Cycling day trip from Gubbio to Assisi

Get ready for a gorgeous—and challenging—ride through the heart of Umbria! Starting in the medieval town of Gubbio, known for its stunning Roman theater, winding stone streets, and the traditions of the Corsa dei Ceri festival, you’ll head south towards the equally historic hill town of Assisi, birthplace of Saint Francis and a UNESCO World Heritage Site.

The route covers a bit over 63 km and packs quite a punch when it comes to elevation—you’ll climb over 2,200 meters and descend nearly the same, with the highest point reaching just under 780 meters. Most of your ride will be on quiet country roads, but you can expect plenty of variety under your wheels: plenty of smooth pavement, with some sections of paving stones, gravel, and occasional rougher surfaces.

You’ll roll through rolling hills, olive groves, and patchwork fields, with panoramic views that make every climb worthwhile. Arriving in Assisi—with its iconic basilicas and pink-stone skyline—is a pretty epic way to finish. Don’t forget to grab a gelato in the piazza to celebrate!