Exterior of Art Gallery of Ontario (AGO), Toronto, Canada

Art Gallery of Ontario (AGO)

Architecture buffs won't want to miss Frank Gehry's transformed AGO with its iconic Douglas fir-hewn spiral staircase. The $276-million redesign of the historic gallery, completed in 2008, was the Toronto native's first-ever project in Canada. AGO houses the world's largest Canadian art collection, from early 20th-century wilderness landscapes by the Group of Seven to contemporary Inuit sculptures, as well as a polished museum restaurant offering exhibit-inspired tasting menus.

Aerial View - CN Tower,Toronto, Canada - Courtesy Toursim Toronto

CN Tower

When completed in 1976, the Toronto skyline's quirky centerpiece was the tallest freestanding structure on earth. Though this title was surrendered to the Burj Khalifa in 2010 (the CN Tower still claims the Western Hemisphere), the panoramic views from 1,815 feet continue to draw some two million visitors to the observation deck every year. On clear days, kids will love soaring above the cityscape in glass-walled elevators and squinting across Lake Ontario to glimpse the vapor rising above Niagara Falls.

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Exterior View - Distillery District,Toronto, Canada

Distillery District

During its heyday in the 19th century, Gooderham and Worts was the largest whisky distillery in the world. After shuttering for good in 1990, the 13-acre Victorian landmark lay abandoned for nearly a decade, until civic-minded developers proposed a plan for its restoration. The revitalized district reopened in 2003 as a mixed-use pedestrian "village," its industrial buildings newly occupied by independent boutiques, galleries and culinary artisans. The former cannery, reenvisioned as a creative incubator, now serves as studio and performance space for a community of emerging artists and designers. The neighborhood's wide, red brick lanes are ideal for an urban ramble. Be sure to stop into Hoi Bo, whose waxed canvas totes and simple linen dresses are handmade on-site, and book a tasting at Ontario Spring Water Sake (the only producer of locally brewed, unpasteurized sake in eastern North America). The legendary SOMA Chocolatemaker is also a must for hot cocoa and Douglas fir truffles.

Iterior View - St. Lawrence Market,Toronto, Canada

St. Lawrence Market

Its open-plan canopied interior was modeled directly on London's Victoria Station, but if you know where to look inside today's market, you can still see traces of Toronto's original city hall, most of which was swallowed during the market's reconstruction at the turn of the 20th century (ask a merchant to point out the 19th-century façade and even the old prison). When the new market opened in 1904, before the rise of commercial refrigeration, the slightly angled floor served to facilitate cleanup after a day of live animal processing, making it easier to sweep away the grime. Today, in addition to butchers and fishmongers, you'll find purveyors of everything from old-fashioned bagels to new-wave juice cleanses. Be sure to have the famed peameal bacon sandwich at Carousel Bakery, sample some of the 38 varieties of mustard available at Kozlik's and taste ice wines from nearby town Niagara-on-the-Lake.

Exterior View - TIFF Bell Lightbox,Toronto, Canada - Courtesy Charles Leonio, Wire Image Getty for TIFF

TIFF Bell Lightbox

It may be at its buzziest in September, but the Toronto International Film Festival's official home is always a festive place to catch a flick, whether it’s a new release or a throwback from the library's extensive archive. Limited-release indie and documentary films are shown throughout the year, often in conjunction with director-led Q&A's. TIFF regularly hosts traveling exhibits celebrating the work of influential filmmakers and runs hands-on workshops for children on subjects like animation and video game design.

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