Known as one of the world’s great ocean races, the biennial Pineapple Cup presents a combination of challenge and reward that attracts top ocean racers time and time again. There is no easing into the 811 mile course; the race starts from Ft. Lauderdale and immediately takes competitors across the Gulfstream, heading East to Great Isaac, the beginning of their trek through the Bahamas. After passing Great Isaac, the fleet will leave Great Stirrup Cay and Eleuthera to starboard, with the turn at Spanish Wells, on the North end of Eleuthera marking the beginning of the work to the South. Peter Bowker, navigator for none other than Ted Turner, quoted his skipper as saying that if you rounded the tip of Eleuthera without bumping the rocks, you were too far offshore. After Eleuthera, the fleet approaches Cat Island with a decision to make. In the last race, PHRF Fleet winner Affinity made nice gains with the bold move to the West of Cat Island, shortening the course a bit, and enjoying flatter water, while the rest of the fleet stayed offshore. Long Island and the Crooked Island Passage are next, followed by the rounding of Cuba, with gains for the daring and penalties for the careless. The rhumb line may go straight from the Eastern tip of Cuba to the finish off of Montego Bay, but the racers might not. The last big tactical decision is whether to work the shore East of Montego Bay, or approach from offshore. Finishers are rewarded with a case of cold Red Stripe Beer, the traditional welcome from the Montego Bay Yacht Club. The winning boat stamps its name on the coveted silver Pineapple Cup.