Manly 16ft Skiff Sailing Club traces its roots to 1921, when a group of Delwood Canoe Club members began racing on Sunday afternoons. The club was formally established on 23 February 1923 as the Manly Sailing Club, adopting the 16ft skiff as its class of choice by the mid-1920s. In 1928, the club secured its first lease on the current Manly Cove site and built its first boat shed.

Through the Depression, World War II and beyond, a dedicated core of members kept the club alive. In 1952 it was renamed the Manly 16ft Skiff Sailing Club, and in 1960 obtained its liquor licence - a turning point that funded ongoing improvements to the facilities and the sport.

The following decades brought steady growth in fleet sizes, major renovations to the clubhouse, and championship success across multiple classes. Australian titles have been won by club sailors in 16ft skiffs, Flying Elevens and Manly Juniors, and in 2007/08 all four classes raced at the club won their Australian Championships simultaneously — a feat repeated in 2013/14 and 2015/16.

In 2010, the club amalgamated with St George Sailing Club at Sans Souci, preserving 16ft skiff racing in Sydney's southern suburbs. The St George clubhouse was subsequently demolished and fully rebuilt, reopening in 2022.

Today, with over 11,000 members and two waterfront venues, the club remains as passionate about racing and community as it was over a century ago.