Can I Enter Italy in a valid visa and exit in another?

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Yes, this is fine, and it is indeed why the visas were issued back to back. The Schengen system does not place any importance on the identity of the visa used by a traveler to enter or exit; it's only important that a visitor have a valid visa authorizing presence in the Schengen area (unless exempted by reason of nationality or otherwise).

It's also necessary to comply with the 90/180 rule, which applies across visas. For example, if 19 September is your 90th day in the Schengen area over the previous 178 days (or fewer), then you are not permitted to remain until 20 September.

phoog 127611

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Source: stackoverflow.com

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