
words :: Dan Rubinstein.
Toronto’s Leslie Street Spit is a busy place on a blue-sky weekday morning in June. Hundreds of double-crested cormorants swoop through the air and roost on the denuded trees of the landfill turned nature refuge that juts into Lake Ontario just east of the downtown core. Below me, dozens of common carp huddle in the murky shallows of a small lagoon. The five-kilometre headland, a still-growing repository for construction debris, is closed to pedestrian and cyclist visitors during business hours. But there are no restrictions on approaching by water, so a friend and I pumped up our inflatable stand-up paddleboards at Cherry Beach and made the 15-minute crossing. Now we’re surrounded by the sights and sounds of cormorants and carp, seagulls and swans. To the northwest, across the inner harbour, loom the CN Tower and the glassy sundrenched skyline of Canada’s biggest city.

SUP Toronto: Lake Ontario’s Urban Face
Despite growing up in Toronto and spending my first two decades here, I have never seen this view before. Because I have never paddled in my hometown before. But four years of an intensifying obsession with SUP—hitting the water from British Columbia to Newfoundland and a handful of provinces in between—I’ve made the familiar drive down Highway 401 from Ottawa to deepen my relationship with Lake Ontario’s urban face. One of the things I love most about paddleboarding is how easy it is to get onto the water. Another is the feeling of defiance. We leave behind the Spit’s sheltered shoreline and head into the wind toward the Tower, surfing the wake kicked up by police boats and aiming for the canals that cut through the Toronto Islands. Amidst a couple million other souls confined to dry land, this entire waterscape is our carefree and car-free playground.

The route we’re paddling—a figure eight from Cherry Beach to the Spit to the Islands, with a short portage to the open Lake Ontario side for the return leg—was suggested to me by Antonio Lennert, the founder and CEO (Chief Experience Officer) of Surf the Greats.
Surf (and SUP) the Greats
A Brazilian surfer who moved to Toronto in 2008, Lennert was surprised by how few people he saw on and in the water when he cycled and ran along the city’s beaches. Knowing that Lake Ontario was no longer as polluted as it had been, he began to canoe and kayak, then realized that you don’t need an ocean to catch swells. But the waves were inconsistent, so about five years ago Lennert got into paddleboarding, which he had tried during a trip back home. At the same time, organizations such as Swim Drink Fish were helping to increase water quality awareness, and the local scene was growing. All of this crystallized into Surf the Greats, which started as a jokey Instagram hashtag and has evolved into a thriving SUP and surf shop that offers lessons, rentals and repairs and, with its storefront in the Leslieville neighbourhood, serves as a hub for the city’s waterborne community.
SUP is so simple. It’s the optimal human-powered watercraft. You can do it entirely on your own terms…
“It was a passion project at first,” says Lennert, who got certified as a SUP and surf coach before opening Surf the Greats in 2014. “I wanted to create a community where I could belong—so I could stay here. Canada has such a long history of paddling, and SUP has so much potential. There’s a learning curve, and education and safety are important, but in a big city like Toronto, the sport can be incredibly liberating. You can get away from all the people and noise and get a new perspective. Once you get somebody standing on a board and paddling and feeling comfortable, their relationship with the lake changes. If they start paddling regularly, it can change their life.” Surf the Greats has stayed true to Lennert’s eco-mindset by hosting beach cleanups and holds workshops on everything from wave forecasting to mindfulness, encouraging people to connect with both the aquatic environment and themselves. “We just want to get people onto the water,” says Lennert, “and to help them see a different side of the city.”

Best GTA Put-ins
Beyond Cherry Beach, the Spit and Islands, Lennert has a handful of other favourite put-in spots. To surf, Woodbine Beach and the Scarborough Bluffs are your best bet, especially when the wind is whipping in fall and winter. The Humber River and the Rouge River carve through fairytale valleys, perfect for exploring on a SUP. East of the city, the wildlife-rich Rouge is part of the protected Ontario Greenbelt, where the second most popular recreational activity is paddling (drawing over 2 million people and generating hundreds of millions in economic value every year). Public transit makes it easy to zip around and do one-way trips with inflatables like Red Paddle Co’s new 9’6” compact board.
Olympic Paddler Larry Cain on SUP
On the opposite side of the Greater Toronto Area, in Oakville, Larry Cain also makes his living through SUP. An Olympic gold and silver medallist sprint-canoeist turned paddleboard racer and instructor, he runs an online coaching site—paddlemonster.com—and has travelled to Hawaii to train world-champion waterman Connor Baxter. Almost as impressive, the 56-year-old is on LakeOntario about 340 days a year.
“Once you learn how to become stable, it’s like strolling on the sidewalk…”
Cain got into dragon boat and outrigger canoe racing after his national-team career and reluctantly stepped onto a SUP at a race around 2010 when a friend insisted he give it a try. He was struck by the similarity to canoeing (in the stroke), and how subtle muscle shifts had an immediate impact on how the board was moving. Captivated by this intimate connection to the water, and an opportunity to discover something new, Cain dons a drysuit and hops onto his narrow 14-foot hard shell on frigid February mornings. It’s not as cold as walking the dog, and nowhere near as dangerous as driving. “Once you learn how to become stable,” he says, “it’s like strolling on the sidewalk. Then you learn to play with the waves and wind, to make the most of what the lake is offering. It’s an amazing way to get out into nature without a yacht or sailboat. SUP is so simple. It’s the optimal human-powered watercraft. You can do it entirely on your own terms.”
After a laid-back traverse of the islands’ canals, passing cottagey houses and stopping for a dockside picnic, my friend and I carry our boards across a grassy field to a breakwater that borders the vast expanse of Lake Ontario. We jump in for a short restorative swim and dry off quickly with the southwesterly breeze and hot sun at our backs on the paddle home.—ML