Given that you live in Toronto, I'd suggest that you consider joining Harbourfront Centre Sailing and Powerboating (HCSP) Club on Queen's Quay. The marina and club house are located at the intersection of Queen's Quay and Reese Street.
The club has a fleet of shared sailboats ranging from 20 to 35 ft which are available to members at no marginal cost. You can either skipper yourself or go out with someone more experienced as crew. There are a number of race nights and social sails every week.
It is by far the most cost-effective way to actively sail in Toronto.
HCSP is having an open house weekend on April 27 and 28th (look it up). You can check out the boats and get free rides
I've been a member for the past couple of years and have greatly enjoyed it
Hope this helps,