Which visa should I apply for if I need at least two entries to the Schengen area?
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Double-entry visas are created exactly for itineraries like the one you describe, and is probably what you will get issued when you apply. You can always try checking the box for requesting multiple entries, but it's unlikely you will get that as a first-time traveler -- unless you have an extremely good story why you would need to make frequent and repeated visits to the Schengen area in the future.
(Be aware that since you're planning to spend the longest time in Italy, you must apply for the visa at the Italian consulate, even though you're entering and leaving through France).
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