January 17th, the 2026 Painkiller Cup stand-up paddle competition

Scheduled for January 17th, the 2026 Painkiller Cup stand-up paddle competition offers great competition in two race formats. Racers can choose the 14-mile team race, which starts in Trellis Bay, Beef Island and finishes at White Bay, Jost Van Dyke or the smaller 2.5 mile Mini-Painkiller Cup event from Sandy Cay to White Bay.

The Team race may be arduous. While paddlers rotate every 25-minutes, the conditions can sometimes be rough or windy. But the challenge of racing down Tortola’s beautiful North Shore is second to none!

The Mini-Painkiller Cup is easier and a more attainable challenge. Many intermediate (and sometimes beginner) paddlers join this race. It’s a 60-90-minute paddle for most participants!

Competitors in the team race will compete for $4,000 in prize money and trophies, while the mini racers will compete for trophies and prizes. First place for the winning team is $1,600!

The team race comprises 3-paddlers who rotate every 25-mins on a pre-determined schedule. Start time for the Team race is 10:00am at Trellis Bay. Meet at 9:30 to collect race jerseys and rules briefing. The race starts off the point on the East side of bay. Registration is aboard the race committee boat that will be anchored nearby.

The finish is in front of Hendo’s Hideout at White Bay, Jost Van Dyke.

Please note the former rule that required each team to include a female paddler is no longer in effect.

The Mini-Painkiller Cup starts after 11:30. Final registration on the beach at Sandy Cay where racers get their race jerseys and a quick rules briefing.

The Mini-Painkiller Cup caters to almost any paddler. The first part of the race can be a bit choppy, but then the course smooths out as the fleet paddles down the coast of Jost Van Dyke.

The Mini-Painkiller Cup also finishes in front of Hendo’s Hideout on White Bay.

Please note that the organizers will assist the Mini-Painkiller Cup racers by providing transport from Tortola to Sandy Cay, and back from White Bay. Please follow our Instagram for more info.

Prize Money for the Team Race

• 1st – $1,600
• 2nd – $1,000
• 3rd – $700
• 4th – $450
• 5th – $250

Trophies: The top three teams earn trophies.

Mini-Painkiller Cup

Trophies are presented to the top 10 finishers.

In addition, the top 3 women finishers will be recognized.

In 2026, we will also recognize the top finishing junior paddler.