2020 Event Information

Painkiller Cup

Saturday, January 18th, 2020

The 2019 Painkiller Cup will take place on Saturday, January 18th. The race, a 14-mile downwind run from Trellis Bay to White Bay, Jost Van Dyke, is open to any team comprising three racers, at least one of which must be female.

We are expanding the event to include a solo race.  These are three options for competitors:
Team Relay Race, Solo Race & Mini-Painkiller Cup

Race Course

The relay portion of the race starts at Trellis Bay and finishes on the beach in front of Hendo’s Hideout in Great Harbour, Jost Van Dyke. Racers rotate in a predetermined format every 25-minutes. Once a team enters White bay there is no need for a final rotation.

Course & Format

Race Course

The Painkiller Cup race format comprises a 14-mile relay race starting in the shallow water at the top of Trellis Bay and finishing in front of Hendo’s Hideout in White Bay, Jost Van Dyke. The course is down through the narrow body of water between Great Caminoe and Beef Island, then through the Guana Island cut and down the North Shore of Tortola. The course is wide open as the paddlers cross from Tortola to Sandy Cay, which may be passed on either side, before running down the South side of Jost Van Dyke and turning in to White Bay.

The Mini-Painkiller Cup format is simpler. The race starts on or just off the beach on Sandy Cay and finishes at Hendo’s.

Race Format

The Painkiller Cup race starts in shallow water at the mouth of Trellis Bay. SUP racers must switch off their board on a predetermined rotation which is provided to the organizers at registration. The paddle time per racer is 25-minutes. There is no need to switch racers once your team has entered White Bay.

The Mini-Painkiller Cup is a solo race with all paddlers competing together.

SUP Teams

Teams of 3 racers; at least one racer must be female


Any board 14′ and under. Teams must use the same board for the entire race


It is recommended that each SUP team have their own safety boat.


Racers must wear the supplied jersey at all times during the race.