Sorry, clarifications.
Rome is approximately an hour closer to the Siena/Gaiole area than is Milan, when one is driving. Maybe 2.5 hours. As my memory serves. Pisa is closer than Rome, but not so much that it really matters. Maybe 2 hours driving time. Having the option of Pisa or Rome will give greater flexibility when shopping for flights. The immediate Siena/Gaiole area is small, and driving distances are short.
>From Rome one can easily take a train to Siena and then pick up a car, but it would probably make sense to pick up the car immediately, assuming the ride is the next destination. Car rentals are easily arranged for p/u in one city and drop-off in another city.
Driving in Italy is generally fast and easy, but it's a battle to find one's way in large urban areas. When a trip is winding down, it may be easier to lose the car at a smaller outlying town, and to then take the train into the big city. Unless one is headed directly to the airport, in which case it's easy, but missing Rome would be a shame. No, make that a damn shame.
Regarding B&B's and agriturismos -- when not in the larger cities, they are IMO absolutely the way to go. It's easy to find them, and it's easy to find reviews and references. Again, and by way of example,
One notes that the key dates seem to be in their low season.
Google Earth is very useful in building trips, and in finding interesting destinations, and interesting roads to ride.
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From: pbridge130(AT)aol.com Subject: Re: [CR] L'Eroica: I want to go; advice on hotel, etc.
Depends on what else you would like to do while in Italy. (There are other things to do, and other places to go.) In my experience, most of the favorably-priced flights serving the immediate region will go into Pisa. Without much ado, you could also go in or out of either Rome or Milan -- I would choose Rome, because I prefer Rome, and because - as I recall - it's an hour or so closer.
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. This is a favorite of mine, a bit south of Siena:
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. Europcar has typically had the best deals that I have found. Be sure you understand from your credit card company exactly how they want you to handle insurance on the rental car.
One other comment - depending on your stomach for uncertainty, you could start shopping for an air fare around August 20 or so. In my experience, fares drop sharply around then. Shop around, and check lots of websites. They do not all have the same data. sidestep, 1800flyeurope, etc. Or maybe that's not worth it. The savings will only be about 200 or 250 per ticket, based on today's price of about 1100 san - psa - san.