Join Date: Feb 2000
Location: Annapolis, Md
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I would say that there isn't just one good way to start, but many. For some, the answer is get and read through a good book on sailing (I usually recommend "Basic Keelboat" which is US Sailings manual, and "Sailing for Dummies" by by JJ and Peter Isler which is actually the more thorough of the two), sail a couple times with friends and don't be afraid to ask questions. And then either rent or buy a small boat and sail the living daylights out of it.
If you are reasonably agile, and can sail on reasonably protected waters with reasonably reliable winds, then I would suggest that you look for a small dinghy, ideally one that is popular in your area and perhaps a bit more modern than a sailfish so that you won't out grow it too soon.
If you are not all that agile, or you are not sailing on a protected body of water with reliable winds, then I suggest that you try to buy a used, 22 to 28 foot, fin keel, spade rudder, moderately light weight sloop which should be responsive enough for you to develop boat handling and sail trimming skills.
You may only own this boat for a short time so try to buy one that is in reasonably good shape, but not perfect, and that is common in your area.
As you start spending time on the water, you will start to develop some skills and a whole lot of questions. Continue reading and asking questions.
Now then, there are people who who have trouble learning something that is as complex as sailing. Having taught a lot of people to sail in my life, there is something about having a few lessons to help walk you through the basics. Having spoken to a number of people who have taken both the ASA and the US Sailing courses, it would appear that the US Sailing courses are a bit more detailed. For some that meant information overload and for others it meant a better value for the dollar.
However, you get your 'fundamentals' there is nothing like simply getting out there and doing to build skills.
If you are not in a position to actually own a boat, then I suggest that perhaps try to get aboard a race boat. Racing crews rarely have a lot of time to teach you what to do during a manuever, but you can probably a position as a grinder and rail meat, which will give you a chance to watch things first hand and ask questions between tacks and jibes. Just eb aware that when people are quiet they may be concentrating on wind patterns or the competition, and ask "Is this an okay time to ask a question? before blurting out what is on your mind.