The Via Romea from the Adriatic Coast to the Tiber Valley

A walking tour from San Leo to Sansepolcro. 7d-6n



Tour Category

Self Guided Walking Tour


Tuscany, Le Marche


From stunning town of San Leo perched on a cliff overlooking the Marecchia valley we will follow the ancient paths of the pilgrims heading to Rome crossing the rugged highlands of Montefeltro, the legendary land of the Duke Federico da Montefeltro, a land dotted by Castles and Medieval hamlets providing a living legacy of its past. The Duke Federico was an important patron for many Renaissance artists who made of the area of Urbino a second artistic centre after Florence. We will then cross the border entering from Le Marche to Tuscany coasting the slopes of the Sasso di Simone, an impressive limestone rock dominating meadows and beech tree forests once the site of the “Sun City”  today as in the past the eastmost stretch  of Tuscany.  The footpaths will then take us across the rich meadows of the Apennine Mts   where Chianina cows graze to the forested ridges of the Alpe della Luna “the Moon Alp” to descend in the Valtiberina Toscana, the Tuscan Upper Tiber Valley  often remembered and depicted by the artists like Piero della Francesca where the Medieval and Renaissance town of Sansepolcro lies.


Arrival to S.Leo, Explore the Old Town (2km)
S. Leo: known in the past as Montefeltro (Mons Feretrius), is perched on a unattackable massive rock, you can access it only by a narrow road carved on stone. On the highest point you have the Fortress projected by Francesco di Giorgio Martini, in the 15th C. by order of  Federico lll da Montefeltro.  The town was the base of the Contea di Montefeltro (Montefeltro County) and place of civil and military battles for ages, it become capital of Italy with Berengary  II  (962-964).
Walk Details: Easy – 2 km exploratory walk in the main roads and narrow alleys of town.

Day 2: S.Leo – Montecopiolo

Today from the S. Leo cliff you will walk towards the hills passing from a prevalent agricultural area to a more forested territory and dedicated to stock raising. The area of Montecopiolo lies on the eastern flanck of Mt Carpegna it is celebrated for its mushrooms and forest fruits.
Walk Details: Moderate – approx 15 km walk mostly ascent through gravel roads and footpaths.

Day 3: Montecopiolo – Frontino

A beautiful walk presenting a varied landscape from the forested slopes of Mt Carpegna ( Carpegna from Carpino = Hornbeam) to the farmlands of the Montefeltro to end in the quaint little Medieval village of Frontino.
Walk Details: Moderate – approx 16 km rolling hike mostly descent

Day 4: Frontino – Sasso di Simone

Today you’ll experience a stunning walk across the meadows and woods of the Sasso di Simore Natural Reserve. The Sasso di Simone and the smaller Simoncello are 2 stunning limestone rock formations raising from the clay ravines and the forests of the area. The Sasso di Simone has always been an inspiring site for its flat plateaulike summit and its  incredibly vast views, it was one a site of  ancient Pagan cults, an Abbey and the place where in the 16th C. Cosimo I de’Medici, wanted to build a utopic town; the Sun City
Walk Details: Moderate – 14 km; 10 km rolling hike reaching the base of the Sasso then a gradual descent towards the valley

Day 5: Sasso di Simone – Badia Tedalda

Highlights of this day include views from the wooded Apennine Mountains’ ridge and a walk across footpaths coasting meadows, wheat fields and forests to the Marecchia river valley and the Abbey of the Tedaldi (Badia Tedalda) that dominates the valley.
Walk Details: Moderate– approx 16 km (paths, double tracks and gravel roads).

Day 6: Badia Tedalda – Sansepolcro

From the meadows of Badia you will reach the forested ridges of the Apennine through paths used by Pilgrims, Soldiers and Saints like St. Francis you will gradually enter the scenic Tiber valley. The vista of the Upper Tiber Valley is lovely and the tasty “secrets” of the local wood such as truffles and mushrooms are a must here.
Walk Details: Moderate/Difficult – approx 18 km (paths, double tracks and gravel roads).

Day 7: Ciao Ciao!

End of tour after breakfast. Departure by bus plus train is available to reach Florence and Rome. Direct Bus departures are available to get to Rome and Florence.


Contact us to request more information or to make a booking