Toronto is a grid on a lake, and the useful thing to know is that almost everything a visitor wants sits inside a rectangle about six kilometres across, served by two subway lines and a great many streetcars.
Day one: downtown and the waterfront
Morning. St Lawrence Market — a peameal bacon sandwich at Carousel Bakery, then the aisles. Closed Mondays, and the farmers’ market in the North Building is Saturday only.
Walk west through Old Town past St James Cathedral and the Gooderham flatiron, which is the most photographed building in the city.
Midday. The CN Tower, booked online for a timed slot. The SkyWalk from Union Station is enclosed and heated, which matters between November and March.
Afternoon. The Hockey Hall of Fame is fifteen minutes away in a Victorian bank hall, and the Stanley Cup is in the middle of it. Or the Distillery District east of Old Town for forty Victorian industrial buildings and no cars.
Evening. Dinner in the Distillery, or back downtown.
Day two: museums and the west end
Morning. The ROM or the AGO — Libeskind’s crystal or Gehry’s timber gallery, and the two are argued about constantly here. Pick one; doing both properly in a day is too much.
Lunch. Kensington Market — Jamaican patties, Portuguese tarts, empanadas, all within a hundred metres.
Afternoon. West along Queen Street West — Graffiti Alley, 401 Richmond’s galleries, and on to West Queen West and Trinity Bellwoods.
Evening. Ossington Avenue or Little Italy for dinner.
Day three: the islands and the east
Morning. The Toronto Islands — take the Ward’s Island ferry rather than Centre Island, walk the boardwalk west, and get the skyline view from the southern shore, which is much better than any view from inside the city.
Buy ferry tickets online in summer; the queue is real.
Afternoon. Casa Loma and its tunnel, or the Evergreen Brick Works in the Don Valley — the second is better on a Saturday for the market.
Evening. The Danforth for Greek food, or Leslieville in the east end.
What to book ahead
The CN Tower, the island ferry in summer, and restaurants at weekends. TIFF in September requires planning months out.
If you have a fourth day
Niagara Falls — two hours by GO Transit, and the Canadian side has the view because the Horseshoe faces this way. Combine it with Niagara-on-the-Lake for the wine.
The season decides a great deal
Toronto in July and Toronto in February are different cities. See winter in Toronto — the underground PATH network exists for a reason, and in January it is the reason you can still walk around downtown.
Two days, if that is all you have
Drop day two’s museum and merge the rest: downtown and the market on the first day, the islands and Kensington on the second. You will miss the ROM or the AGO, which is a real loss but a survivable one.
Getting oriented
Toronto is laid out on a grid and the numbering runs from the lake. Yonge Street divides east from west, so 100 Queen Street West and 100 Queen Street East are two blocks apart on opposite sides of Yonge.
The subway is a U (Line 1) crossed by an east–west line (Line 2), meeting at Bloor–Yonge and St George. Almost everything below is within a few stops of one of those.
North of Bloor the city becomes residential and suburban very quickly.
What to skip
The Eaton Centre unless you want a shopping mall. The Ripley’s Aquarium is genuinely good but is a two-hour queue in summer without a timed ticket. And the Yonge–Dundas Square area, which is Toronto’s attempt at Times Square and is not one of its successes.
The one booking that matters
If you are here in September, TIFF fills the hotels and the restaurants. Either plan around it or plan for it.
If it rains
Toronto rains and snows a great deal and the city is built for it. The PATH covers downtown underground, the Eaton Centre and the major museums are all subway-connected, and the St Lawrence Market is indoors.
The one thing that genuinely does not work in bad weather is the islands — the ferry runs, but there is no shelter out there.
What Toronto is not
Worth saying plainly: Toronto is not a city of great monuments. There is no cathedral, no old town square, no imperial palace. The buildings are mostly nineteenth-century brick and twentieth-century glass.
What it has instead is neighbourhoods, and the interesting thing about the city is that you can eat your way across four continents in an afternoon on one streetcar line. Plan for that rather than for a list of sights and it works much better.