Records of the island's oldest sailing club go back as far as 1896, as evidenced by this well established sailing programme. Unfortunately, the exact date the club was founded is currently unknown and assumed to be the late 1800s.

Originally called the Sheerness Sailing Club, the name was changed in 1935 to Sheppey Yacht Club, before becoming the Isle Of Sheppey Sailing Club in 2002.

The object of the club has always been to encourage and promote the wonderful sport of sailing and to provide sailing facilities for local people and the wider community.

Originally, the club was based at Queenborough, and to this day still has a small boat compound there. In the early days there were dinghy, yacht and cruising members. 

In 1978, the 'yacht' owners decided to form themselves into the Queenborough Yacht Club, leaving IOSSC as a dinghy sailing club.

The famous IOS Round the Island Race was first held in 1959 and was orignated by Mr. Keith Broughton, the sailing secretary at the time. The race started on the west side of the Kingsferry Bridge and finished at Ridham Dock. The inaugural race was won by P. G. Harris, the treasurer of Gravesend Sailing Club, sailing a Snipe.

In the early 60's the race started at Queenborough and finished at Ridham Dock or just after the bridge, before moving to the modern course - a full circumnavigation of the island starting and finishing from Sheerness.

At the start of the 60's Sheerness Council were preparing a development plan to improve the sea front. Broughton was employed as a draughtsman at the council and in the course of his work was required to help prepare the plan.

Broughton produced a scheme and included drawings for a proposed Yacht Club at Cheyne Rock - ideal due to the best tidal properties of any site on the north coast of Sheppey, able to support launching and recovery of small boats at any state of tide.

Because of the excellent tidal properties at this point, the site had previously been used as a coal depot for over 100 years by the Sheerness Cooperative Society. Coal was bought in by barge to a short pier (the remains of which can still be seen today in the form of wooden stumps embedded into the promenade).

Broughton persuaded his superiors that this feature would be an asset to the Council and Community and also suggested that Sheppey Yacht Club might be interested in the tenancy. As a direct result the officers of the club were invited to a meeting with Council.

Shortly afterwards Broughton accepted a post with another council. A colleague promised to do his best to see that his scheme was carried through. Work started on the new building at the end of 1963 but the original contractors made such slow progress that the council had to terminate their contract and start again.

The purpose-built club house was finally finished at the end of 1965. The Duke of Edinburgh, Prince Philip, a keen sailor, was due to officially open the new building but had to decline due to an "unusually heavy" summer programme.

The clubhouse was officially opened in 1966 by the chairman of the Medway Regatta, Brigadier B. Chichester-Cooke, who said the clubhouse must be "one of the most modern in the country if not in Europe".