Where to start?
Art: Visit the
Art Gallery of Ontario (AGO). The building was just made over by Frank Geary. You can also see the Ontario College of Art and Design Building
There, you are steps from Queen West, which you will find has some cool shops including the Silver Snail (Toronto's best comic book store). There are a number of pubs along that stretch as well.
I would also suggest heading to Kensington Market, there are some great shops, vintage clothing stores, coffee houses and just plain cool atmosphere.
I would also recommend wandering through Chinatown.
Thankfully, all of these activities are in the same area! (See map) The AGO is on Dundas with Chinatown and Kensington just west... the Silver Snail and Queen Street are just south of the AGO and west on Queen are some great restaurants (try Swan for their Grilled Cheese - trust me).
Toronto - stuff - Google Maps