Map: Old Town and the Toronto Islands

In the 19th century, Old Town was the city’s downtown center: Upper Canada’s first parliament buildings (now long destroyed) were erected here in 1793. Now just east of the city’s financial district, the area still hosts a postcard collection of historic buildings. A trot through Toronto’s past will escort you to the Toronto Islands—picturesque mini-worlds away from the pulsing financial core that provides a silvery, cinematic backdrop.

Start in the historic St. Lawrence Market neighborhood at (1) St. Lawrence Market (92 Front Street E; www.stlawrencemarket.com), located at the corner of Jarvis Street and Front Street. Built in 1803, the South Market was the city’s first city hall and now houses a fragrant cornucopia (and grazing ground) of exotic vittles: over 50 vendors hawk such savories as Québécois artisanal cheeses, fruits, honeys, breads, and glamorous proteins (sushi-grade fish; smoked arctic char; caviar).

After a fortifying wander, walk north from Front Street along Jarvis until you reach King Street, turn left and walk west to Church Street where you’ll find (2) St. James Cathedral (King and Church Streets; www.stjamescathedral.on.ca). The cathedral first opened its grand doors for services on June 19, 1853; the 328-foot-tall (100-meter-tall) spire poked out from the cityscape, guiding ships into the harbor. From King and Church, walk south on Church until you reach Front Street again and can behold the red brick (3) Flatiron Building (49 Wellington Street E). Dating back to 1892, the flatiron was built as the head office of the Gooderham and Worts distilling company. With the city’s sharp, silver corporate towers as its backdrop, the Flatiron offers a classic Louvre-and-Pyramid-style. Past-present photo opportunity: the blade-silver cityscape offering a cold contrast with the curves and color of the old world.

Continue to walk west along Front Street, past the (4) Hockey Hall of Fame (30 Yonge Street; www.hhof.com), a temple for the puck-and-blade enthusiast, and the majestic (5) Royal York Hotel (100 Front Street W; www.fairmont.com). Turn left on York Street and head south toward Lake Ontario until you reach Queen’s Quay; turn left, walk three blocks east to the foot of Bay Street, where you will find the public ferry docks behind the Westin Harbour Castle Hotel. The ferries (fee) take passengers on a blustery ride to the (6) Toronto Islands (www.toronto.ca/parks/island). There are eight islands, all linked by footbridges. (7) Ward’s Island is the most charming and stroll-happy, with its pedestrian-only streets and Snow White-style bucolic cottages. Stroll along the boardwalk, wend your way through the curling pathways, and behold the best view of the city. Plan for a sunset ferry ride back to town, when buildings and sky blush with pink.

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