There's a secret to the success of the St. Barths Bucket Regatta and it’s probably not what you think. Stunning yachts? Yes. Gorgeous scenery? True. Fiercely competitive sailing? An understatement.

Yet what makes the St. Barths Bucket Regatta the most highly coveted invitation in sailing circles are the demands it places some Type-As with pockets deep enough to always get their way. The mandate: Bring your multimillion-dollar yacht, and your handpicked sailors, but if you’re not coming to have a great time, stay home!

Setting the stage for all future Bucket endeavors, the first regatta came about after a night of inebriated celebration in Nantucket, Massachusetts, in August 1986. Roger Janes, captain of the 82- foot Huisman ketch Volordor, Peter Goldstein, owner and captain of the 65-foot Derecktor sloop Flying Goose; and John Clyde Smith, captain of the 92-foot Bill Garden-designed sloop Mandalay were enthusiastically toasting Mandalay owner Nelson Doubleday’s birthday. Naturally, some trash-talking occurred, some boasts were floated, and the nautical gauntlet was thrown down. The next day, history was made as seven yachts sailed the first Nantucket Bucket, a 15-mile course around Nantucket Sound.