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Might there be an argument for the eastward DVP/Gardiner approach as well? (Though that way, the skyline unveils itself more like a striptease...)

Yes, I prefer the approach taken by the Greyhound coming in from Peterborough - 401 to DVP to Richmond.

The best place to view Toronto's skyline in my opinion is this one spot on the Leslie Steet Spit where there is an old gigantic log sitting on its side. The view is framed by trees. A few weeks ago a friend an I sat on that log and watched the sun set behind the city as the lights in the towers came on and a thunderstorm rolled over the lake behind us. It was simply a magical experience.

Similarly, looking at the distant skyline from Port Credit or Bronte Harbour in the sunset when it becomes this far off collection of pink glistening spikes is pretty awe-inspiring as well.
 
coming down richmond before you hit parliament is a nice view.

heading west on unwin from leslie, at the first curve is also a nice view, especially at night.
 
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7 Jackes Avenue. It is an apartment building (The Summerhill) on the east side of Yonge, a few blocks south of St. Clair, near the crest of the upward slope of Yonge. My SO's old apartment was on the 27th floor, facing south, and the view is astonishing. You can see everything from the Ashbridge's Bay area to the east, to the CNE in the west. Pretty much every major skyscraper south of St. Clair is visible in some way or another (except Maple Leaf Square, etc.). Truly a big-city, urban view. Bonus: perhaps the only place in the city where one can see, simultaneously, Bloor trains traversing the Viaduct, Yonge trains in the open cut south of Summerhill station, and CP trains along the North Toronto sub. A visual feast all around. Huge balcony, many a cocktail party was had there. Do we ever miss that view...
 
I'd vote for the DVP-->Gardiner stretch as quite lovely.

The Islands/ferry are a bit obvious but if you can find Snake Island it's a great quiet place with a rather amazing view, framed by a quiet cove. I got a great shot from there years ago.
 
I rarely get out of town, and usually when I do I take the DVP out of the city, but this past weekend I came in from the other way at night.

I must say, I'm really starting to like the view on the Gardiner coming into the city by car from the west... Especially at night.
 
Here are my favourites.

O'conner and Victoria Park.

Broadview and Sparkhall Ave.

Also, the roof patio at Murphys Law is nice.
 
Window seats on Porter flights from Ottawa or Montreal to the Island airport give a pretty good view of downtown (and most of the eastern end of the city actually).

Probably the best view would be in the right-hand (D) window seats as you land from east to west. I'm not sure you get as good a view taking off. If you are landing from west to east, they fly out over the lake and circle around by Ontario Place, so not as good a view.

It's a pretty nice view from the the airport ferry too.
 
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The Islands/ferry are a bit obvious but if you can find Snake Island it's a great quiet place with a rather amazing view, framed by a quiet cove. I got a great shot from there years ago.


Which one's Snake Island? Is that the tiny one with the footbridge W of Algonquin?

Actually, I find the ferry/Islands view the most anticlimactic, at least wherever Harbour Square hogs the front and blocks out everything behind...
 
Maybe not the best place to view Toronto's skyline, but it's always surprising to see the skyline on the QEW from as far away as the Burlington Skyway and even the Garden City Skyway in St. Catharines.
 
I think any of those spots where the CN Tower cluster just "materializes"--from the 401, the 404, Airport Road etc--ought to qualify.
 
The Hilton has a glass elevator that goes up 32 floors, some great views of queen st w and the lake from the top floor.
 

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