Umbria Cycling Holiday

Touch down in the spellbinding town of Assisi, where ancient stories echo through cobbled streets and spiritual history meets scenic charm. This UNESCO World Heritage gem is your gateway to Umbria. Wander through winding alleys and stumble across hidden piazzas, each one whispering tales of Saints Francis and Clare. Marvel at the grandeur of the Basilica of St. Francis, explore the Roman Temple of Minerva, and soak up the serenity that wraps around this hilltop town. In the late afternoon, it’s time to meet your trusty steed—your bike, that is. After a relaxed fitting and a route briefing, you’ll settle in for the night at a cosy 3- or 4-star hotel just steps from the old town.

Your wheels hit the road with a peaceful morning pedal to the charming village of Spello. From there, ride through the sun-drenched valley of Spoleto, passing the bustling town of Foligno before the road rises to Montefalco—affectionately called the “balcony of Umbria.” The views are jaw-dropping, and the frescoed Franciscan church museum is well worth a peek. Descend into Bevagna, where medieval magic lives on in its perfectly preserved square and Romanesque churches. The day wraps up in Torgiano, a hilltop haven with a brilliant wine museum and tempting tastings at Lungarotti. You’ll rest your legs in a stylish 3- or 5-star hotel.

Distance: 64 km | Ascent/Descent: +552m

Today’s ride takes you to Perugia, the lively capital of Umbria, buzzing with Renaissance art, ancient arches and café culture. This hilltop city is bursting with character, from its medieval old town to its vibrant piazzas. After soaking up its energy, you’ll glide back to the peaceful lanes of Torgiano for a second night in this wine-loving gem.

Distance: 34 km | Ascent/Descent: +503m

Set off from Torgiano and meander through softly rolling hills, where every pedal stroke brings you closer to Lake Trasimeno’s shimmering shoreline. The reward? A breathtaking panorama of Italy’s fourth-largest lake, dotted with islands that seem to float in time. Ride through the sleepy fishing village of San Feliciano—where ferries drift lazily toward Polvese Island—then follow the gentle crunch of gravel paths all the way to Passignano. This lakeside gem is where history and nature dance in harmony. Wander its historic lanes, stretch out on the beach near the town centre, or hop over to the charming Isola Maggiore for a splash of island life. Tonight, you'll stay in a welcoming 3- or 4-star hotel, just steps from the water.

Distance: 51 km | Ascent/Descent: +472m

It’s time to trade lake views for unspoiled hills and medieval towers as you ride toward the tranquil town of Umbertide. The route winds up to Castel Rigone, perched high above the lake with knockout views in every direction. From here, it’s pure joy riding along a scenic ridge before descending smoothly into the Tiber Valley. Umbertide welcomes you with its iconic 14th-century tower and a sense of quiet charm. Tonight, you're tucked away just outside town in a country hotel with a fantastic on-site restaurant and a pool that’s perfect for a refreshing dip after a rewarding day in the saddle.

Distance: 47 km | Ascent/Descent: +837m

Roll out of Umbertide and prepare for a day that’s all about classic Umbrian charm and big-sky views. Your first climb brings you to Montone, a little town where time seems to have slowed down just for you. Cobbled streets, quiet corners, and a view that makes every turn of the pedal worthwhile. From there, you’ll head on to Pietralunga, another sleepy hilltop hideaway, before descending into the majestic fortified town of Gubbio. With its Roman theatre, ancient palaces, and the monastery of Saint Ubaldo perched 827 metres above the town, Gubbio is an open-air museum with serious wow-factor. If you’re up for it, take the quirky cable car to the top and soak in those sweeping views. You’ll stay overnight in a cosy 3- or 4-star hotel near the historical centre.

Distance: 58 km | Ascent/Descent: +904m

Your final day kicks off with a punchy climb through Umbrian countryside that looks like it was painted just for you—rolling hills, patchwork fields, and silence that soothes the soul. After that early effort, enjoy the long, glorious descent into Assisi. This ride doesn’t just end with a bang—it rolls you right through the heart of the town. You’ll cruise past the monumental Basilica of St. Francis, the Temple of Minerva, and the Basilica of Saint Clare, each one a beautiful bookmark in your week-long story. Your journey comes full circle with an overnight stay in Assisi, giving you one last chance to soak up its spiritual charm.

Distance: 59 km | Ascent/Descent: +807m

Today we bid you arrivederci and will organise for your transfer back to the airport.