The Regatta was initiated eight years ago as a fun event to celebrate and coincide with Antigua Sailing Week in the Caribbean. Amazingly, through a Google alert, reports of the Regatta came to the attention of the Antigua Sailing Week Race Committee and the Antigua & Barbuda Tourism Authority, who were so impressed with the initiative that they kindly offered to come on-board as event sponsors.

With the Tourism Authority's generous support, the Regatta has become the highlight of SESCA's sailing calendar. After a couple of years of particularly chilly weather, the event was moved from April to June, which has generally provided somewhat warmer conditions.

Antigua Sailing Week , which was regrettably been cancelled last year due to the Covid pandemic, is scheduled to be held from 30 April - 6 May.