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If you're traveling between Easter and October, it's always good to pack with layering in mind: it can be very cool in the morning, and then heat up during the course of the day. Murderously hot weather, especially in July and August, calls for breathable fabrics. If you visit in November, pack rain gear, as it seems that all the rain that didn't happen in the summer happens then. Winters in most parts of Tuscany and Umbria are not particularly cold, but there are exceptions. Pack your fleece.
You can get aspirin and the like over the counter, but it does often mean waiting in long pharmacy lines. It's best to bring aspirin and other medicine with you. It's always wise to travel with tissues, as very often public toilets are not equipped with basic necessities. If you rent a car, be particularly vigilant when making a bathroom or food break: don't leave unattended luggage in the front or back seat of the car—thieves recognize rental cars, and often target them for smash-and-grabs.
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