I used to sail my Bravo and Adventure Island in Lake Ontario. There are a lot of days where it's not so bad out there, even for learning, just dress for the cold water.
I'm going to be doing some sailing at Belwood Lake and Guelph Lake, both of which have small boat sailing clubs.
Here's a link to Belwood Lake. The launch area is just to the west of where 4th line ends. If you zoom in, you can see it. The sailing club is tougher to see on Google Maps, but they launch just north of where the public launch is.
It looks small on the map, but here's a video taken of their sailing club last year (I found it online) this is in the south narrow part of the lake, and you can see there's plenty of room to get around, and the sailing club seems to have at least one active Hobie Catamaran, and I've seen a few more out there.
Following is the Link to Guelph Lake. I haven't been there yet, so I'm not exactly sure of their launch area or anything else.
Bring a little bit of cash. There's a small entrance fee for the conservation area, where the launch area is located. I can't remember the cost, something like 4 or 5 bucks. You can also get a yearly pass which allows you in to all of the Grand River Conservation areas.
$5 isn't bad, thats less than parking in most places.
Out of curiosity have you tried Kelso lake? It's not large by any means but its only 15 mins away, and it might be good to learn to sail someplace I can swim across but then again it could be so small as to be a waste of time.
Also, I found a Hobie Cat club at the burlington lakeshore. I havn't had a chance to swing by yet but have you any experience with them?
Yeah, don't quote me on the cost, but it's not prohibitive.
I haven't tried Kelso, it looks big enough, but it's on the edge of the ski hill, and I wonder if that would rob it of some wind compared to lakes that don't have a lot of elevation right next to them. I could be wrong about that though.
I used to live in Toronto until this winter, so I never had a reason to go to Burlington to sail the same lake. I haven't hooked up with Hobie Cat groups anywhere, mostly because they're usually more 16's and my Bravo isn't really in that sailing class. I'd like to meet up with them for social reasons, and I'd love to learn to crew a bigger boat, but life kind of gets in the way of that sometimes. If you have a 14, it's worth seeing who's there, if they're anything like the sailors on this board, they'll be a very helpful group!
From what I've heard, Belwood seems to be the gold standard for sailing smaller lakes in this area, but I've looked at Mountsberg Reservoir and even went sailing on Fairy Lake in Acton a few days ago. It's TINY!! Just barely big enough for my Bravo, but I'm sure it'll be too small for a faster boat like the 14.