Dinghy sailing is the activity of sailing small boats - usually for recreational purposes, learning necessary sailing skills (often also within family), and competition.

RYA lists Five essentials of sailing dinghies as:

When racing, the above skills need to be further developed and additional skills and techniques learned, such as the application of the "racing rules of sailing", boat handling skills when starting and when rounding marks, and knowledge of tactics and strategy. Racing tactics include positioning the boat at different angles. To improve speed when racing, sailors should position themselves at the windward direction (closest to the direction of the wind) in order to get "clean air".

The RYA, the regulating authority for sail training in the UK, states that, "With a reliance on nature and the elements, sailing ... is about adventure, exploration, teamwork and fun."

There has always been a need for small tender boats for transporting goods and personnel to and from anchored sailing ships. Together with other smaller work craft such as fishing and light cargo, small inshore craft have always been in evidence. Charles II of England had a private sailing boat presented to him when he returned from exile to England in the 17th century, and he sailed for recreation and competition.

In 1887 Thomas Middleton, a Dublin solicitor, considered that yacht racing was becoming an excessively expensive activity, with boats becoming eclipsed by better designs each year. He proposed the 'One Model' principle. He wanted yacht racing to be an exercise of skill with all boats being built to the same design. He assembled a group of potential owners who agreed to call the boat 'The Water Wag'. The Water Wag Club still prospers in Dún Laoghaire harbour, with racing each Wednesday evening during the summer season.

Towards the end of the 19th century people began to use these small boats for sport and recreational sailing, utilising the opportunities for leisure afforded by the Industrial Revolution. Larger privately used sailing boats had developed separately, and have resulted in the yachts of today. There has been some crossover, in that the sloop sail plan was adopted as standard and most convenient by early dinghy designers.

The development of the sailing dinghy was helped in the early 20th century by Uffa Fox (1898–1972), an English boat designer and sailing enthusiast. He developed and contributed to many dinghy classes that are still with us nearly a century later: the Albacore, International 14, National 12, Jet 14, Firefly and Flying Fifteen. The Scorpion was designed in 1959 by Taprell Dorling.