Welcome to Hooked on Walking Holidays and our walking holidays in Italy. This particular hiking vacation in Italy is a level 2 self guided walking tour. Your walking holiday starts from stunning town of San Leo perched on a cliff overlooking the Marecchia valley, a short distance from Rimini. You 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 east most stretch of Tuscany The footpaths will then take us across the rich meadows of the Apennine mountains 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. 

Available on Wednesdays and Thursdays from April to October
Level 2 self guided tour.

Day 1 Arrival to Sam Leo, Explore the Old Town

You will be met in Rimini and transferred to your hotel in San Leo. San Leo, known in the past as Montefeltro (Mons Feretrius), is perched on a impressive 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 century by order of Federico lll da Montefeltro. The town was the base of the Contea di Montefeltro (Montefeltro County) and the place of civil and military battles for ages, it become the capital of Italy with Berengary II  (962-964).

Day 2  S.Leo – Montecopiolo 9.4 miles 15 km 4.5 hours

Today from the San 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 flank of Mount Carpegna which is celebrated for its mushrooms and forest fruits.

Day 3  Montecopiolo – Frontino 10 miles 16 km 4.5 hours

Today a beautiful walk presenting a varied landscape from the forested slopes of Mount Carpegna to the farmlands of the Montefeltro and to end in the quaint little medieval village of Frontino.

Day 4 Frontino – Sasso di Simone 8.8 miles 14 km 4 hours

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 plateau like summit and its wonderful vast views, it was one a site of ancient Pagan cults, an Abbey and the place where in the 16th Count Cosimo I de’ Medici, wanted to build a town; the Sun City

Day 5 Sasso di Simone – Badia Tedalda 10 miles 16 km 4.5 hours

Today the main highlights of your walk today include views from the wooded Apennine mountain’ 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.

Day 6 Badia Tedalda - Sansepolcro 11.2 miles 18 km 5.5 hours

Today 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 surroundings of the Upper Tiber Valley are lovely and tasty “secrets” of the local wood such as truffles and mushrooms are a must here.

Day 7 Departure
End of tour after breakfast.

Difficulty: This is a level 2 tour with walks up to around the 5 hour mark maybe 6 hours for slower walkers but the terrain is not hard.

Accommodation: A mixture of very nice 3 star hotels, guest houses and B & B’s

2010 Prices

How to get there
The best airport to use is Rimini where a transfer to San Leo is included. You can also fly to Bologna and then by train to Rimini.
Departure by bus plus and train is available to reach Florence and Rome. Direct Bus departures are available to get to Rome and Florence.

To view other walking holidays in Italy Sicily , Piemonte , Umbria , Cinque Terre , Dolomites , Sardinia, Amalfi Coast, Island of Elba , Sicily Active Volcanoes

Click below to view our
Cycling Holidays in Italy

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