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Teaching Yourself to Sail
When contemplating how to make the transition from a landlubber to someone who can leave and return to the dock under sail in a seaman like fashion, it may be helpful to remember that all sailors started on land. Despite the grace with which you may watch some sailors maneuver their vessels, no one is born with the set of skills that comprise good boat handling and there is no substitute for hard-won experience. The question is how to get out on the water and glean the insight that will make you a better sailor.
Although plenty of sailors have started with little idea of what they were doing and subscribed to the I'll-figure-it-out myself philosophy, buying, renting, borrowing, or otherwise obtaining a boat for your first sail without appropriate seafaring skills can be hazardous to your health. Blindly throwing your fate to the wind and wave gods is a potentially dangerous thing for several reasons. Most neophytes have been insulated from Nature by office walls and automobiles and are unaccustomed to observing wind direction, currents, and tides in their everyday lives. Sailing engages all of these elemental forces.
Even if the wind is blowing hard enough to permit monitoring its direction, there is the question of how to harness the force with an unfamiliar assembly of ropes and pulleys. A flying boom from an unintentional and unexpected jibe can do serious damage to a tender skull, to say nothing of the hypothermia that can result if you end up in the water. Add waves pounding on nearby rocks, traffic from other boats and ships, and the first time out could scare you enough to be your last. If you insist on making a solo run of it, use common sense and be prudent. Reading beforehand will take some of the mystery out of what is happening. Understanding the theory behind how the boat is moving will make learning on the water easier and safer. Wear a life jacket. Don't go out on an overly windy day. A small body of water with light traffic is a better choice than a large body of water with plenty of boats. Be cautious and at least recognize the fact that you don't entirely know what you are doing. Know that it is easier to go down wind than it is to go up wind. Finally, have someone standing by in case you'll need rescuing.