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Sailing is something you have to learn in steps. If you don't master the basics such as winch safety, anchoring and trimming a sail, you'll never understand how to manage difficult sailing situations such as heavy wind, a rudder breaking or bad weather. If you don't know how to manage the helm, you'll never feel comfortable going farther away from shore. That's why the US Sailing Association has determined seven levels of standardized training which must be taught by certified instructors. When you begin at the first level, Basic Keelboat, you'll begin a log book in which you'll record all your course completions and the stickers sent to you by US Sailing. This information will also be submitted to a national database and your official log book will serve as a passport for renting or chartering boats locally and around the world (once you receive the proper certifications).
After Basic Keelboat you will progress to Basic Cruising certification, allowing you to advance to larger boats with hull sizes as big as 35 feet. You'll spend more time docking and learning the handling maneuvers of larger boats. Once you earn this certification, you'll be ready to take your family on a day trip.
After you get enough experience day-sailing larger keelboats, you can move to Bareboat Cruising, Passage Making and Coastal Navigation certifications. By this time you'll be an experienced sailor capable of dealing with difficult situations like current and wind. You'll also be skilled at dead reckoning techniques, chart reading and deteriming fixes (your position).
If you choose a sailing school, make sure your instructors have been certified by US Sailing. If they have, they will then be able to offer US Sailing certifications upon successful completion of courses and you can feel safe that the curriculum was adequate. For more information, visit ussailing.org.