We assemble on this first day of our trip at our base in Perugia, get a proper bike fit, share a first lunch, then head out for a ride to the north towards the beautiful Lago Trasimeno, but not without meandering a bit across hillsides overlooking the area before dropping to the lake and ending on a pier in Torricella. We’ll enjoy the shoreline village for a bit, possibly with a cooling dip, then load the bikes and return by van to Perugia. Our home this evening is the beautiful Locanda della Posta Boutique Hotel, in the heart of historic central Perugia. Tonight, we share a dinner and begin to form bonds with our fellow Nomads; tomorrow, we continue our journey through Umbria.

We’ll leave Perugia and take a circuitous route through the Apennine Mountains north and east, then return to the western slope village of Assisi. As is our custom, we’ll travel on smaller lanes and paths and go cross-country wherever possible. We’ll seek out the most authentic places, places that tell the history of the centuries that formed them.

People of faith have been making pilgrimages to Assisi since its most famous native son, known now as Saint Francis of Assisi, was canonized a saint in 1228. Revered as a healer and lover of nature, Saint Francis has long inspired devotees to visit Assisi’s Basilica, seeking solace and healing. We’ll combine respect for Assisi’s religious heritage with its secular importance as one of the best examples of Umbrian hill towns. Assisi’s churches, castles, and piazzas remain true to their architectural heritage dating back to medieval times—and beyond.

The following day we’ll venture out again, this time heading directly east across lower hills that overlook the valley, and climbing to viewpoints in the nearby Parco Regionale del Monte Subasio before returning to our base in Assisi.

Our lodging for the two nights in Assisi is Hotel Sorella Luna, in the heart of the ancient village. Dinner each night  is on your own, or you can join the “Nomads Table,” a place where the Nomads team will welcome any who wish to join.

We leave Assisi this morning and head west, away from the Appenine Mountains. We alternately ride the valley floor and climb for views as our route meanders into and out of the hills. Following this path, we’ll better understand the nature of the Umbrian region, a blending of mountains and plains, hilltowns and villages, all in harmony with the natural beautiful of this amazing setting.

Our destination this day is the fabulous Villa Santa Barbara, located near another historic hilltown, Montelfalco. Our lodging is a 16th century summer residence, surrounded by the vineyards of Montefalco. Dinner will be on your own or you can join us at the Nomads table.

Montefalco sits on a hilltop in an area surrounded by agricultural valleys and forested hills. The Appenine Mountains rise the east, while an extended ridge rises to the west. We’ll explore that westward ridge today, finding time to visit more of the quaint hilltop villages that overlook the narrow valley to its west. The beauty of this high hill country, pastoral and rugged, is a feature of Umbria that is as much its core as the vast rolling meadows and valleys famous for endless orchards and vineyards. Umbria is a place of complexity and diversity; our hope is to understand and appreciate it just a little better.

Our lodging tonight is restored castle, Torre Sangiovanni Albergo e Ristorante, set on a perch overlooking the valley. On this, our final evening of our adventure through Umbria, we will gather for a shared dinner and toast the good fortunes that brought us together.

On our final morning, we’ll make our way west by bike or van into the valley and across another ridge, eventually finding Orvieto and its train station. We’ll bid farewell and wish you a life filled with more great adventures. Leaving Umbria this fall, the only thing on our minds will be the question of how soon we’ll return. And return we will.