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Temperatures in central Italy can be unpredictable around September/October. It could be sunny and even hot or chilly and wet. So layers is the way to go. Thin cashmere tops are good because they're lightweight and pack small into a suitcase but keep you very warm. A fleece or waterproof jacket with a hood would be one of my top choices, which (although I don't like doing this) can be worn tied around the waist if the temperature creeps up. You're also going to be grateful for lightweight waterproof baseball boots or trainers, which provide good comfort for all the walking you'll be doing. I was in Naples recently and forgot my own advice regarding the footwear and I totally underestimated how much walking I'd be doing.
We have a couple of courtesy umbrellas, which we lend to customers on our day trips, but also many of the higher end hotels will loan you one for the day if you ask. For men and women those zip-off trousers that convert into shorts or vice versa are great and look pretty cool. I particularly like Craghoppers.
As part of your survival kit you might like to include mosquito repellent and after-bite since they can be quite aggressive in September.
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We hope to see you in Rome soon!