Sailing is the guidance of a ship across a body of water by using large surfaces called sails that provide propulsion when placed in the wind. Prior to the invention of more efficient means of propulsion, sailing was the primary method of traversing Earth's oceans. After the invention of other means of propelling a ship, sailing became mainly a recreational activity.

Captain James T. Kirk maintained a sailing ship that he used during shore leaves on Earth. (TOS novels: Dreadnought! and Battlestations!)

As a Lieutenant, Geordi La Forge once built a replica of an old Royal Navy sailing ship, the HMS Victory.

Lieutenant Commanders Geordi La Forge and Data once went sailing on a lake during short leave when Data decided to go for a swim. However Data was unable to maintain buoyancy, and sank to the bottom. Data was forced to walk along the bottom of the lake for over a kilometer to shore. (TNG episode: "Descent")

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