This is not a casual paddle. The route from Cherry Beach to Centre Island demands respect, strong technical skills, and sound judgment. But for experienced paddlers ready for the challenge, it offers something Toronto‘s quieter routes cannot.
The opportunity to navigate a genuine urban water crossing, witness the city’s maritime infrastructure up close, and emerge into a wild, sheltered world that feels impossibly removed from downtown traffic. You’ll test your paddling ability against Lake Ontario‘s conditions, share the water with commercial shipping, and discover why this route captivates advanced paddlers year after year.
The challenge begins almost immediately. From Cherry Beach, you must cross the Eastern Channel, Toronto Harbour’s main commercial shipping route. Around 300 meters of open water separate you from the islands, with ferries, sailboats, speedboats, and even massive freighters constantly moving through the harbour. Kayaks are easy to miss, so the crossing demands focus, awareness, and confidence. Many paddlers say it is the most exciting part of the route because, surrounded by large vessels and open water, you suddenly feel minimal.
Where The City Suddenly Disappears
Once you make it across, the atmosphere changes completely. The busy harbour gives way to calm lagoons, narrow creeks, and quiet marshlands that wind through Centre Island. City noise fades into the background as herons fish along the shoreline and geese nest in the reeds. It feels like genuine wilderness sitting just minutes from downtown Toronto.
The route can vary significantly depending on how many of the islands you explore. A direct paddle is about 6.6 miles, but most kayakers spend hours weaving through hidden channels, quiet lagoons, and narrow creeks connecting the islands.
That is when the experience becomes almost meditative, the complete opposite of the intense harbour crossing. You glide silently through calm waterways, pass beneath low branches, and see a side of Toronto that most people never experience.
This route is best suited for experienced paddlers who are comfortable with open-water crossings and changing harbour conditions. A PFD is essential, and checking wind, weather, and vessel traffic before launching is part of the experience.
Together, the challenge and calm create one of the city’s most unforgettable paddling experiences.
The Need To Know Details
Best season: May through October. Fall is ideal for calm conditions and fewer crowds. June onward if paddling without thermal protection
- Distance: 6.6 miles minimum. Varies significantly based on interior channel exploration. Half-day to full-day paddle
- Difficulty level: Advanced. Requires experience with open water, strong paddling skills, and traffic awareness
- Launch point: Cherry Beach, 1 Cherry Street, Toronto. Free parking, but it fills quickly on weekends
- Safety requirements: Personal flotation device (mandatory), thermal protection (wetsuit/drysuit essential early/late season), full awareness of vessel traffic
- Equipment rental: Toronto SUP: 647-546-4787, torontosup.com. Paddle Pirates: 416-203-2277, paddletoronto.com
How To Get There
- By transit, take the streetcar to Cherry and Commissioners, a short walk to the beach. Once at Cherry Beach, you’ll see the launch area on the sandy shore. This is where experienced paddlers prepare for the crossing.
- If driving, free parking is available in the lot next to the beach, though it fills quickly on warm weekends—arrive early.
