At FoundLocally, we consider "Toronto" as roughly the old "City of Toronto", between the Humber River (and Etobicoke) on the west and Victoria Park (and Scarborough) on the east, and below Eglinton Ave (and North York) to the north, though the actual political boundary zig-zagged a fair bit
Further afield, beyond roday's municipal boundaries are Oshawa-Durham to the east of city limits, York Region to the north of the city limits, and Mississauga & Brampton) west of the city lLmits.
Here are our picks for the must-see attractions in downtown Toronto, taking a walking tour that covers the territory in a clockwise direction:
Starting at the New City Hall, now over 40 years old, you see Nathan Phillips Square in front of you, Osgoode Hall (law courts) to the west and the century-old Old City Hill to the east.
Head a block east to hit Eatonís Centre, once Canada's largest shopping mall, and still a shopping and visual spectacular. There is a large Bay store to the south of the mall, but exit the north end (by H&M) for this tour
Across Yonge Street is Dundas Square a popular location for various festivals and live concerts.
Yonge Street is Canada's most popular shopping street, and is the world's longest street, heading north turning to highway 1 to North Bay and then arcing west to Thunder Bay a distance of over 1900 kilometres. Checkout the stores a few blocks north, and then head back south past the Eaton Centre.
There are a number of historical theatres on Yonge, including Massey Hall and the Elgin & Winter Garden Theatres, or just to the west in the Theatre District along King St, including the famous Roy Thomson Hall
South of Richmond is a cluster of office towers which form the Financial District, the headquarters of Canada's major banks, law firms, stock brokers, and many public companies. The old Toronto Stock Exchange building is now the Design Exchange Museum. The art deco CIBC Tower used to be the tallest building in the British Empire. The gleaming white First Canadian Centre is headquarters for BMO Bank of Montreal. The gold glass building is headquarters for the Royal Bank of Canada. All are connected by a vast undergound PATH system, that runs from Union Station north to the Eaton Centre, and connected with subway stations along the way.
At the foot of Yonge (at Front) is BCE Place (look inside!) and the Hockey Hall of Fame (a perfect rest stop for hockey fans).
Head west along front to pass Union Station (VIA Rail and GO Train station) and the historic Royal York hotel across the street.
Follow University Avenue to the right and King Street and the heart of Toronto's Theatre District, The Royal Alex, the Pearl, and Roy Thomson Hall, as well as Canada's Walk of Fame (modeled after Hollywood's)
On John Street you can head north to CHUM City, home of MuchMusic and all their "VJ" antics, or you can had south past CBC's national headquarters (the building looks like its gift-wrapped in red ribbon)
Across Front Street is the CN Tower, for 30 years the world's tallest free standing structure, worth the elevator ride up (bring binoculars-if the weatherís fine and the root is open on the Rogers Center/Skydome, you can watch the baseball or football game for free, through the glass floor!)
If you survived Day One, your second day should be spent more uptown.
Head four blocks west of University Avenue to McCaul Street and north a bit to OCAD University (formerly Ontario College of Art & Design) with its unique campus building design, and beside it is the Art Gallery of Ontario, which is home to many major travelling exhibitions as well as its own.
Head back east on Dundas to the campus University of Toronto is on the west side of University Ave, and worth a short walk to explore the old and the new architecture of the buildings.
FYI: If you want to explore the ethnically interesting Kensington Market area of Toronto, its just a few blocks to the west, along and west of Spadina, between Dundas and College. For some, it may be more interesting than exploring U of T.
Continue north on University to Queen's Park, the Ontario Legislature, on a pretty oval in the middle of University Avenue. There are several hospitals to the south of Queens Park
At Bloor Street and University is the Royal Ontario Museum, which recently received a "Crystal" makeover by architect Michael Libeskind, and home to a collection of 3 million artifacts.
Along Bloor Street is Canada's best high-end shopping including the Holt Renfrew flagships tore, and many world class designer boutiques and chi-chi restaurants. There is also the Bata Shoe Museum
North of Bloor is Yorkville, once headquarters of the 1960s anti-war hippie movement, now headquarters of the high-end "retail therapy" practitioners, plastic surgeons, and the many visiting Hollywood celebrities.
Head 4 blocks north to Davenport Rd (just up the hil from Bloor street), and then east a few more to Casa Loma, and house that looks like a castle built a century ago by a wealthy businessman, who had to sell it when his fortunes turned. Its been a public museum & venue ever since.
Head back south to Bloor Street and head west to Bathurst to Mirvish Village also has lots of theatres, shops and restaurants, which might be a good end-of-day stop after detouring to the next attraction
There is so much to see west of Toronto's downtown
Start at and The Island Ferry Terminal (this side-trip to the islands, the beaches, and the other attractions on any one of three ferries, is worth at least half a day) and head west to adjoining Harbour Square Park, the site of many waterfront festivals.
Head west along either the Waterfront Trail, or along Queens Quay W to pass several waterfront condo buildings, marinas and moorings, the Amsterdam Brewhouse and you'll see on the west end of the Island the Billy Bishop Island Airport
Head away from the water on Bathurst and underneath the Gardiner Expressway to get to Old Fort York (the entrance is 300m west on Old Fort York Rd) which was the site of an important battle in the War of 1812. At that time, Fort York was on the waterfront, and protected the harbour.
To the west is the Canadian National Exhibition (CNE) which hosts Canada's biggest summer fair the last two weeks of august. Over the year many trade fairs, cultural events, and sporting competitions are held at CNE facilities.
Just across Lake Shore Boulevard is Ontario Place which is home to the Budweiser Stage, Echo Beach, a waterslide park, the Cinesphere (the world's first IMAX theatre) and a marina.
You can continue west along Lakeshore Boulevard. You will see a breakwater protecting the shore, and pass ,strong>The Boulevard Club and marina and get to Sunnyside Pool and the Sunnyside Pavilion.
Head north of Parkside Dr underneath the Gardiner Expressway and "voila!" you are at the end of High Park, which is Toronto's largest park, much of it is forested, but it also has and has the High Park Zoo, the High park outdoor pool, a playground, and Grenadier Pond.
On its northern end is Bloor Street, and he commercial strip is called "Bloor Street West" and has the Bloor subway line that can take you back to city centre quickly.
We recommend (time permitting) go just a few blocks east of Keele (High Park's eastern boundary) is Roncesvalles a trendy shopping district, you can take south to Queen Street.
There you can catch a streetcar east into the Queen Street West shopping district
East of downtown are many attractions, including the vast Don Valley.
Start at Union Station at the foot on Yonge Street and head east on Front Street.
You will pass the Sony Centre For Performing Arts venue, and a block up Yonge Street is the Hockey Hall of Fame, and block east is the St Lawrence Centre for the Arts, and on the north side of the street is the triangular-shaped Flatiron Building.
Another block east and you reach St Lawrence Market which has been running a farmers market since 1803 (yes, eighteen-oh-three).
Head south from here and east along The Explanade (a shopping & nightlife district) and you'll soon reach the Distillery Historical District, once the Gooderham-Worts Distillery, the largest distillery complex in the British Empire. its now home to the Mill Street Brewery, and the Young Centre for the Performing Arts.
A few blocks east, on the Don River, is the Corktown Common park. There is a GO-Transit railway siding (parking lot) on the south side of the train tracks.
From here there are several directions of interest you can take:
These attractions are worth a short detour if you are in the area., and worth a half to a full day each.