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On bicycle in Val d’Orcia between the Middle Ages and Renaissance

This cycling itinerary in Val d’Orcia follows historical routes, more precisely the path that unites the Middle Ages and the Renaissance. Montepulciano: with its typically medieval structure which was developed during the Renaissance, the main gate still embedded in a section of the original city wall, the main street which twists and turns its way to the city square, with its turreted palace which is today the city hall, and which itself dominates the suggestive and irregular square. And nearby is the castle which guaranteed control and defence of the territory, situated so strategically as to cause dispute between Siena and Florence. And last but not least the historic wine cellars.
Much smaller, slightly more than 200 inhabitants, but just as evocative, is the hamlet of Montichiello, another example of medieval construction surrounded by a perfectly conserved wall connecting four imposing towers. Here, since 1967, the extraordinary experience of the “teatro povero”, a production that transforms the centre of the hamlet into a theatre under the stars and the inhabitants into writers and actors, who tell stories about historical and actual events that have affected their lives.
Next on the itinerary is Pienza, a renaissance jewel, the brainchild of Pope Pio II Piccolomini whose intention it was to build an ideal city, and indeed Pienza is known for the order and harmony of its construction. It is irresistible to tourists, but maintains its fascination even on the days when it is saturated with visitors.
Connecting these three hamlets is the background of the extraordinary panorama of the valley which gets its name from the river Orcia and which UNESCO has declared a World Heritage Site. For this itinerary we suggest two alternatives – one which includes both paved and unpaved roads with very little traffic and the other which uses only paved roads.


Departure and arrival: Montepulciano
Distance: 48 km
Type of road: paved and unpave
Total ascent: 770 m
Type of bicycle: preferably MTB (also trekking for cyclists who are not afraid of unpaved roads)


Departure and arrival: Montepulciano
Distance: 39 km
Type of road: paved
Total ascent: 680 m
Type of bicycle: trekking bike

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