The outrigger canoe was one of the key technological innovations of the Austronesian peoples. Although there is little archeological evidence due to perishable building materials, comparative reconstructions indicate that Austronesians already had the distinctive outrigger and crab claw sail technology from at least 2000 BCE. These boats (as well as derivative technologies like the catamaran) enabled them to colonize the islands of Southeast Asia and then later on to Madagascar, the Pacific Islands, and New Zealand.
Outrigger canoes like the va'a, paraw, jukung, vinta, and proa are still used today by traditional fishermen and traders in most of Southeast Asia and Madagascar, and in parts of Oceania. They are constructed from traditional materials, though most incorporate motor engines instead of a sail.
In other regions like Hawaii, Tahiti, and New Zealand, outrigger canoes are generally restricted to sport sailing and racing. Modern sailing outrigger canoes are usually made from glass-reinforced and carbon fiber-reinforced polymer, with sails made from Dacron and Kevlar.
The Hōkūleʻa is a modern interpretation of a Polynesian voyaging canoe. It is made from modern materials such as fibreglass, plywood, resin glue, terylene sails and ropes with modern fittings and safety equipment. No authentic Polynesian voyaging canoe has ever been seen although numerous catamaran types were seen by Europeans from the 18th century. Voyaging canoes have crossed the Pacific many times. In most voyages they have been escorted, or towed, by a modern mother ship.
John MacGregor of Scotland is generally believed to have developed the first modern sailing canoes. During the 1860s, he had at least seven boats built that he called Rob Roys and sailed and paddled them in Europe, the Baltic and the Middle East. He also wrote a book which popularized the design and the concept: "in walking you are bounded by every sea and river, and in a common sailing-boat you are bounded by every shallow and shore; whereas, ...a canoe [can] be paddled or sailed, or hauled, or carried over land or water" (1000 Miles in the Rob Roy Canoe).
MacGregor founded the British Royal Canoe Club (RCC) in 1866.
The New York Canoe Club followed about six years later.
The American Canoe Association (ACA) was founded in 1880. In 1883, ACA Secretary Charles Neide and retired sea captain “Barnacle” Kendall paddled and sailed over three thousand miles from Lake George, New York to Pensacola, Florida.
In 1886 the ACA and the RCC held the first international canoe sailing regatta.
In 1991 American Howard Rice sailed and paddled a sailing canoe solo around Cape Horn, Chile considered historically to be the Mount Everest of sailing challenges. He was awarded a Certificate of Merit by the Chilean Navy and inducted into the Cape Horners Society.