The 70-passenger Miss Kim Simpson takes architecture enthusiasts on a tour of Toronto’s skyline.Kurtis Chen/Kurtis Chen/Toronto Society of Architects
It’s 1995, and you’re on a boat in Toronto’s Inner Harbour. The skyline, while impressive, is clustered just to the east of the CN Tower; cone-shaped, its western edge ramps up with Mie van der Rohe’s black TD Centre towers, the cone peaks at Edward Durrel Stone’s 72-storey First Canadian Place, and then, with the help of I.M. Pei’s Commerce Court, slants downward to the east. In the foreground is the stately Royal York Hotel, tallest in the British Empire when it opened in 1929. West of the CN Tower is the Skydome; east of the skyline cone are steeples and smokestacks. Had you been on an architecture tour, it would have lasted about half an hour. And you might have wished you’d spent your money on Chicago’s River Tour instead.
“I think at that time Toronto really wasn’t appreciating its waterfront,” says Toronto Society of Architects (TSA) executive director Joël León Danis. “I think there’s been a change of mentality as we start to do the redevelopment of the eastern portion of the waterfront.”
He’s right: the tide has turned for Toronto. And it’s not just because of the sparkling new neighbourhoods and public spaces built south of the Gardiner Expressway from Yonge to Parliament streets. No, west of the CN Tower, new parks shake hands with the lake – HTO East and West; Spadina Quay Wetlands; Toronto Music Garden; and Ireland Park fronting the restored Canada Malting Silos – and tall new buildings, whether in “South Core” or clustered around the new 106-storey supertall rising at 1 Yonge St., have trampled the once-proud cone. And the city even created a new island, Villiers Island, while naturalizing the mouth of the Don River at the same time.
Toronto’s waterfront has changed, with new towers and parks and even a new island.Dave LeBlanc/The Globe and Mail
Which means the time was right to get on the water, says Mr. Danis: “Every year we would get some comments from people who had participated in our walking tours, saying, ‘We really enjoyed it, but have you heard about Chicago and its boat tours, and have you considered doing something like that?’”
It’s hard not to hear about Chicago during almost any architecture discussion in Toronto. Both Great Lakes cities, they’re about the same size, population-wise and in land area, and both enjoy works by many of the same architects. However, since Toronto’s rivers run in ravines, a river tour in Toronto would only work for dendrophiles or squirrel lovers.
The problem for the TSA, however, was a lack of expertise vis-à-vis harbourfront logistics, passenger handling, boat types and boat schedules. So, when Waterfront BIA and Waterfront Toronto approached the TSA with the idea of doing a test-run, the aquatic, architectural adventure began to take shape.
First, the TSA selected a rather interesting vessel from the Toronto Harbour Tours’ fleet, the Miss Kim Simpson, a low-slung, 70-passenger, Amsterdam-canal-style boat with more glass area than a flashy Toronto condominium tower. By mid-summer, TSA members donned their mariner’s caps, grabbed pen and paper, and took to the water. But with so much brick-and-mortar material now available, what to highlight and what to leave out?
“We didn’t want to talk about things that we talk about in our [walking] tours, things you could see better on land,” says Mr. Danis. “So, we focus on what you can see from the water, and what are the big stories of each chunk of the waterfront? For the western harbourfront, it was definitely adaptive reuse and the ability to grab these big industrial buildings [an example is Eb Zeidler’s Queen’s Quay Terminal] and transform them; with the Islands that was a whole new area [for us] … and then there’s the eastern waterfront.”
The Toronto Society of Architects conducted 11 boat tours during September and October.Kurtis Chen/Kurtis Chen/Toronto Society of Architects
While the TSA conducted 11 boat tours during September and October, but the time your humble Architourist boarded the Oct. 5 tour, they already felt like a well-oiled machine. Our guide, architect Rania Matta, expertly steered us from the establishment of York in the late-1700s and the early icehouses on the lake, to the Canada Malting Silos and their role, to when the Toronto Islands were still connected to the mainland.
About a third of the tour poked around the Islands themselves while introducing tour-goers to Ned Hanlan and, interestingly, to the Deep Lake Water Cooling System and the return of the double-crested cormorant (and the damage these birds cause to trees). Ending at the gorgeous, copper-coloured Aqualuna condo (3XN with collaborator Kirkor) and a tantalizingly close look at the sexy Cherry Street North Bridge, the tour concluded after a highly enjoyable 90 minutes.
And while the curved windows of the Miss Kim Simpson did much to contribute to that enjoyment, that the boat sits so low on the water – I felt like I was in a large canoe –added to the experience. Its relatively small size means it can approach harbour walls for detailed views rather than constant long shots, which is something Mr. Danis says they’ll add more of in 2026.
“I definitely have the ambition of how close we can get to the bridges of the Portlands,” he says with a laugh. “Part of this has been to work with the captains and with Toronto Harbour Tours. … How close you want to be to things, where do you need to go slow so you have a little bit more time to take in something [and] how do you give everyone great views?
“The most frequent feedback we got from these tours was that [people] did not think there was that much to see and talk about,” Mr. Danis finishes. “So, a lot of surprise, and a sense of pride, which was really nice to hear.”
Dear readers, my apologies for writing about something that just closed for the year. While my schedule didn’t align with writing about the first of these pilot tours, my hope is that you’ll remember to check the TSA’s website in February or March for their 2026 schedule.