Check the weather forecast. Italy in May is generally warm and great for being outdoors. Expect the northern areas, like Lombardy, to average in the mid-70s in May, and the middle of the country, around Lazio, and the southern regions, such as Calabria, to average in the upper 70s and low 80s. Get more detailed average temperatures with a regional map (see Resources). Get current conditions from the Weather Channel (see Resources).
Start with the shoes. Bring comfortable, breathable shoes that won't make your feet sweat. Make sure the shoes are broken in and good for walking.
Pack the tops and bottoms. Capris, casual skirts and slacks are ideal bottoms. Keep them comfortable, loose-fitting and easily washable. Pack short-sleeves or tank tops and a couple of longer-sleeved layers. Bring a lightweight jacket for rain or chill.
Bring a hat. Wider-brimmed hats made of a lightweight, rainproof material will be a godsend for keeping the sun out of your face or the rain off your head.
Take a scarf or two. Longer silk scarves will add some pizazz to a mundane look as well as keep you cozy if the weather turns a bit chilly.
Include at least one dressier outfit. Days may be spent tromping over cobblestones, but you want to make sure to bring a nicer ensemble for a night out on the town. It doesn't matter if you wear the same dressier outfit every time you go out. Nobody is going to notice, and nobody is going to care.
Remember your socks and underwear.
