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Help with packing for last 2 weeks in Italy, please.

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Will be traveling from Venice to Florence, on to Tuscany, then Rome and finally Amalfi coast. I always overpack ......I am the "what if" packer....what if it rains, what if it's hot, what if it's I will also need several nicer outfits for some planned dinners. I have laid out black capris, khaki capris, black pants and khaki pants, a black skirt, 3 dresses ( 1 for daytime) , some short sleeved tops and some long sleeved tops. Also a light weight raincoat and two 3/4 sleeved bLouses. After doing some reading here, I am reconsidering the long sleeved tops. Opinions and advice please. Oh, and is it warm enough to swim the last part of September along the amalfi coast? I am checking a bag, if that helps.
Thank you

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