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.

The course record was set for 2 days, 24 minutes and culminates in 42 more seconds which was completed by a maxi boat designed by Reichel and Pugh. This year the edition includes a vessel design MOD70 which team Argo is sailing and they are hoping that the weather conditions would hold for them to be able to break it.
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