shops. You'll find a wide variety of art, from traditional paintings to contemporary sculptures. Many artists have studios in Cortona, and you can often meet them and watch them at work. This is a great opportunity to purchase a unique souvenir of your trip. In the afternoon, indulge in some retail therapy. Cortona has a great selection of shops, selling everything from designer clothes to local handicrafts. Be sure to visit the weekly market, held on Saturday mornings, for a lively and colorful experience. For dinner, try a new restaurant, such as Ristorante Ambrosia, which offers a modern take on Tuscan cuisine.

Spend your last full day in Cortona revisiting your favorite spots or exploring any places you may have missed. Take a final stroll through the charming streets, savor a gelato in the piazza, and soak in the magical atmosphere of this enchanting town. This is a good time to buy any last-minute souvenirs or gifts for friends and family back home. In the evening, enjoy a farewell dinner at a special restaurant, such as Il Falconiere, a Michelin-starred restaurant located just outside of Cortona. The restaurant offers stunning views of the valley and serves exquisite Tuscan cuisine. This is the perfect way to celebrate the end of your unforgettable trip to Cortona. After dinner, take one last look at the twinkling lights of the valley from Piazza Garibaldi.

Enjoy a final breakfast in Cortona, savoring the last moments of your Tuscan adventure. Depending on your flight schedule, you may have time for some last-minute souvenir shopping or a final stroll through the town. Head to the airport for your departure, filled with wonderful memories of your time in Cortona.