The best way to learn to sail is different for each sailor; everyone has different talents, experience, limitations,
budget, risk tolerance, interests, and dreams... and these can change. Depending upon the above, you might get something out of
-- sailing clubs, co-ops, and community sailing centers,
--
books, videos, web sites and blogs,
-- generic basic
boating education
classes by state organizations, US
Power Squadrons, Coast Guard auxiliary, etc. (or joining them and getting more training),
-- signing up on crew lists at local yacht and sailing clubs and national web sites and
forums,
-- meeting sailors wherever they gather,
-- seminars and talks sponsored by
marine chandleries and organizations,
--
learning the "fine art of dockwalking" and bumming rides,
-- sharing the cost of a
charter or instructional
charter,
-- hiring an instructor/skipper outside of a
sailing school program,
-- swapping off
skipper and crew roles with other sailors on your boat and their boats,
-- volunteering to help with
race committee and watch lots of boats in action at sometimes close range -- sometimes a very good way to observe what they are doing right and wrong,
--
buying a small sailing
dinghy with which to
experiment and learn basic skills.
Expense of learning is rather relative, since a good instructor and class might save
money down the road... boat
ownership as you already know is very flexible about how much of your
money it can soak up and anything that saves you from making a dumb mistake or bad habits could be worth something.