Arrive in Città di Castello, Umbria’s northern-most town and the largest town in the Tiber valley. Be sure to arrive early to have enough time to explore and discover this charming city, which will surprise you with its many artistic treasures including the Palazzo del Podestà overlooking other palazzi on Piazza Matteotti and the Cathedral of San Florido, which gathers together a multitude of architectural styles. Don't miss the view of the Umbrian hills from the top of the Civic Tower, before celebrating the first day of your trip with a dish of white truffle, a prized local delicacy, and perhaps a glass of Montefalco Sagrantino wine amidst monuments dating back to Roman times.

Meals:  Nil

After a short transfer* you walk through a shady wooded area to Pietralunga, a rural village at 566m altitude. The old town, with its steep narrow streets, the church of Madonna dei Rimedi and Pieve di Urbino are worth a visit. *You can be dropped off at two different spots, usually Campanile, and thus choose between a short or longer walk today. Distance 15km/9.3mi, Ascent +614m, Descent -655m

Meals:  B,D

From Pietralunga the trail leads you through a scenic landscape passing the monasteries of San Pietro and San Benedetto. The abbey of San Benedetto, dating from the XII century, was once an important reference point for pilgrims. The final stretch from Mocaiana to Gubbio is by taxi. Distance 18km/11mi, Ascent +547m, Descent -712m Time permitting, Gubbio is worth an extended visit - it is a beautifully preserved medieval town, with impressive buildings and churches. Be sure to learn of St Francis' time here, making a deal with a wolf which had terrorised the town and converting many people as a result. The wolf's remains are said to be in the Church of St Francis of the Peace just outside the town. Many traditional festivities are still honoured in Gubbio today. You can add an extra night here if you wish - please ask for our rates (must be added at time of booking.)

Meals:  B

Today is a long walk, so after breakfast, catch the bus to the start of the walk. You will walk along the hills which separate Gubbio from Valfabbrica. It is possible to shorten the walk by taking a transfer (of about 2km). The trail offers breathtaking views to Mt Sibillini, and as you walk you will appreciate why St Francis so loved the Umbrian countryside. Continue through a beautiful valley on the “Sentiero Francescano” to Valfabbrica, a quiet town which was an important fortress in the Middle Ages. The towers and part of the walls are well preserved. Dinner is included tonight. Distance 23km/14mi, Ascent +336m, Descent -336m

Meals:  B,D

This morning you can enjoy breakfast (own expense) at one of the local bars before setting off. It's another day of delightful countryside along Umbrian hills, walking from Valfabbrica. Assisi appears during the middle of the walk from a wonderful panoramic viewpoint over the edge of the hills. At the end of the hills you can enjoy the surrounding landscape with woods, fields, country houses and parish churches, all overlooked by the dramatic Apennine peaks above. A shorter walking day, you'll have time to explore hilltop Assisi, birthplace of St Francis and spiritual home of the Franciscan religious order. There are many points of interest to discover including outstanding churches, palaces, artwork and ancient buildings: the Basilica of St Francis and crypt, the Church of Santa Chiara, the Cathedral of San Rufino and the Minerva Temple built in Roman times. Then take time out in a small piazza to absorb the atmosphere of this charming town. Distance 13km/8mi Ascent +578m Descent -498m

Meals:  Nil

The trip concludes after breakfast, stay an extra night (ask for our rates) or continue on the next stage to Spoleto.

Meals:  B