Discover the Timeless Beauty of Cortona

Cortona (Arezzo)

Cortona, visible from Siena House, is a charming Tuscan town known for its long views and rich cultural heritage. Explore its medieval streets, indulge in local delicacies, and experience the unique blend of history and natural beauty that makes Cortona a beloved destination.

Perched high on the side of the Apennines and visible from Siena House, the charming town of Cortona offers stunning long views, delicious gelato, and one of our favorite spots for a leisurely passeggiata (stroll). Nestled in the heart of Tuscany, Cortona is a must-visit destination for anyone interested in exploring Italy’s rich history and natural beauty.

Surrounded by the rolling hills, woodlands, and vineyards of the Val di Chiana valley, Cortona is an ideal location for outdoor activities and wine tastings. The town’s old alleys, medieval structures, and cultural attractions provide ample opportunities to delve into Tuscan art, cuisine, and traditions.

Key Information:

  • Distance from Hotel: 30 kilometers
  • Time to Drive: 30 minutes
  • Recommended for: History buffs, foodies, wine enthusiasts, outdoor lovers, and shoppers
  • Best Time to Visit: Any time of day; restaurants are typically closed between 1 PM and 4 PM
  • Suggested Duration: A few hours to a full day
  • Itinerary Suggestions: Combine with wine tasting in Chianti, a visit to Arezzo, or a trip to Lake Trasimeno. Also, consider a cross-country drive to The Mall or the Prada factory outlet.

Special Highlights:

  • Santa Margarita Church: Head up, up, up to this beautiful church and enjoy the long views from the Fortezza above it, especially before sunset.
  • Evening Passeggiata: Stroll through the main street in the evening, enjoying the local atmosphere.
  • Gelateria Snoopy: Don’t miss the ice cream at this renowned gelateria.
  • Dining Recommendations: For a romantic dinner, try La Buccaccia or Osteria del Teatro. On a hot summer evening, dine alfresco at La Loggetta overlooking the main square. For a casual lunch, visit Enoteca Molesini.

Detailed Things to Do in Cortona, Italy

Explore Cortona’s Rich History and Cultural Heritage:

Cortona is steeped in history, with numerous landmarks that showcase its rich cultural heritage. Begin your exploration with a visit to the Etruscan walls, which date back to the ancient civilization that once thrived here. The Church of San Francesco, with its Gothic architecture and serene atmosphere, is another must-see. Don’t miss the Museo dell’Accademia Etrusca, where you can delve into the town’s past through its extensive collection of Etruscan artifacts, medieval manuscripts, and Renaissance paintings.

Visit the Monastery of Camaldoli:

For a unique blend of spiritual and natural beauty, head to the Monastery of Camaldoli. Nestled in the serene Camaldoli Woods, this peaceful retreat offers visitors a chance to connect with nature and spirituality. The monastery is a short drive from Cortona, making it an ideal destination for a day trip.

Discover the Local Cuisine:

Tuscany is renowned for its delicious cuisine, and Cortona is no exception. The town boasts numerous restaurants and food markets where you can sample traditional Tuscan dishes, such as pici pasta, ribollita, and bistecca alla fiorentina. For a more immersive experience, consider taking a cooking class or joining a food tour to learn about local ingredients and cooking techniques.

Go Wine Tasting:

As part of the Chianti wine region, Cortona is surrounded by vineyards that produce some of Italy’s finest wines. Many local wineries offer tastings and tours, providing an excellent opportunity to sample a variety of wines and learn about the winemaking process. Whether you’re a seasoned wine connoisseur or a casual enthusiast, a wine tasting tour in Cortona is a delightful experience.

Take a Walk in the Beautiful Countryside:

The Val di Chiana valley, with its rolling hills, forests, and vineyards, offers numerous walking and hiking trails for nature enthusiasts. These trails provide stunning views of the countryside and a chance to explore the natural beauty of the region. A walk through this picturesque landscape is a perfect way to unwind and connect with nature.

Shop for Local Artisanal Products:

Cortona is home to many artisanal shops and markets where you can find unique local products. From ceramics and leather goods to handmade jewelry and wine, there’s something for everyone. These shops offer a great opportunity to purchase souvenirs and gifts that capture the essence of Tuscany.

Attend a Local Festival or Event:

Cortona hosts several festivals and events throughout the year that celebrate its cultural heritage. The Cortona Mix Festival, which features a blend of music, literature, and art, and the Festa dei Candelieri, a traditional candle procession, are just a couple of examples. These events provide a vibrant glimpse into the town’s traditions and community spirit.

Visit Lake Trasimeno:

Just a short drive from Cortona, Lake Trasimeno is the largest lake in central Italy. This beautiful lake is a popular destination for swimming, boating, and fishing. You can also explore the lake’s small islands, such as Isola Maggiore and Isola Polvese, which are accessible by boat. A visit to Lake Trasimeno is a refreshing escape into nature.