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The origins of the Bermuda Fitted Dinghy date back to the early 1800's. The term “fitted” was a loose term meaning that watermen would take their workboats and would “fit” them from commercial dinghies during the weekdays into sailboats on the weekends. These fishermen and cargo men would add makeshift masts and oversized sails to their small wooden boats.

Using fitted dinghies as race boats evolved throughout the 19th century as a cheaper alternative to expensive yacht racing. As the fitted dinghy evolved, so did the sport of sail racing in Bermuda.

In 1897, Ambrose Gosling designed two fitted dinghies: Contest  (the original) and Nia. These boats were not converted workboats, but specifically designed to race. This was a turning point when Bermuda boats were no longer being made for leisure and work, bur for sport. With the dedication of race boats the Bermuda Fitted Dinghy became a standardized boat with its own class rules specific to the fleet. In the 20th Century Fitted dinghies were owned and raced by syndicates who were members of various private yacht clubs.

Today, the Bermuda Fitted Dinghy is held to the same dimensions and standards set in 1883: 14 feet 1 inch overall wood end to wood end (stem to stern). Other than the size of the physical boat, all other aspects have no limitations: number of crew, size of the mast, boom, sprit and sails including the main, spinnaker and jib. This would explain the beautiful proportion of the large sail area juxtaposed against the small wooden hulls.

The tradition of Bermuda Fitted Dinghy racing has been kept alive as an inter-club activity, fought between the private sailing and boating clubs of Bermuda. Each club has their own fitted dinghy and racing is carried out on set dates in a variety of locations including Hamilton, St. George’s Harbours, Granaway Deep and Mangrove Bay. The class does not race using World Sailing's Racing Rules of Sailing ‚Äč but with its own set of racing rules.

The purpose-built Fitted Dinghy known as “Contest III” has been in the possession of RBYC since 1991. She was designed by Jim Taylor and built in Gloucester, Mass in 1990 by Mark Lindsay. Contest III completed her first full season of dinghy racing in 1992, winning the Coronation Cup for Overall Winner in her Maiden season.  She has won the Heritage Trophy (for the opening race in May)  twenty-one times; more than any other syndicate, including all 11-years of Past Commodore Somers Kempe's tenure as her skipper. Contest III continues to be the pride of the Club, and is actively raced in the Bermuda Fitted Dinghy races held during the summer season. Her crew are known as the 'Contest Warriors'.

Contest III Skippers

  • 1991 - 1992 Hubert Watlington
  • 1993 - 1998 Andreas Lewin
  • 1999 - 2001 Martin Mello
  • 2002 - 2012 P/C Somers W. Kempe
  • 2013 -  Dmitri Stevens
  • 2014 - 2015 Peter Miller
  • 2016 - 2018 Julia Lines
  • 2019 - Present Joshua Greenslade