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 developmental steps. 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.

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.

Throughout history, sailing was a key form of propulsion that allowed for greater mobility than travel over land. This greater mobility increased capacity for exploration, trade, transport, warfare, and fishing, especially when compared to overland options.

Until the significant improvements in land transportation that occurred during the 19th century, if water transport was an option, it was faster, cheaper and safer than making the same journey by land. This applied equally to sea crossings, coastal voyages and use of rivers and lakes. Examples of the consequences of this include the large grain trade in the Mediterranean during the classical period. Cities such as Rome were totally reliant on the delivery by sailing ships of the large amounts of grain needed. It has been estimated that it cost less for a sailing ship of the Roman Empire to carry grain the length of the Mediterranean than to move the same amount 15 miles by road. Rome consumed about 150,000 tons of Egyptian grain each year over the first three centuries AD.

A similar but more recent trade, in coal, was from the mines situated close to the River Tyne to London – which was already being carried out in the 14th century and grew as the city increased in size. In 1795, 4,395 cargoes of coal were delivered to London. This would have needed a fleet of about 500 sailing colliers (making 8 or 9 trips a year). This quantity had doubled by 1839. (The first steam-powered collier was not launched until 1852 and sailing colliers continued working into the 20th century.)

The earliest image suggesting the use of sail on a boat may be on a piece of pottery from Mesopotamia, dated to the 6th millennium BCE. The image is thought to show a bipod mast mounted on the hull of a reed boat – no sail is depicted. The earliest representation of a sail, from Egypt, is dated to circa 3100 BCE. The Nile is considered a suitable place for early use of sail for propulsion. This is because the river's current flows from south to north, whilst the prevailing wind direction is north to south. Therefore, a boat of that time could use the current to go north – an unobstructed trip of 750 miles – and sail to make the return trip. Evidence of early sailors has also been found in other locations, such as Kuwait, Turkey, Syria, Minoa, Bahrain, and India, among others.