Generally speaking, you will learn faster and become a better sailor if you learn first on small boats. An error on a small boat is magnified, whereas larger boats can be more forgiving of mistakes, you want to know what went wrong so that you can avoid it in the future. Likewise, larger boats are usually more expensive. Most sailing schools start you off with small boats and work you up to larger ones. There may be local clubs, volunteer organizations, or informal groups that can impart the skills you need. The US Coast Guard Auxiliary and the US Power Squadron teach courses covering topics ranging from basic navigation to diesel engine maintenance. Finally there are national schools and certification levels—US SAILING and American Sailing Association are among the most widely recognized. Their programs teach several levels of certification from small dinghies to basic keelboat handling, and successful completion of the courses yields certification recognized by many charter companies. Coastal cruising and overnight passage-making are taught, and there may be additional classes in celestial navigation and piloting. Prices can range from a few dollars at a local club to six three-and-a-half-hour lessons for $700, or three eight-hour days at $450, so again, do some research since prices can fluctuate based on season and demand. Best of luck to you.
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Sailing
schools can help you accelerate up the learning curve and
they provide a comprehensive skill set, allowing you to take
a boat out safely and with confidence.