This regatta's history dates back to 1986 when seven superyacht owners were celebrating a birthday together in the Massachusetts island of Nantucket. The conversation turned to the relative merits of their craft and their own sailing talents, and it was decided that the matter would be settled the following day out of the waters of Nantucket Sound.
The racing was great and the pontoon party afterwards sealed the deal - this would be an annual event. When the winner asked for a trophy, a handy bucket was presented and the event had its name: The Nantucket Bucket Regatta. The vent moved to the Caribbean island of St Barth in 1995 where it has been raced every March since with a burgeoning fleet of up to 40 sailing superyachts and a sprinkling of sailing's 'rock stars' in the afterguard.