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To glimpse Toronto in all its modern architectural glory, start this walk in the late afternoon or just before sunset, as the neon start to flicker to life. This tour is building-heavy, so you'd better be into some hardcore masonry. Start by hopping off the 504 King streetcar on the Theatre Block at the corner of John and King Sts and walk east past the Princess of Wales Theatre and the Royal Alexandra Theatre. At Simcoe St, cross over to Roy Thomson Hall and Canada's Walk of Fame (who knew?). Continue west past the Goethe-Institut Gallery then turn right at York St, and left onto Wellington St for the Toronto Dominion Gallery of Inuit Art.
Keep on walking to Bay St, turning north toward the Design Exchange, then wander north along Canada's answer to Wall Street. As you approach Temperance St, you'll see the Canada Permanent Building on your left, another Art Deco highlight. Walk east on Queen St, then head up Yonge St to the historic Elgin & Winter Garden Theatre Centre. From here you can detour onto Shuter St toward Massey Hall then turn left at Bond St to check out St Michael's Catholic Cathedral and the Mackenzie House, which is said to be haunted. If you cut through the garden walkway into a parking lot and look up, you'll see the mural on the south facade of the Senator Restaurant.
At the sidewalk, turn right and walk by Top O' the Senator and circle around Dundas Square to the west side of Yonge St. Walk south and pass through Eaton Centre to Trinity Square, where you'll find the Church of the Holy Trinity and its outdoor labyrinth. Cross over Bay St to City Hall and Nathan Phillips Square. From here, it's just a short streetcar ride to Clubland in the Entertainment District where you can revisit the architectural wonders of the day via a martini haze.
A Top Day in Toronto
The perfect day in Toronto begins over a big breakfast and a bottomless cup of coffee at Fran's on College St, one of the city's most enduring 24-hour diners. Amidst the bustle of early morning I watch heaving subway stations exhale long breaths of commuters and tourists and inhale those stumbling home after a big night.
If it's a sunny day I'll meet up with friends and head to the Toronto Islands - a refuge of natural beauty miles away from the city's dominating skyline. If I tire of feeding the ducks and paddling around the pond in Centre Island Park I'll hop over to Algonquin Island and admire the laid-back artist colony. Wet days are best spent snaking through the bowels of PATH, a 30km (19mi) underground network of shops, atriums and food courts - the perfect antidote for rainy day blues. For lunch I'll grab a few friends to brave the Chinatown line-ups with me and we'll pile the communal, round tables high with heaps of noodles, stir-fried veggies and a plate of Peking duck. Afterwards I'll mosey on down to Queen St W and park myself at one of Lettieri's sidewalk tables to spend the early part of the afternoon sipping espresso and taking in the colourful show: a mixture of punks, goths and a smattering of skater types.
With renewed energy I'll investigate Baldwin Village, where bohos mingle with the recent influx of martini-swilling urbanites. I love to dig deeper and find the odd Southeast Asian eatery. The nearby Art Gallery of Toronto always beckons and, while I'm at it, I'll soak up old-fashioned splendor in the Grange, a Georgian manor complete with period furnishings and costumes. Dinner in Greektown is next on the itinerary and, with a mouth full of souvlaki, a swill of wine and a moment's contemplation, I could almost mistake the scene for the back streets of Thessaloniki. To finish the night in style, I'll cab it back over to Little Italy in the west end to visit one (but probably more) of the bars along College St W. And even though I've spent the day in just one city, I'll feel like my soul has been fed an international diet of food, culture and good times.
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