5-Day Toronto Travel Itinerary

Skip the cab line at Pearson. The UP Express train runs every 15 minutes from Terminal 1 to Union Station downtown in 28 minutes flat, for 12.35 dollars one way, or 9.25 with a PRESTO card, and it beats sitting in 401 traffic during rush hour by a wide margin. A taxi covers the same route in anywhere from 25 minutes to well over an hour depending on the time of day, for triple the price.

Day 1: Downtown Exploration

Start at the CN Tower, since lines build fast after 11am. General admission runs about 43 to 45 dollars for an adult and includes the glass floor on the lower observation level at 342 metres, a genuinely unsettling experience even if you’ve talked yourself into it beforehand. Skip EdgeWalk unless money is no object; at roughly 199 dollars for a 30-minute harnessed walk around the outside of the tower, it’s a niche thrill rather than a must-do.

From there, the Royal Ontario Museum and the Art Gallery of Ontario sit close enough together to both fit into an afternoon if you move briskly, though I’d rather spend the full afternoon at just one. The ROM’s dinosaur and Bat Cave galleries edge out the AGO for anyone travelling with kids; the AGO wins for anyone who actually wants to look at art rather than walk past it. Finish the day at St. Lawrence Market, which has been named one of the world’s best food markets more than once, and get there before 2pm on a Saturday if you want a peameal bacon sandwich from Carousel Bakery without a 20-minute queue.

For dinner, Poutini’s House of Poutine does the classic dish properly and won’t run you more than 15 dollars a plate. For a base, Fairmont Royal York sits directly above Union Station and is the most convenient mid-range option in the city for anyone relying on transit; the Ritz-Carlton a few blocks over is the splurge equivalent. Toronto runs on Eastern time and the TTC day pass costs about 13.50 dollars, covering unlimited subway, streetcar and bus rides, which is worth buying the moment you plan more than two rides in a day.

Day 2: Harbourfront and the Islands

The Toronto Islands ferry leaves from the foot of Bay Street and costs around 10 dollars round trip; go for the view back at the skyline more than for the islands themselves, though Centre Island’s boardwalk is a pleasant, unhurried walk if the weather holds. Ripley’s Aquarium sits right beside the CN Tower and is worth the roughly 40 dollar adult ticket mainly for the moving walkway through the shark tank, a genuinely well-designed touch that most aquariums don’t bother with.

One correction worth making here: the Toronto Zoo is not part of a harbourfront day. It sits far out in Scarborough, close to a 45-minute drive from downtown with no direct subway connection, so pairing it with the waterfront in one day means spending more time in transit than at either. If the zoo is on your list, give it its own half day, ideally combined with the Rouge Valley trails nearby. For dinner, the Rec Room at Union Station combines a genuinely decent kitchen with bowling and arcade games, useful if you’re travelling with a mixed group who don’t all want a sit-down meal.

Day 3: Kensington Market and Chinatown

Kensington Market rewards slow wandering more than any checklist. Fika and Moonbeam are the local coffee stops that regulars actually use, both roasting their own beans, and Courage My Love remains the market’s flagship vintage shop for anyone digging for genuinely old pieces rather than curated resale. Grey Gardens, a Michelin Bib Gourmand pick for wine and small plates, is a better bet for lunch than most of the market’s tourist-facing stalls. Graffiti Alley runs along Rush Lane behind Queen Street West and changes constantly, so even a repeat visit looks different.

Chinatown sits an easy ten-minute walk east along Dundas and is worth combining with Kensington rather than treating as a separate outing; the two neighbourhoods blend at the edges. If your dates line up with mid-August, the Taste of the Danforth festival is worth the trip east to Greektown, but it’s a once-a-year event, not something you can casually stumble into any given week.

Day 4: Distillery District

The Distillery District, a cluster of restored Victorian industrial buildings turned into galleries, shops and restaurants, is car-free and best covered on foot in two or three hours. Canoe, up in the TD Bank Tower with views over the lake, is the splurge dinner of the trip at around 100 dollars a head and books out well in advance, so reserve before you land rather than on the day. For something more casual, Elm Street Cafe does a reliable brunch. If a Mirvish production is running at the Ed Mirvish or Princess of Wales theatre, buy tickets ahead online since Toronto’s theatre district sells out its bigger shows fast, particularly on weekends.

Day 5: Shopping and Wind Down

Bloor-Yorkville is Toronto’s answer to Rodeo Drive, dense with flagship stores and a noticeably older Toronto architecture in its side streets, worth a wander even without a shopping list. The CF Toronto Eaton Centre a few blocks south is the more accessible option, with over 250 stores under one glass-vaulted roof, useful on a rainy day. If your trip lands on a Thursday night before you leave, ROM Friday Night Live style after-hours events occasionally run and are worth checking the museum’s calendar for, since standard hours don’t capture the same energy.

For a final dinner, Byblos does Middle Eastern small plates that punch well above the typical hotel-district restaurant, and Cafe Boulud inside the Four Seasons is the more classically French option if you want white tablecloths on your last night. One last practical note before you fly out: build in extra time for security at Pearson during summer peak months, since wait times have run well past the standard 90-minute buffer on busy mornings.