Sorry it took me a few days to find this thread. Ann and Stu are right, I'm in Vancouver with trentepieds and this is a very convenient place for you to learn keelboat sailing once you've done an intro course on smaller boats on the Glenmore reservoir in Calgary.
You didn't mention your time frame. I would recommend, if you can, taking an intro course cheaply in Calgary and then coming out and doing a weeklong live-aboard course in Vancouver. You could then find an arrangement (co-op, club, partnership
, charter) to spend some time sailing these waters in a 27' boat for about $5-7k.
I would actually recommend doing the course in Vancouver since there are a lot of great clubs and schools here, but putting the boat in Sidney. The cruising is way better there, especially in a smaller boat as you are right in the heart of the Gulf Islands, moorage is cheaper, and there are plenty of direct flights to Calgary (YYJ is actually in Sidney, not Victoria).
Here are a couple articles on ways to learn to sail
and buying your first boat
. Drop me a line if there's anything else I can help with.