I can't help as much on the food front. Beer on the other hand, I'm all over. It is also worth noting that if a place you want to go to in on the Subway line it will be at most about 30 minutes from Bay where you are staying.
For beer, try:
Bar Volo (Yonge and Dundonald), half a block from Wellesley station. Great local micro selection and very cheap pints on Tuesday nights.
C'est What? (Front near Church), a couple of blocks from King or Union station. Tons of Ontario micros on tap and cask. Really good.
Beer Bistro (King near Yonge), best bet for beer and food. A little pricey but a nice collection of beers from around the world and solid food.
Against the Grain Urban Tavern (Chorus Quay), great patio next to Sugar Beach. Good bear selection and decent food but go for the nice outdoor atmosphere on the lake.
Bellwoods Brewery (Ossington between Dundas and Queen), probably Toronto's most exciting brewery. Great patio and even better beer. Take the Dundas or Queen car to Ossington then walk a couple of blocks.
In terms of food things. I always need to get a Peameal Bacon Roll from Carousel Bakery at the St Lawrence Market. I enjoyed Globe Bistro (near Broadway station) on my last visit. For Chinese there are some great options. Haven't done Dim Sum on my last few visits so I'll leave that to others but I do enjoy the northern Chinese at Traditional Chinese Bun (Dundas and Kensington). Shoto should be good. I also enjoyed the Noodle Bar if you feel that way inclined.