This article is from the Boats FAQ, by John F. Hughes with numerous contributions by others.
The Sunfish and boats like it_very simple, easy to rig and to move
around_make great learning boats for one or two people, but not for a
family. The Laser is a tougher first boat, but there's likely to be a
racing fleet nearby, and you can get an old one that's still plenty
strong for very little money.
My own belief is that a somewhat tired old boat is a good first
one. It will teach you something about maintenance, and it will let
you take some risks as you're learning_scratching an already-scratched
hull is far more tolerable than scratching a brand-new one.
In general, a boat that can be trailered and handled by one person is
probably best; you'll sail lots more if you don't have to get a friend
to help out.
Sailing clubs can be a great way to learn. (jh)