Day 1: Arrival in Cortona
We meet in Cortona. We’ll have a late af ternoon orientation and bike fitting. Book your f light into Florence or Rome and there is good train service f rom both cities to the start of the trip. Cortona, the setting f or Francis Mayes’s best seller, Under the Tuscan Sun and a beautif ul hill town to
begin our tour.
Day 2: Cortona – Citta di Castello – Distance: 52 km, elevation gain: 720 meters
We’ll take the backroads departing the Tuscan countryside and enter Umbria. We will cycle among the green hills of the Upper Tiber Valley, in luminous landscapes and an intensely cultivated countryside, to the art city of Città di Castello. Enclosed in a ring of Renaissance walls and surrounded by arable farmland, Città di Castello’s streets are lined with grand palaces, yet still has a genuine, lived-in charm. The town occupies the site of ancient Tiberinum . We’ll
spend 2 nights here.
Day 3: Citta di Castello – loop ride Distance: 40 km, Elevation gain: 645 meters
On our loop ride we’ll visit the many small villages with a highlight being, Santa Maria Tiberina. Full of charm, this village is described as having ancient Etruscan roots but a fully medieval heart. It is situated in a very panoramic position, offering unparalleled views. Fortresses and castles dot the summits. In between are patches of olive groves and vineyards. It’s a postcard -like setting.
Day 4: Citta di Castello – Sant’Angelo in Vado Distance: 48 km, Elevation gain: 875 meters
Sant’Angelo in Vado is one of the most f ascinating places to visit in the province of Pesaro e Urbino. The town is of Roman origin and located in the high valley of the Metauro River and surrounded by some of the most the picturesque countryside of Le Mar che region. The original Tif ernum Mataurense can still be seen f rom the spectacular ruins of the ancient Roman Villa of Domus del Mito with its magnif icent mosaics which date from the I century BC. This is the most important archaeological f ind of the last 50 years in this the region.
Day 5: Sant’ Angelo in Vado – Urbino Distance: 46 km, Elevation gain: 650 meters
Winding countryside roads take us to Urbino. Perched high up on one of Le Marche’s hills, Urbino is a city that delights both history buff s and foodies. Its architecture, art, and history rival any of Tuscany’s f amous masterpieces and you’ll surely understand why this is a UNESCO Heritage Site.
Day 6: Urbino – Gradara Distance: 50 km, Elevation gain: 700 meters
Today’s ride takes us across the region of the Marche to the border of the Northern Italian region of Emilia-Romagna and then we return to the Marche to the fortified medieval village of Gradara. With a majestic castle that, throughout the centuries, has been home to some of Italy’s most famous noble families, Gradara is a delight to explore. Especially, if you have always wanted to find yourself in a fairytale-like medieval setting that was declared Italy’s most beautiful village in 2018.
Day 7: Gradara to Pesaro – Distance: 30 km, Elevation gain: 450 meters
Today’s ride takes us to Pesaro on the Adriatic coast. We enter the town on a bike path and get to see f first-hand why Pesaro is known as the”City of Bicycles”, thanks to its big net of bicycle paths. Pesaro received this award by Legambiente, the most important ecologist society in Italy, in 2015, because it is the city with the biggest bicycle use in Italy. We will spend our f inal night at Hotel Vittoria, the most charming hotel in the town with its own private beach.
Day 8: Departure
There is a train station in Pesaro and we can also assist with transfer suggestions to Florence, Bologna, Rome and Venice airports are all options.