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How far in advance should I reserve car rental and other car related questions?

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Now the car questions.

How far in advance should I reserve a car?

One HUGE problem I see is that automatics are more expensive. I haven't driven a stick shift in years and my 79 year old father, g-d bless him, is awful in an automatic as it is. Not sure about my mother. Dad really wants automatic. I have done searches and the cars are not like they are here in the US. They are smaller. We pretty much need a 4 door as my dad is a bit portly and it is not a pretty sight watching him maneuver in and out of a 2 door into and out of a back seat. (Even the front seat is a problem.)

What type of car would be best? Obviously not a compact and I don't think there are too many compact automatics in Italy.

Also, (here we go again), what SHOULD I expect to pay? (10 days or so).

Eager to hear.

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