Sailing employs the wind—acting on sails, wingsails or kites—to propel a craft on the surface of the water (sailing ship, sailboat, windsurfer, or kitesurfer), on ice (iceboat) or on land (land yacht) over a chosen course, which is often part of a larger plan of navigation.

Sailing craft and their rigs
Three-masted barque with square sails
Class 3 competition land yacht

Until the middle of the 19th century, sailing ships were the primary means for marine exploration, commerce, and projection of military power; this period is known as the Age of Sail. In the 21st century, most sailing represents a form of recreation or sport. Recreational sailing or yachting can be divided into racing and cruising. Cruising can include extended offshore and ocean-crossing trips, coastal sailing within sight of land, and daysailing.

Sailing relies on the physics of sails as they derive power from the wind, generating both lift and drag. On a given course, the sails are set to an angle that optimizes the development of wind power, as determined by the apparent wind, which is the wind as sensed from a moving vessel. The forces transmitted via the sails are resisted by forces from the hull, keel, and rudder of a sailing craft, by forces from skate runners of an iceboat, or by forces from wheels of a land sailing craft to allow steering the course. This combination of forces means that it is possible to sail an upwind course as well as downwind. The course with respect to the true wind direction (as would be indicated by a stationary flag) is called a point of sail. Conventional sailing craft cannot derive wind power on a course with a point of sail that is too close into the wind.