Do I need an automatic transmission, and how do I book one?

If you can't drive a stick confidently on a hill start, book an automatic — and book it early, because they're a minority of the Italian fleet and sell out months ahead in high season. They cost meaningfully more and the category you reserve may be larger than you want, which matters on narrow roads. Reserve directly with a company that guarantees transmission type rather than through a broker whose "or similar" can mean manual. Confirm at pickup before signing. Learning to drive manual on a Tuscan hill town street with a queue behind you is not the holiday memory you're after.