Best attractions and places to see around Cortona include a rich tapestry of historical, cultural, and natural sites. This hilltop town in Tuscany offers panoramic views of the Val di Chiana, Lake Trasimeno, and the surrounding countryside. Visitors can explore ancient Etruscan landmarks, Renaissance art, and medieval architecture. The area provides diverse opportunities for outdoor activities amidst olive groves and vineyards.
Last updated: May 9, 2026
Highlight (Segment) • Cycleway
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Highlight • Monument
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Highlight • Lake
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I walked the stretch from Borghetto to Castiglione del Lago (8/9 km) and was a little disappointed that you only see the lake once and... watch out for cyclists coming in the opposite direction.
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A circular route of approximately 60 km. Completely on a dirt track (only 2 km on the road). The route is exclusively for cyclists and pedestrians, immersed in nature, with breathtaking views, and from San Feliciano you can see sunsets that heal the soul, so beautiful they are, absolutely worth doing.
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Also ideal for gravel bikers! More tips for gravel bike adventures in the area at https://graveldeluxe.com or in my Komoot profile https://www.komoot.de/user/graveldeluxe
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Also ideal for gravel bikers! More tips for gravel bike adventures in the area at https://graveldeluxe.com or in my Komoot profile https://www.komoot.de/user/graveldeluxe
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Also ideal for gravel bikers! More tips for gravel bike adventures in the area at https://graveldeluxe.com or in my Komoot profile https://www.komoot.de/user/graveldeluxe
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Magic nightride! Thnx for sharing this route. I started this ride anti clockwise 20.30hr in late June. Next to the great views over the lake at sunset it started to get dark when passing Liciano Niccone (So bring some good light with you) From there the last climb trough the forrest was pure magical. At both sides of the road the forest was full of fireflies. Quit some stunning experience!
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Nice cycling experience but better with a MB! On some sections coarse gravel so chance of punctures is considerable!
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Beautiful white road on the cycle path
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Cortona is rich in history. You can delve into ancient Etruscan history at the MAEC - Museum of the Etruscan Academy and the City of Cortona, housed in the 13th-century Palazzo Casali. The Diocesan Museum, located in Piazza del Duomo, showcases Renaissance masterpieces by artists like Fra Angelico and Luca Signorelli. Don't miss the Basilica of St. Margaret, dedicated to Cortona's patron saint, offering both spiritual significance and panoramic views.
For breathtaking panoramic views, head to the Fortress of Girifalco (Fortezza Medicea), perched at Cortona's highest point. The well-preserved Etruscan Walls surrounding the town also offer scenic walks with expansive vistas. Additionally, Piazza Garibaldi provides a wide view of the Val di Chiana, Lake Trasimeno, and Montepulciano.
Yes, the area around Cortona is excellent for cycling. The Lakeside Cycle Path – Loop around Lake Trasimeno offers a scenic ride, with sections like the Gravel paths on the Lake Trasimeno cycle route providing typical dirt but compact roads between cultivated fields. You can find more cycling routes, including gravel biking and MTB trails, in the Gravel biking around Cortona guide and the MTB Trails around Cortona guide.
Cortona's elevated position provides stunning views of the Val di Chiana, terraced olive groves, and vineyards. Lake Trasimeno, Italy's fourth-largest lake, is visible on clear days and offers opportunities for water sports and exploring charming towns. The idyllic countryside is perfect for hiking or biking through olive groves and oak forests, with popular routes like the Sentiero Frassino.
Many attractions around Cortona are suitable for families. Exploring the narrow, winding cobblestone streets of Cortona's Historic Center is an adventure in itself. The Lakeside Cycle Path – Loop around Lake Trasimeno and the Gravel paths on the Lake Trasimeno cycle route are generally family-friendly for cycling. The Castiglione del Lago Lakeside Sculpture is also a pleasant spot accessible from the cycle path.
The surrounding countryside of Cortona is ideal for outdoor activities like hiking and biking. Spring (April-May) and autumn (September-October) generally offer pleasant temperatures for exploring. During these seasons, the weather is mild, and the landscapes are particularly beautiful with blooming flowers or vibrant fall foliage, making it perfect for enjoying the panoramic views and trails.
Absolutely. The idyllic countryside around Cortona is perfect for hiking or running through olive groves and oak forests. You can find various running trails in the Running Trails around Cortona guide, with options ranging from moderate to difficult. Popular routes include the Sentiero Frassino and the Cammino di San Francesco.
Cortona has a deep Etruscan heritage. The town is surrounded by well-preserved Etruscan Walls, and the MAEC - Museum of the Etruscan Academy and the City of Cortona houses an extensive collection of Etruscan artifacts, including the famous Tabula Cortonensis. Just outside the town, the Archaeological Park of Sodo features Etruscan tombs, such as the 'Melone tumulus,' offering a glimpse into archaic Etruscan funerary architecture.
Visitors particularly appreciate the stunning panoramic views from locations like the Basilica of St. Margaret and the Fortress of Girifalco. The serene atmosphere of the Lakeside Cycle Path – Loop around Lake Trasimeno and the charm of the medieval streets are also highly praised. The blend of historical sites, cultural treasures, and natural beauty consistently receives positive feedback.
Cortona is home to several significant religious sites. The Basilica of St. Margaret, dedicated to the city's patron saint, is a prominent landmark. The Cortona Cathedral (Santa Maria Assunta), with its Romanesque, Gothic, and Baroque elements, is another key site. Additionally, the Monastery of Saint Francis 'Le Celle' is one of the earliest monasteries established by Saint Francis of Assisi, known for its serene atmosphere.
The Lakeside Promenade of Passignano sul Trasimeno is a relaxing spot on Lake Trasimeno, perfect for a short stop. It's an essential point on the tour of Lake Trasimeno, offering beautiful views and opportunities to visit the village of Passignano, which is worth exploring.
Yes, Cortona's historic center is highly walkable. It features narrow, winding cobblestone streets and steep alleyways, making it ideal for exploration on foot. Wandering through these medieval streets is an experience in itself, allowing you to discover hidden corners and admire the ancient architecture.


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