From the classic rolling hills South of Siena we will cross the “Tuscany’s breadbasket” the Chiana Valley mostly farmlands and rather big fields a wide valley that separate the curvaceous hills of Montepulciano from the pre-Apennine mts to the town of Cortona located in the middle of the slope almost a balcony over the valley. Cortona is a stunning old town with an history that dates back to Etruscan times (from 8th to 7th c. It became an important Etruscan city state) and a noble Medieval soul. From Cortona we will then change totally scenery entering in the pre-Apennine mountains and passing from ever green oak woods and olive groves to mountain meadows and the rugged scenery of this highlands where Hannibal the Carthaginian approached the northern coast of Lake Trasimeno where we defeated the Romans. We will then decend into Northern Umbria with optional routes through the Mountains or the Valleys to end up getting back to Tuscany again entering the Eastmost corner of the region where Sansepolcro is in the Upper Tiber valley. The Upper Tiber Valley has just East of it the Apennine mts, the actual mountain divide of the area with many many kms of gravel and dirt roads crossing beech tree, oak woods, mountain meadows, medieval monasteries and hamlets. On the Last day we will cross the pre-Apennine ranges to get to Arezzo with 2 different routes.
Day 1: Meet our guide at the hotel, he will give you an introduction of the tour presenting all the information and material used in the tour.
Day 2: Montepulciano – Cortona
52.2 km +384m
Easy ride, no technical sections, no steep sections. Mostly gravel roads and mule tracks. From Montepulciano we will descend through the wine production territory of the Vino Nobile, some interesting estates are on the way, then once we hit the valley (8 k approx) we will take some minor roads and gravel roads to join the main bike path ( in gravel) that runs parallel to the Canale Maestro della Chiana canal (15 k approx), we will keep riding parallel to that until we reach the outskirts of Foiano della Chiana ( 35k approx), this village can be an ideal short detour for a lunch break. From there we will leave the canal to get into another bikepath in gravel to Cortona, the actual path ends next to an Etruscan Tomb which may be interesting to check, once we are below the Cortona’s hill we will climb for 5 km to the old town on an asphalt road.
Day 3: Cortona – Sansepolcro
63.3 km +1442 m
Difficult ride with some technical sections and steep inclines, from Cortona we will start climbing on the main asphalt road then after approx 5 km we will take gravel road that will cross Monte Sant’Egidio taking us to the saddle between Chiana valley in Tuscany and the Upper Tiber valley in Northern Umbria, from there we will descend towards Castiglion Fiorentino and take a gravel road that after 4 km turns into an uneven dirt road to the area of Mt Favalto (approx 1000 mts), from there we will then stay in the ridges and eventually descend NE to the Tuscan Tiber valley where Sansepolcro is.
Cortona – Sansepolcro easy
Easier version presenting only the 1st climb to cross Mount Sant’ Egidio then following asphalt and gravel roads of the valley and incorporating Città di Castello as main centre of the area.
Day 4: Sansepolcro – Alpe della Luna – Sansepolcro
38.8 km +1193m
Moderate ride, no technical sections, mostly on gravel roads, and uneven gravel roads with most of the ascent on asphalt. From Sansepolcro we will ride towards Rimini taking the road to the Via Maggio mtn pass then before thw actual pass we will leave the asphalt (at approx 16k) for an uneven gravel road, very scenic with stunning vistas over the Tiber valley, at 27 km there is a small sidetrip to a donkey farm where you can set up a pic-nic or have a meal at the local inn. The return to Sansepolcro is mostly on a wide gravel road than at the very end turns asphalt.
Day 5: Sansepolcro – Pietramala - Arezzo
34.6 km +868m
Moderate – Difficult ride, some technical section and steep inclines all in the 3 km around the ruins of Pietramala. From Sansepolcro we will move west, pass the Tiber river and follow it upstream in the minor gravel and asphalt roads, after 8 km we will cross the medieval hamlet of Anghiari and continue W crossing the Sovara creek and climb towards the Pre-Apennine range at km 20 we have reached the top and a couple of km later we will start the technical steep descent and ascent around Pietramala ( this is a ruined stronghold belonging to the famous lords of Arezzo Tarlati di Pietramala (XIII and XIV c.) then a gentle descent that will take us through the Wine Estates of S. Fabiano and further down to the valley where Arezzo lies.
Day 6 : Ciao Ciao !
The tour ends after breakfast