Cherry Beach is the perfect place to catch the breeze and rip across the Toronto Waterfront. The channel between Cherry Beach and Tommy Thompson Park provides few waves but awesome wind at the city's doorstep.
Head down to the Toronto Windsurfing Club at Cherry Beach to join sailors any day of the week for a cruise along the waterfront. Membership to the club will grant you parking and clubhouse access, plus equipment storage. For the day-trippers, this is a great spot to surf alongside many experienced sailors with the city skyline as your backdrop.
Head down Regatta Road to the very end and find the Toronto Windsurfing Club on the right. You can also cast off from the public beach at the end of Cherry St. Lessons are available from the club as well, highly recommended if you are a beginner as the wind can make it challenging to get back to shore.