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Usually, in October, southern Italy (like Amalfi, Pompei) is good weather, some kind of summer (but daylight is shorter, and sun goes down earlier)
Anyway, weather in october can be odd, but every year it's a different thing... if you want to take the "risk", in october, there is very less turists, expecially less internal tourists (italians)... so, it can be more peaceful, and pretty nice... even if, the most-must-see places are crowded 365 days... i mean, Venice, Colosseo (Rome), San Pietro (Rome), Firenze...
it's up to you... personally, i usually spend the summer in the mountains, and i tour the cities in fall/spring... i really hate crowded places.
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