Peter Bridge wrote, but I <snip>: PB: To find accommodations, I would google search "B&B" or "agriturismo" along with the names of nearby towns. Gaiole is in the heart of the impact zone of Chianti tourism, and prices and availability will reflect that. I suggest looking further out. Do some research work, and you will be rewarded.
HS: We went the same year as Der Listmeister, and stayed in two different Agroturismo places. The first was simply divine - on an organic olive farm - and the second was acceptable. Stayed a few nights at each, and use the car for touring during the day - sometimes leaving it at a train station to go into The City. Heartily recommend this.
PB: You will want to have a car while you are in the countryside. (Gaiole is in the countryside.) This item borders on non-negotiable, unless you are willing to completely sacrifice your flexibility.
HS: Of course, Bob Freeman and his lovely spouse did the whole thing (from Florence, as I recall) by bike.
harvey sachs
mcLean va