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Offshore Sailing School Tip: If you want to win a sailboat race, the key is to make a very detailed plan...and then be ready to scrap it. Before sailboat racing, you'll need to know the ins and outs of the boat, the crew, the water, the weather (as much as you can predict it for the race day), the course, and how to make the boat work to its maximum potential. And practice, practice, practice! Once you begin the race, however, anything can happen. Weather can change, a competing boat and crew could be better (or worse) than you anticipated, etc. In sailboat racing, be willing to throw out all pre-planning in an instant and work with the immediate situation at hand. This is where your in-depth knowledge of boat and crew will be most useful.