The two determined to race out to the green buoy and back the next day to prove their mettle. As the evening wore on, weather set in, and the wind was blowing hard. Captain James suggested Goldstein not risk going out to his boat in his dinghy but instead spend the night onboard Volador. The next morning John Clyde-Smith the captain of Nelson Doubleday’s yacht Mandalay popped by and the idea of putting together a friendly race gained steam. Doubleday’s wife’s birthday was coming up, so it was decided to have the race the following weekend, making it an event where the family and crew were one for a weekend. The race was an invitational race, not a professional one. The first year there were 7 or 8 boats, The cost for entering that race was $300.00 a boat. And as it was his wife’s birthday, Doubleday offered to invite all to a celebratory post-race clambake.

The first Bucket was a big success and grew every year. After 15 years, Goldstein who was in charge of all — including engraving winner’s names on the silver trophy purchased by Doubleday at a Nantucket antique emporium — decided they should call it quits while they were ahead. The stakes had become higher, concern for safety, handicap rules and ratings were becoming challenging, and, as Goldstein said, “The boats are getting bigger, and it is all getting too complicated.” Furthermore, there is no room on the trophy for any more names.”

Conventionally, many super sailing yachts summer in New England and the Med but head to the Caribbean in the winter. In 1995, the idea of the St. Barth’s Bucket was conceived by some who had partaken of the Nantucket Bucket. Thereafter, a Newport Bucket took flight. Eventually, the Newport Bucket ran its course and ceased to exist, but the St. Barths Bucket had staying power, and its legend lives on. Royal Huisman is one of its chief supporters.