Sailing and yachting as a New Zealand sport dates from 1841 when a regatta was held on Wellington Harbour (Port Nicholson) to celebrate the first anniversary of the settlement. The report in the New Zealand Gazette and Wellington Spectator was as follows:

The Wellington Anniversary Regatta was a regular annual fixture organised by a committee of prominent citizens under the patronage of the Governor, but in 1883 the newly founded Port Nicholson Yacht Club took over its management. Auckland, now the largest yachting centre of the colony, did not hold its first regatta until 1850. These events were repeated at irregular intervals until 1880 when the now famous Auckland Anniversary Regatta became an annual fixture. It has been reliably estimated that no other yachting regatta in the world draws a larger fleet. Today, Auckland accounts for over 80 per cent of New Zealand's total yachting population.

A factor which afforded considerable stimulus to the growth of the sport in the Auckland area was the large number of small sailing vessels which were engaged in the local and Pacific Islands trade. Trading vessels participated in the anniversary regatta until the turn of the century and, even after the arrival of steam, their influence was carried on. The popular Mullet Boat class is a direct descendant of one type of commercial vessel well known on the Hauraki Gulf in the past.

Two notable Auckland boatbuilding families, those of Robert Logan and Charles Bailey, were responsible for much of the development in design and construction methods which took place in the late nineteenth century. To them is the credit largely due for the fact that, at the turn of the century, New Zealand yacht design was on a par with that of contemporary British and Naval architects and boatbuilders, while New Zealand construction was superior. Logan pioneered the three-skin diagonal method of construction which is now generally recognised throughout the world. Many of the yachts built by Logan between 60 and 70 years ago using this method are still in active use throughout the country. The Rona, built for A. H. Turnbull to the design of the famous British architect, G. L. Watson, in 1893, is still winning races in Wellington. Eight of the yachts racing in the Auckland first-division fleet today are over 60 years old, Rainbow, Ariki, and Iorangi being the most notable.

The great majority of yachts sailing in New Zealand waters are of the small centreboard classes of which there are over 37. Most of these sail both in club and in provincial competition, and for some classes there are annual national championships sailed on an interport or provincial representation basis. The most notable national championship up until recent years has been the Sanders Cup series for 14-ft X-class boats. The championship was named after Lieutenant W. E. Sanders, V.C., D.S.O., a New Zealand naval hero of the First World War. These boats were originally known as the Rona-Jellicoe class after the then Governor, Earl Jellicoe, who was a prominent founder member of the class during his term of office (1920–24). Lord Jellicoe was a contestant in several national contests and represented Auckland in the first Sanders Cup series in 1921 which was won by Heather, of Otago.