It's long been known as one of the safest metropolises in the world—(but its thrilling new architecture, by the best of today's big names, flirts with danger. (Here, the shock of the new comes in steel and glass

VIDEO: Explore Toronto's architecture scene with Condé Nast Traveler's Kate Maxwell.

THE SCOOP
Peter Ustinov once quipped that Toronto is New York run by the Swiss. It was meant as a compliment, but Canada's largest city seems to be on a mission to shrug off its staid reputation by giving itself an architectural makeover. The latest addition may well be the best: Frank Gehry's makeover of the Art Gallery of Ontario (AGO), his first commission in the city of his birth. Don't look for the over-the-top flights of architectural fancy Gehry made famous with Los Angeles's Disney Concert Hall; AGO is being heralded as a return to his subtler style of yore—although for Gehry, subtle means a glass facade that looks like a billowing sail and a spiral staircase that resembles a corkscrew rendered in pasta (877-225-4246; ago.net).

If it's daring whimsy you seek, check out Will Alsop's Sharp Centre for Design, at the Ontario College of Art and Design. A 270-foot-long rectangular slab hoisted 85 feet off the ground, it's supported by slanted legs that (appropriately) bring to mind colored pencils. Finished in 2004, the Tabletop, as locals call it, kicked off Toronto's architectural renaissance and was at first considered lovably outlandish (416-977-6000; ocad.ca). But that was before Daniel Libeskind's addition to the Royal Ontario Museum redefined Torontonians' idea of outlandish. His Michael Lee-Chin Crystal wing is jutting, knife sharp, geometric, and yet somehow reminiscent of an iceberg—in short, it ain't your grandmother's gallery (although the stone Victorian edifice it's attached to definitely is). The design inspires love and hate, and not much in between. But regardless of what you think of the new wing, the exhibits inside—collections include dinosaur skeletons and Japanese ceramics—are worth the $18 admission (416-586-8000; rom.on.ca).

Critics accused native Torontonian Jack Diamond of playing it safe when the Four Seasons Centre for the Performing Arts opened in 2006. Since then, the opera house's understated elegance has been winning the hearts of skeptics and architecture critics alike. The Canadian Opera Company and the National Ballet of Canada perform here, so if all you do is admire it from the street, you'll miss what may be the best acoustics on the continent. Think of it as architecture you can hear (416-363-8231; coc.ca).

THE CHEAP THRILL
Head to the CN Tower—a 1970s standout—and take the glass-bottom elevator more than a thousand feet up to the Look Out; then change elevators and zoom up to the 1,465-foot Sky Pod for a view across Lake Ontario, all the way to Rochester (cntower.ca; $17).