Best way to learn how to sail?
Having taught probably hundreds of people to sail over the years, it is posible to teach yourself to sail by reading and spending a lot of time on the water, but it is much easier to either have an introductory course or to have someone coaching you a little during the process. Depending on where you are based there are often low cost courses covering many of the aspects of boat operation offered through Community Colleges, the Red Cross, Power Squadron, and Coast Guard Auxillary.
There are a whole range of sailing schools out there. Steve Colgate''s schools always gets high marks. J-world offers a more performance oriented program. Boat shows will sometimes have intro to sailing seminars.
You can also often get to sail with other, more knowledgeable sailors. Local sailing magazines and websites often have the names of people looking for crew. Local sailing clubs will often have members who are looking for crew. Here on the Chesapeake, local municipalities sometimes run one day intro to sailing days.
Then there is the issue of how well you wish to sail. As Ihave said quite a few times on this BB, we each decide how good a sailor we would like to be. Some of us prefer to really understand how to sail well. Others only want to know enough to get the boat out of a slip and sail her home safely.
If you really want to learn to sail well, I would suggest that your first boat either be a small daysailor or dinghy (13-16 feet) if you are athletic or else a 23 to 28 foot, responsive fin keel-spade rudder sloop. These types of boats will give the kind of feedback that will greatly accellerate your learning process.
In the end,learning to sail comes down to how well you want to learn, reading, getting lots of time on the water, and that other intangible quality, whether you have an aptitude for sailing.