You can find all kinds of unique shops along (and just off) South Street. From Fashion (new and second-hand) and Art (crafts and unique items for house decor, etc) to Sex Shops and Music. Some bars and restaurants thrown in between too!
Begin your day right with an Irish Breakfast and/or Irish Coffee at Downey's at Front and South, continue (west) on South Street to find various shops (Zipperhead, Tower Records, etc). Stop for a slice of Lorenzo's pizza for lunch and then a Rita's water ice for dessert or an Irish Coffee at Downey's at Front and South. Top off the afternoon with a Stella or Guinness at the Dark Horse (Dicken's Inn) at 2nd near Lombard on Head House Square. For dinner had over to Django (BYOB) or the Latest Dish. Fluid night club is over the Latest Dish.
What to buy: Whatever tickles your fancy!
South Street is quite a unique street, kind of forming the South border of Philadelphia City Center. You find an abundance of shops there, ranging from a very good Italian supermarket (fabulous bread) over a wonderful shop for used books (every sorted well in categories, large selection, two floors, reasonable prices) and an arts and crafts shop to tattoo parlors and shops for more unsual equipment, jewelry or home decoration items. The clientele is just as diverse and interesting as the shops and almost everyone will fine something to buy there (I unfortunately always find several things...)
What to buy: As mentioned above: South Street gives you Italian food, tattoos and piercings, different hats, used books, crafts supply, old furniture, second hand clothes, jewelry, stationary and greeting cards - everything from the ordinary to the highly unusual.
What to pay: Most shops on South Street are in a moderate price range, so it is a good place to make bargains.