Perugia, Italy sounds wonderful! You probably have already considered all of the following but just in case... I also pack protein bars, dried raisins and coffee in my one-bag (like Jean, I get migraines if I skip coffee) Many European hotel rooms don't have coffee machines and if available they often don't provide packets for more than one cup per person (an immersion heater for me is always a more valued travel item than a curling iron), I bring cough drops as they don't have to go in the "liquids" bag and, naturally, some over-the-counter meds for various ailments that may crop up during travel. For allergy suffers, the face masks we saw so much of during Covid are helpful--especially when folks think if a bit of perfume and aftershave are good, more must be better! In these times, I'd pack some masks just in case mandates changed.
Bring travel-sized hand sanitizer on the plane. I preload books on my Kindle and a movie or two (hard on the battery life but wonderful when feeling stuck and down in the dumps).
In a travel risk management plan, I tend to lean towards over-thinking or over-planning every single time. (We've lived in France, Germany, the USA and Canada and travelled a fair bit abroad). I'd make sure to provide authorization for someone I trust to make medical and financial decisions if I were unable to. We usually check government websites for health, security and geopolitical risks; we try to have cursory understanding of the country's culture, language and any relevant legal considerations--particularly as they pertain to Covid, where to get the antigen or other testing, and recommended health insurance coverage. We try to check in advance how to access emergency services. We bring a copy (and leave a list with family at home) of emergency contacts, a copy of our passports and, if applicable, visas, health insurance information, prescriptions, ticket numbers, itinerary (including stopovers, lodgings, etc), nowadays that includes a copy of proof of Covid vaccination. You may want to identify how you would get to your place of quarantine (here we'd take a taxi or a private car and are required to wear/change to a new mask during transit.) Unfortunately, dealing with border officials and local security is not a one-size-fits-all experience especially as things evolve.
But what a wonderful experience you will have! Wishing you all the best on your trip.