Re: Overwhelmed sailing novice seeks advice
You could try the Humber College Sailing Club on your own doorstep.
Humber Sailing Club
If you want some Caribbean sailing experience you can charter and get a skipper / instructor.
ISPA Yachtmaster Offshore Instructor Evaluator
Sail Canada Advanced Cruising Instructor
IYT Yachtmaster Coastal Instructor
As I sail, I praise God, and care not. (Luke Foxe)