If you're into writing; the Edgar Allen Poe house. And avoid South Street at certain times of night. Olde City has some great nightlife, but is crazy expensive.
South St. has become somewhat of a disaster over the past several years. I would say:
Italian Market
Reading Terminal Market
Eastern State Penitentiary
Get a cheesesteak, doesn't really matter where. I like Tony Luke's.
Independence Hall/Washington Park area is great.
The Stoogeum (in Lower Gwynedd Township)... although its only open about once a month. The Trolley Car Diner. A Phillies game. Olde City. Any one of the vast number of museums in and around the city.
Philadelphia is hugely diverse, and you can have a top 5 tailored to anyone's interests.