From its casual beginning in Nantucket in 1987 (with seven boats) to its most recent iteration in Newport and St. Barths (where nearly 60 mega-sailing yachts are vying for the right to race), Bucket Regattas have captured sailors’ imagination in a way that no other event can begin to approach.

The first Bucket regatta was organized in Nantucket, Mass, in August, 1986 by Roger Janes, Captain of the 82’ Huisman Ketch, VOLODOR; Peter Goldstein, owner-Captain of the 65’ Derecktor Sloop, FLYING GOOSE, and John Clyde Smith, Captain of the 92’ Bill Garden designed sloop, MANDALAY, to coincide with MANDALAY owner Nelson Doubleday’s birthday celebrations.

During an evening that evolved into a rather torrid Rum Squall, debate raged as to what each yacht and crew could accomplish, and the stage was set for bragging rights. The following day, seven yachts sailed the first Nantucket Bucket, a fifteen mile course in Nantucket Sound. Recollections are hazy as to exactly which yacht won, but records clearly indicate that no yacht finished worse than seventh.

The omnipresent, over riding conundrum for the Bucket Raced Committee is to convince the most competitive owners on planet (demonstrated by the fact that they own these things in the first place) that winning is not that important.