Interesting things to do at Philly, NY, and Canada?

In Canada - go to Niagara and take a ride on the "Maid of the Mist" (the boat that goes right up to the falls). It's an amazing experience.

Canada is quite the big place. What province will you be in?

Shopping and eating, If it wasnt for my girlfriend thats all I would do...lol

In New York, I would recommend that you take a trip in the double decker bus in Manhattan that allows you to get on and off at various stops. There is a tour guide that describes various spots like Times Square (the cross roads of the world), the Empire State Building, Madison Square Garden, the former World Trade Center site, City Hall, the Intrepid Air and Space Museum, etc. Start early. There are also numerous restaurants serving every conceivable cuisine imaginable. Take a ride in a horse drawn carriage in Central Park. Visit the various night clubs / comedy clubs, or if lucky attempt to obtain "free" tickets to see David Letterman. Take a ride on the Circle Line and see Manhattan and the Statue of Liberty from the water. There is so much to do and usually not enough time to do it in. Enjoy your stay.

At the same time ?

Ummm, do you have any idea how big Canada is?? What province will you be visiting??

I've never been to Philly but I just got back from NY, and I'd say the coolest thing I did was walk the Brooklyn Bridge and take the State Island Ferry (both free). Canada was actually my favorite vacation ever, and I visited Banf National Park. Sunning, honestly. Here's a webcam so you can see it for yourself: http://www.explorerockies.com/banff-webcam/