Sailing employs the wind—acting on sails, wingsails or kites—to propel a craft on the surface of the water (sailing ship, sailboat, raft, 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.

From prehistory until the second half of the 19th century, sailing craft were the primary means of maritime trade and transportation; exploration across the seas and oceans was reliant on sail for anything other than the shortest distances. Naval power in this period used sail to varying degrees depending on the current technology, culminating in the gun-armed sailing warships of the Age of Sail. Sail was slowly replaced by steam as the method of propulsion for ships over the latter part of the 19th century – seeing a gradual improvement in the technology of steam through a number of stepwise developments. Steam allowed scheduled services that ran at higher average speeds than sailing vessels. Large improvements in fuel economy allowed steam to progressively outcompete sail in, ultimately, all commercial situations, giving ship-owning investors a better return on capital.^: 9, 16

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 which are 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.