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This is my favorite afternoon, evening, or day trip in Toronto is a trip around Toronto Islands, just a kilometer offshore (at the widest point). The trip around the islands can be varied from a quick crossing to weaving between islands and or circumnavigation. This is one of the reasons I like this trip. Very easy to get to, and the return on time invested is extremely high.
On the far side of the islands are a few of beaches (just a note - July & August one of them is a clothing optional beach). There are also picnic sites available along the far side of the island with charcoal grills for those wanted a real picnic trip with spectacular views of Lake Ontario and nice beaches.
My favorite part of the trip though is crossing the Toronto harbor itself. While there can be some boat traffic, most of it is limited to tourist boats. The views of the city are just as beautiful as one could imagine. Another point of interest in crossing the harbor is that you cross the flight path for small planes landing and departing the downtown city airport. This day in particular I saw a number of biplanes and other interest craft. There are buoys clearing marking the outer limits of the approach zone for the active runway and are to be avoided.
The weather can get very choppy even in the harbor depending on wind so the crossing itself can be moderately challenging to a novice. Circumnavigating the islands themselves can fall into the experts only depending on the wind direction. If the winds are from the south, the fetch is about 50km. I've paddled 3-meter waves. If the wind is from the SE the fetch is about 249 km. I've paddled 4-meter waves. Again this is on the far side of the island out in the open lake. I'd recommend circumnavigation when the winds are from due north. It's as calm as can be both in the harbor and on the far side of the islands.
The best place to launch is directly next door to a marine police station on Queens Quay along the lakefront downtown. You can drive within 50 meters of the launch platform (yes, I love launch platforms, tilted and carpeted) that is located at Harborfront Canoe and Kayak Centre, a local place where you can store or launch your kayak, or learn to become an expert from their staff. They don't charge a fee for launching and parking is less than a block away.
Heel and Pegpads™
Hardshell Kayak Sail Rigs