Our driver picked us up in Greve and deposited us on the side of the road of the “highest of the Chianti hills, Monte San Michel” so we could begin our trek into Radda. Our guidebook called this day an “easy” hike of 12km that should take 3 hours. It started with a delightful stroll through a forest.
The path seemed to be the cut line for water and gas pipes. The path itself was small stones and sometime bedrock. The footing was challenging, especially going downhill, which was most of the initial trek.
We stopped for lunch in Volpaia. It is a small village focused on wine and olive oil. We chose The Bottega for our meal as it had a commanding view of the countryside. The restaurant was attached to the church on one side. There was a bakery attached to the church on the other. It was a very good use of very old buildings. Everything looked like it had been there a long time, likely, according to the sign on the castle on the square, since 1176. 
we appreciated the restaurant motto but required beer to quench hiking thirsts
We learned that many of the paths we needed to take were outlined by massive cedars lining the routes. 
The walk away from Volpaia was through a farming community that teemed with butterflies and bees in lavender plants. 
The sounds of these insects were soothing and a welcome change from the ever present cicadas. We continued through vineyards, around churches and through fields and had a pretty good day. The reality of how the end of our day would go began as we stood at the top of a vineyard and looked across the valley to the top of the next “hill” and realized it was Radda. 
We were tired by this point and starting to be less enthusiastic about the remaining hike. I noticed the vineyard building at the bottom of the path and started to fantasize about it being a winery that did wine tastings and after we stopped for that tasting we could get a cab to the top. Our luck ran out as we realized it was closed on Sundays. Our only option was to climb. And climb we did, taking the “shortcut” option from our book. It meant an almost 2 km vertical climb up the hill. We did it with tortoise like speed.
We all compared our various trackers and realized we had actually walked 19 km and had been on the path for approximately 5.5 hours (including lunch). We sipped gin on the patio outside our rooms and relaxed feeling very accomplished. Dinner occurred after brief naps on another patio with a beautiful view. 