After a leisurely breakfast the day began with a climb back up to the main road at Vagliagli.
Beyond Vagliagli the road descends past the ancient fortress of Aiola which last saw active service in the 16th century.
The solid walls of the fortress are capped by a Renaissance villa ... so conversion of old Tuscan buildings has a long history.
The road continues to descend to a large lake then runs alongside the Arbia for a few kilometres before beginning to climb towards the hill town of Radda in Chianti.
Radda in Chianti is sited some 540 metres above sea level and like most hill top towns in Tuscany offers spectacular views of the surrounding countryside.
The first priority after the climb was a refreshing drink ... fortunately Radda is well supplied with cafés.
After quenching my thirst I explored the back streets and alleys of this small town.
The town has an elliptical plan ... so almost no street is straight.
The narrow high sided alleyways provide a cool and quiet escape from the sun, and at almost every turn you get glimpses of the nearby countryside.
The next priority was lunch. Bar Sandy, just outside the old walls, has views back down the hill I had just climbed ... and allowed me to forget the hills ahead.
From Radda my route first took me down into the valley of the Torrente della Piana.
Just outside the town is the headquarters of the Chianti Classico Wine Consortium. Their symbol the black cockerel, once the emblem of the ancient League of Chianti, is displayed all over Tuscany.
The League is still in existence ... but instead of defending their lands against military invasion ... it aims to protect the environment.
Just outside Radda the road signs indicated that it was 29 kilometers to Siena ... I seemed to have done more than 60.
At the head of the valley is the large estate of the Villa Vistarenni. The villa stands on the site of an Etruscan settlement and the original cellars excavated from the rock over 1,000 years ago are still in use.
The villa contains apartments for hire ... with the optional use of mountain bikes.
After leaving the Villa I was lucky to avoid a heavy downpour ahead.
After splashing through the puddles I crested a ridge to get a last view of Radda in the distance.
From the ridge the final kilometres to Gaiole in Chianti were mainly downhill.
In Gaiole I turned to climb up to the 12th Century church of Pieve di Spaltenna.
This simple Romanesque church has a dramatic view over the Radda valley.
Luckily for me the adjacent monastery, Castello di Spaltenna, has now been converted into a very comfortable hotel.
Kirby James
