Without a doubt, send them to 416 Snack Bar. No resos, no utensils, great vibe, great food, plenty of wine, cocktails, beer, etc. Quite a small place.
Montgomery’s and Paris Paris are also good choices.
Kensington Market is good to walk around. Plenty of great food there - Seven Lives for tacos, San Cosme for tortas, in particular. There’s a brewery and cafes and bars there also. It’s also on the edge of Chinatown.
Outdoor skating is available at City Hall. They can rent skates when they’re there. The new Bentway Skate Trail is open also, but I don’t think there’s a place to rent skates yet.
For just cocktails, scotch, bourbon, etc, Rush Lane is great. Henrietta Lane is another option, which is near the Distillery District if they are in that neighbourhood.
If there’s looking for bars to go out to, there are options on King West (which I loathe), or Ossington, which has plenty of bars and restaurants, some with live music, such as the Dakota Tavern.
The Art Gallery of Ontario and Royal Ontario Museum are alright, with my preference for the former. Ripley’s Aquarium is at the base of the CN Tower. While it’s nice, it doesn’t compare to the Shedd, IMO.
If they want to drop a lot of dime, they can go to the top of the CN Tower and look out over the city. On a clear day, you may be able to see Rochester across Lake Ontario. You can also stand on the glass floor and look straight down.
What neighbourhood are they staying in?
As for travel, if they’re flying Porter to the island airport, they can take a quick cab to downtown. If they’re flying into Pearson, however, then they should take the UPX downtown from the airport. $12CAD/person, whereas a taxi will be about $60CAD for the flat rate, plus tip.
Let me think about other options.