Luggage And Bags: pack an extra duffle/gym/tote bag for trinkets and souvenirs.
A shoulder type bag to carry your camera, books, maps, a smaller purse.
Clothing/Shoes/Weather Gear: Vatican dress code requires all those entering St. Peter's to be modestly dressed. Shoulders must be covered. No shorts are allowed for men or women. Men must wear long pants and women choosing to wear skirts must have the length to the knee at minimum.
Bring a light jacket/umbrella in case of rain, but temperatures do reach into the 80s in late May.
When touring around the rest of Rome. dress comfortably....spring dresses, shorts, capri pants, skirts, linen pants, t-shirts are all good recommendations for tours in Rome. The Romans are quite fashionable, you will stick out less as a tourist if you dress well and sensibly.
Bring something nice for a evening out. Comfortable shoes for walking. I did manage to walk around Rome in heels for a few hours but be careful around cobblestones as they the heel sometimes will get stuck.
Toiletries & Medical Supplies: Band-aids, prescription medication and prescription if in need of refills, contact lens cleaners/solutions, extra contact lens case, pain medication (ibuprofen, aspirin, etc....you will be paying a lot more for them in the pharmacies in Rome).
Antibacterial hand wipes/gels for those moments when you just can't get to wash your hands.
Photo Equipment: Have a big enough card if you have a digital camera and extra batteries (you might have to pay more in Rome if it is a specialty battery)
Extra film for 35 mm point and shoot/SLR cameras.
Miscellaneous: SUNGLASSES!!!! Your eyes will thank you. (If you forget them, treat yourself to a nice Italian pair, just not those fake ones they sell on the street).
Money belt or money pocket when in more sketchy areas of Rome (Termini Station)
Journal to write down all the great places you visited throughout your trip.
Chewing gum/breath mints to neutralize all that garlic ;-)
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