Itinerary
- Day 1
Città di Castello
You'll arrive in Città di Castello, a town in Umbria with plenty of historic character to discover. Spend your first afternoon walking around the ancient Roman monuments scattered throughout the old center. Once you're settled into your accommodation, relax with a glass of local Montefalco wine and get oriented to your surroundings.
Optional Activities
- Explore Roman monuments in Città di Castello
- Taste Montefalco wine
Landmarks/POIs Città di Castello - Day 2
Città di Castello to Pietralunga
After a short transfer, you'll hike through wooded terrain heading toward Pietralunga, a rural village sitting 566 meters above sea level. The town itself has steep narrow streets worth exploring, and you can visit the Madonna dei Rimedi church plus the Pieve di Urbino while you're there. You can pick between a shorter or longer hiking route depending on how much walking you want to do.
- Meals
- Breakfast, Dinner
Included Activities
- Guided hike from Città di Castello to Pietralunga through wooded terrain
- Visit Madonna dei Rimedi church
- Visit Pieve di Urbino
Optional Activities
- Choose between shorter or longer hiking route
Landmarks/POIs Pietralunga Madonna dei Rimedi Church Pieve di Urbino - Day 3
Pietralunga to Gubbio
This morning you'll hike from Pietralunga past the monasteries of San Pietro and San Benedetto, passing by the 12th-century San Benedetto abbey which used to be a major pilgrimage destination. The route takes you through the Umbrian landscape with nice views throughout. From there a cab takes you the final section into Gubbio, where you'll have time to explore one of Italy's best-preserved medieval towns with its impressive buildings and churches.
- Meals
- Breakfast
Included Activities
- Guided hike from Pietralunga to Gubbio
- Visit Monastery of San Pietro
- Visit Monastery of San Benedetto
- Explore Gubbio medieval town
Optional Activities
- Extended visit to Gubbio churches and traditional festival sites
Landmarks/POIs Monastery of San Pietro Abbey of San Benedetto Gubbio 
- Day 4
Gubbio to Valfabbrica
You've got a longer hike ahead today along the hills between Gubbio and Valfabbrica, with views that reach all the way to the Sibillini mountains. You'll follow the scenic Sentiero Francescano trail through a beautiful valley in the heart of Umbria. There's an optional cab transfer available that can shorten the hike by around 2 kilometers if you need it.
- Meals
- Breakfast, Dinner
Included Activities
- Guided hike from Gubbio to Valfabbrica
- Hike along Sentiero Francescano
Optional Activities
- Transfer option to shorten hike by approximately 2km
Landmarks/POIs Valfabbrica Sibillini Mountains - Day 5
Valfabbrica to Assisi
After breakfast you'll hike over the Umbrian hills from Valfabbrica, a quiet town with medieval towers and walls still standing. The path takes you through countryside with woods, fields, farmhouses, and parish churches, with the Apennine peaks visible in the distance. By the end of the hike you'll reach a vantage point where Assisi comes into view behind the hills.
Included Activities
- Guided hike from Valfabbrica to Assisi
- Explore Valfabbrica medieval fortress
Landmarks/POIs Valfabbrica Assisi Apennine Mountains 
- Day 6
Assisi
Your hiking tour wraps up after breakfast. You can depart whenever you'd like, or if you want to stay longer you can continue exploring Assisi and the region around it on your own schedule.
- Meals
- Breakfast
Optional Activities
- Explore Assisi on your own
Landmarks/POIs Assisi
