Joeb1, Good for you for reaching out.
Hopefully others will start chiming in with advice but till then here is a little from a fellow Torontonian who has finally managed to realize the dream (if not totally).
For the past few years I have taken family
friends around your age with us when cruising and have always held open spots for those that wanted to see what the Islands and cruising were all about, I only regret not having more space and more time as there is a lot of you out there. I don't think I alone in doing this and my suggestion to you would be to get to know as many sailors at as many of the clubs within your reach that you can, you will be surprised at how many of us have boats in the various Islands over the winter and would welcome an eager helping hand on some of the trips we have to make to move the boats around. The fact that you pay your way is a big bonus. Please also be very aware of the people and the boat
you do get to go on, your safety
is as much your own responsibility as it is the captain
of the boat.