Philly is really fun, for about a day (or two)...
South Street is sorta like Queen, so it's nifty. But stay between Front and Sixth Streets...
On Friday, I'd hit Penn's Landing, on the riverfront, basically because there won't be any weekend crowds. It's not the most exiting thing in the world, but, believe me, the more you have to do while in town, the better.
You can cross right over to Market Street from Penn's Landing, and from there you could walk up until City Hall. City Hall's the big building down the street with William Penn at the top. Btw, that statue used to be the marker for the highest allowed building height in the city.
On the way to city hall you'll go by the liberty bell and congress hall (at 5th). Some people feel these are worth checking out. I lived there most of my life, and never went into congress hall...
When you get to city hall, there are a few choices. You can walk south to Walnut, then west a few blocks and hit the fashionable Rittenhouse Square. The only interesting thing I remember there is a famous croissant shop owned by a bunch of french people.
You can also head N.West, up the ben franklin parkway, to some of the museums. The only one really worth checking out is the Museum of art. It's the gigantic place at the end of the parkway. It's free on Sunday mornings!!!
If youre driving around, head up I95 to New Hope, a cool little town that looks like it was built by colonial hippies.
Ok, some food tips. You didn't mention your budget...
South Street Souvlaki is great for Greek, and its cheap. It's on... South Street, somewhere around the corner of 4th.
Roman Bistro is just off 2nd at headhouse square. It's italian and prices are "family restaurantish."
Just off 2nd and Chestnut (on 2nd) is a sandwich shop called Larry's. It's Great! Get and Italian Hoagie! Mail me one, too.
There's an IHOP on Walnut near Rittenhouse Square...
Ok, this one may be a chain, but I've never seen one in Toronto, so: on South, near the corner of 5th, is Cool Peppers. This is the best mexican junk food I've ever had. Their salsa bar is incredible.
For good indian, there's a place called Samosa just east of Broad (uhh, they changed "Broad" to "Avenue of the Arts").
What kind of night spots do you like?
If I think of anything else, I'll post...
Good luck...
Charles