Get ready for the Caribbean’s best SUP event! The annual Painkiller Cup is scheduled for January 2025. Racers can choose between two events: 14-mile downwind team race with $4,000 prize money; and the 2.5 Mini-Painkiller Cup solo race. Both races finish at beautiful White Bay on Jost Van Dyke where you can enjoy lunch and chill out at Hendo’s Hideout.