Where to stay downtown? (high school, university, live)

[LaFemme86]

Hi all,

I'm visiting Toronto in early August for a few days. I'm mainly staying with family in Oakville, but wanted to get an Airbnb for the Friday and Saturday night with my boyfriend, as we have something to attend both nights downtown.

I lived in Canada for 9 years, Mississauga for high school and then downtown Toronto in the Fort York area from 2005-2009 (for university), but don't really know the best areas to stay anymore. When I've visited over the years, I've done everything from the new areas in Ossington to Kensington Market to the Beaches to King West/ Liberty Village to the Danforth and so on... all based on what my friends were regularly doing at the time. I have absolutely no idea where the best place to be is anymore.

We're in our late 20s, coming from NYC. He's born and bred NYC and has only been to Toronto a handful of times with me. I want to stay in a nicer area with enough stuff somewhat walkable for daytime things. We have an event both nights around the Ex area, which will likely go till 10-11 PM, but I don't necessarily want to stay near there-- would prefer to be where we can see/ do more.

Any suggestions? There's a ton of places but so much has changed since I've lived there that I want to choose the right area.

Also-- the Friday night, we do have dinner open-- any suggestions? We are big foodies and eat absolutely anything. And for both nights, after our event, what areas do you recommend if we're looking for a bar type atmosphere, maybe patio/ live music or something of the sort?

TIA!