[Effendi]

Wind has no special plans for the i-phone, since it's the only operator in Italy which is not selling it. But it has several interesting data options that you saw on the sticky thread.
With TIM you have the Maxxi Internet 10 option with 50 MB/day, but it's a wap APN, so with some limitations, AFAIK. Similar option is available on 3, with no limitations, but only using their 3G network which could be non existant in the Chianti area.

Vodafone has a special iphone option called "Mobile Internet per iPhone" at 3€/week including 500MB/week.

Coverage in Rome and Florence is fine with all operators, in the Chianti probably TIM and Wind could be the best options, just check the coverage pages.

In any case, you just have to buy a normal prepaid card with no options, refill it and then ask to activate the data option you chose.
Prices for international calls are usually quite high. With Wind you have the Call Your Country option (30c/min), with TIM the Welcome Home plan (same rate).