This year sees the 34th edition of Pineapple Cup set into operation. This is one of the oldest races that has been going on and sees world-class sailors coming in to participate in every edition. 2019 sees 14 teams participating this time. The race takes place around Montego Bay and it is a biennial race comprising of 811 nautical miles. This is considered one of the oldest races and the celebrated trophy has been given out from 1961. The trophy is a handcrafted treasure that is brought down from London. It has gone to several famous sailors such as Ted Turner, Robert F Johnson and John Kilroy.