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Day 1: Arrival in Cortona
Arrival in Cortona, a charming medieval hill town made famous by Frances Mayes’ book Under the Tuscan Sun. With its narrow stone alleys, panoramic views, and timeless atmosphere, Cortona is the perfect place to begin your journey into the heart of Italy. Spend the night soaking in the town’s unique blend of history, culture, and Tuscan charm.
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Distance 52 km
Day 2: Ride to Borgo Mandoleto Solomeo along the Trasimeno Lake
Lake Trasimeno is surrounded by rolling hills dotted with olive trees and picturesque villages. Ride through Monte del Lago and the fishing village of San Feliciano, soaking in the tranquil atmosphere. You’ll spend the night in a charming country inn in Solomeo, a beautifully restored village known worldwide as the home of cashmere designer Brunello Cucinelli. A cooking class can also be arranged for those who wish to dive into local culinary traditions.
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Distance 37 km
Day 3: Borgo Mandoleto Solomeo loop
On this day, you can either enjoy some well-deserved rest or ride a beautiful 37 km loop through the countryside south of Solomeo, with the option (available by advance booking) to join a wine tasting at Monte Vibiano winery.
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Distance 25 km
Day 4: Borgo Mandoleto Solomeo - Perugia
Your day destination is Perugia, the main town in Umbria, with its fine square and communal palace, its renaissance painting collection, and the Rocca Paolina, the subterranean town. Perugia is also a lively town with shops and fashionable boutiques. Spend the night in town.
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Distance 35 km
Day 5: Perugia - Assisi
Today’s ride takes you deeper into the heart of Umbria, through gentle hills and quiet country roads dotted with olive groves and cypress trees. Your destination is Assisi, one of Italy’s most iconic spiritual and cultural landmarks. You’ll spend the night in a charming country inn just outside the historic center—close enough to walk to the Basilica and enjoy the peaceful atmosphere of this timeless hilltop town.
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Distance 50 km
Day 6: Assisi loop
You can enjoy a full day to explore the treasures of Assisi at your own pace—its cobbled streets, ancient churches, and breathtaking views. Or, if you’re in the mood for another ride, we suggest a scenic bike loop (about 50 km) to the town of Deruta, renowned for its centuries-old tradition of hand-painted ceramics. A perfect blend of culture, art, and countryside pedaling.
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Distance 37 km
Day 7: Assisi - Spello
Today’s ride takes you through the very heart of Umbria, from Assisi to the charming hill town of Spello, and then on to Bevagna—a beautifully preserved medieval village known for its cobbled streets, ancient squares, and a renowned summer festival that celebrates traditional crafts and history. Overnight in Spello.
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Day 8: End of our service
Transfer to Foligno train station to catch the train for the next destination. See you on your next adventure in Italy!
