ohh my god is there a patio better than Pregos in the city? answer is, ofcourse, no.
I don't think any other place is Toronto has such a sweet patio. Its right at the most famous intersection of bloor and avenue in yorkville yet tucked besides the church saving it from the busy traffic. Greatest patio for star gazing and people watching.
it's at the best corner of Toronto!! Right on Queen street. The corner is always full of trendy, happy people! The food is good, and the beer is always cold!! Great service!

The rooftop patio has a great view, is in Yorkville but not a snobbish crowd. Sometimes you see MTV staff there. The food is alright and the prices are low for the area. Good vibes! The picture is of the sky one night from the Pilot rooftop.
you can really critique the ROM crystal from a good angle.
Parkdale has plenty of patios but the Caddy remains one of my faves. It's big, airy and full of friendly people. While not immune from intense westward gentrification, the Caddy is definitely not just a snooty hipster hangout.
Decent daily specials (try the fish and chips!) are on offer along with an extensive menu of classic bar food standbys.
it's a bit secluded, pretty spacious and you can have a conversation without yelling to be heard.
A new found fav from summer '06! Easy to get to, there is parking for those who care to drive when the sun is shining and there are cool beers to be had, and great pub eats!
something about the only color that is used for decor being white makes the patio amazing.... as well the crowd... always a good night.