On the Road: Distance: 104km I 65mi I Elevation: 1727m I 5666ft

We headed straight out of Siena into the Val d’Orcia, a stunning UNESCO recognised landscape. The riding is rolling but this is truly the idylic Tuscany imagined when people dream of visiting the area. We rolled through Asciano, San Giovanni d’Asso and Montisi to Pienza for lunch. Known as the “Ideal City” it is a nice place to pause and appreciate this exceptional region. From lunch we immediately climbed a 22% cobblestone 0.5km into the old town of Pienza, then we rode along the top of a ridgeline before plunging into Montepulciano and beyond to the plain, as we crossed towards Umbria and Trasimeno, where Hannibal again came up against a formidable Roman army. We are in Tuscany one more night at the beautiful medieval hill-town of Cortona which tested our legs at the end of a rolling day! It was a 5km, 6% grade uphill finish! Not only that, but in both leaving Siena and entering the old city of Cortona we had to manoeuvre around tourists wandering aimlessly for a km or two.

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Field Notes – Val d’Orcia

The magnificent natural scenery of the Val d’Orcia that extends through the Tuscan hills was inserted onto the UNESCO World Heritage List in 2004. Val d’Orcia fuses art, landscape and ecosystem in one geographical space, and is the expression of a series of marvelous natural characteristics. It is also the result of and testament to the people that has long-inhabited it. In fact, according to UNESCO this Valley is an outstanding example of the way in which a natural setting was redesigned during the Renaissance (14th-15th Centuries), reflecting the ideals of good governance in the Italian City-State. Additionally, these splendid localities were celebrated by the painters of the Sienese School, which flourished between the 13th and 15th Centuries.