You want comfortable, well fitting flat shoes. No heels for day travel, but maybe one pair for night time dinning or dancing. Your shoes should be broken in because new shoes can cause blisters while walking up the many stairs and hills you will encounter. A small pair of sandals can also be easily packed if you are planning a beach visit.
Sweaters are bulky, but necessary on cold nights, so just bring one. A light weight jacket is ideal, especially wind breakers which pack nicely and and can be rolled up to be wrinkle free. A hooded sweat shirt can be substituted for a sweater.
Light weight material pants are recommended instead of shorts. T-shirts are acceptable for warmer days. Blue jeans are a good choice for rainy climates and night travel. Bring enough socks and undergarments for five days. You should wear a concealed wallet around your neck or a money belt to keep your passport, credit cards and local currency. This will keep your things safe from being lost or stolen.