Whilst sailing's invention is prehistoric, racing sailing boats is believed to have started in The Netherlands some time in the 17th century, whence it soon made its way to England where custom-built racing "yachts" began to emerge. In 1851, a challenge to an American yacht racing club in New York led to the beginning of the America's Cup, a regatta won by the New York Yacht Club until 1983, when they finally lost to Australia II. Meanwhile, yacht racing continued to evolve, with the development of recognised classes of racing yachts, from small dinghies up to huge maxi yachts.
These days, yacht racing is a common participant sport around the developed world, particularly where favourable wind conditions and access to reasonably-sized bodies of water are available - most yachting is conducted in salt water, but smaller craft can be and are raced on lakes and even larger rivers.
Whilst there are many different types of racing vessels, they can generally be separated into the larger yachts, which are larger and contain facilities for extended voyages, and smaller harbour racing craft such as dinghies and skiffs.
Dinghy races are conducted on sheltered water on smaller craft, usually designed for crews of between one and three people. They are almost all equipped with one mast. Some have only one triangular sail, but most have two configured as a sloop, and usually carry a spinnaker, a large, bulging sail designed for sailing "with the wind". Most races are conducted between vessels of identical design ("one design" racing). In these races, with identical equipment the sailors best able to make use of the ambient conditions win.
Dinghy designs vary from small, stable, and slow craft for novice sailors to lightweight, high-speed designs that are very difficult for even experienced crews to sail safely and effectively. Australia's 18-foot skiff class are the fastest monohull dinghies, reaching speeds of up to 40 kilometres per hour even in relatively light winds. Sailing has a reputation for being a boring spectator sport, but skiff racing can be very exciting, particularly in unpredictable conditions where crews struggle to keep their boats upright. Various multi-hull racing classes are even faster.
Various one-design dinghy classes are raced at the Summer Olympic Games. Larger yachts are also raced on harbours, but the most prestigious yacht races are point-to-point long distance races on the open ocean. Bad weather makes such races a considerable test of equipment and willpower just to finish, and from time to time boats and sailors are lost sea. The longest such events are "round-the-world" races which can take months to complete, but better-known are events such as the "Fastnet race" the United Kingdom and the Sydney to Hobart yacht race along the east coast of Australia. As well as a first-past-the-post trophy (called "line honours"), boats race under a handicap system that adjusts finishing times for the relative speeds of the boats' design, theoretically offering each entrant an equal chance.
Cruising is traveling on a boat. It could be a trip to the other side of the bay or across the ocean to the islands of the South Pacific. Safe cruising across long distances requires a degree of self sufficiency and a wide range of skills beyond handling the boat. Knowledge of map reading and navigation, meteorology, mechanics, electrical systems, and more can be helpful or even life saving when cruising to distant ports.
See also: Dennis Conner, Dinghy sailing.