Are there any bike tours (winery and/or olive) that originate in the Chianti area, instead of driving to Florence?
Why don't you contact these people to see if they have any information. I know the link takes you to a specific event but there's a "contact us" link and they have a presence in Gaiole year round, a town that appears to me to be the cycling centre of the universe. I would like to think they can help you. Certainly, whenever I am in Gaiole I see hoards of people setting off or coming back on bikes.