The Painkiller Cup is an amazing downwind SUP Race from Trellis Bay, Beef Island Tortola to Soggy Dollar Bar on Jost van Dyke (both BVI, so you will need a passport to get there from St. John or St. Thomas). Depending on the course you take it is about 14-17 miles. It is a team race for 3 paddlers, that will need an escort boat, share board (14′ and under) and take turns paddling. The prize money is 10.000$ or more ,with 5000$ for the winning team. The 2015 date has just been announced: January 17th. In 2015 there will also be a surfski class.

Painkiller Cup SUP team Race

SUP-Stjohn / Rockhoppin’ Charters has entered a strong team of experienced riders: >For the guys, Patrick (MA) and Mike (SC) who have done the M20, one of the most gruelling ocean races twice and once. The female paddler will be Kim (MA), who has done the 34 mile Cape Cod crossing 4 times. Petra, who has done the Painkiller Cup solo in 2012, won the 2014 Mini Painkiller Cup and circumnavigated St. John, solo and unassisted, will be on our 32FS Regulator which will be the escort boat, trying to help to choose the right course and might decide to hop off the boat at Sandy cay for the Solo race if the team is there on time…..

We are heading from St. John to Tortola Friday night (16th), then to Beef Island Saturday morning for the race which ends at Soggy Dolllar Bar. After the race we will go from Jost van Dyke back to St. John.

Watch the Painkiller Cup SUP Race

Even if you don’t want to race yourself, you can support the riders and cheer for the teams. Either at the start Saturday morning around 10.00 (Trellis Bay, Tortola) or at the finish around noon at Soggy Dollar Bar). Oh and there will be a great pre-race party at The Last Resort on Friday night.

Painkiller Cup Hiho 2015 Paddleboard Race

Mini Painkiller Cup

Not up for the full race and open ocean swells? Try the Mini Painkiller Cup instead, it is a 3 mile paddleboard solo race from Sandy Cay to White Bay.

More information on the Painkiller Cup 2015:

Painkiller Cup Race Format

A team consists of three people and must include at least one female. You will also require an escort boat. Start of the race is at Trellis Bay, Beef Island (Tortola East End). The finish is on the beach in front of  Soggy Dollar Bar on Jost van Dyke.

Board class: You can use any board 14′ and under. Teams must use the same board for the entire race!

In the 2014 Cup, Racers had to switch off their board every 30-minutes. This was mandatory. Racers had to paddle in a rotation that was submitted to the race marshal at the 8:00am registration. There was no need to switch racers at the 30-minute interval once your team has entered White Bay. Each team was free to choose which course they wanted to take, so make sure you have an experienced captain on your escort boat! For the 2015 Painkiller Cup it looks like this is now a 25 minute intervall.


Prize Money:

Minimum $10,000 prize money. The winning team will receive a check over whopping 5000$. The photo below are the 2014 Painkiller Cup winners. For Surf Ski – $2,000 (based on a minimum of 6 racers)


Pain Killer Cup Event Course:


Start is in Trellis Bay, Beef Island. From there you will paddle along the North shore of Tortola, which is relatively protected. After passing Brewers Bay comes the unprotected open ocean leg, where you can expect some big wave and more wind. You will paddle towards Sandy Cay and can either pass it North or South. After crossing the channel between Sandy Cay and Jost van Dyke, it will be more protected again as you paddle along the South Shore of Jost van Dyke and then make a turn right into White Bay for the Soggy Dollar Bar Finish. Stay clear of the reef in White Bay, which will be marked with buoys.



8:00-9:00am at HIHO shop in Trellis Bay 

Racer Meeting

9:00am at HIHO shop in Trellis Bay.

Start Times

SUP: 10:00am; Surf ski: 10:30am (though we reserve the right to change this)

Mini-Painkiller Cup start is at approximately 11:45.  There is no need for mini-competitors to come to Trellis Bay.


Big thanks to the sponsors which make this great event happen! Soggy Dollar Bar, HIHO & The Moorings


2014 Painkiller Cup Results:

Team Race Winners

First place went to Team Tired consisting of Lori Park, Noa Ginelli and Kody Kerbox, of Hawaii, who finished in 2 hours, 30 minutes and 30 seconds. The team also won a $750 bonus for reaching Guana Island first. America’s Cup sailors Jimmy Spithill and Shannon Falcone also competed in the event. They finished in fourth place.

  1. Team Naish (Noa Ginella, Kody Kerbox, Lori Park)
  2. Team BOGA (Nat Ford, Bill Kraft, Isabelle Picard)
  3. Team Caribbean Surf Co. (Colin Butler, Gail Vento, Eric Walker)
  4. Team InterNashional (Shannon Falcone, Paula Lenny, Jimmy Spithill)
  5. Team Riviera (Lee Donovan, Brian Duff, Helga Goebel)

Solo Painkiller Cup Winners

  1. Petra Offermanns, Germany
  2. Sam Morrell, Tortola
  3. Christine Thompson, St. Thomas
  4.  Johnnie Ward, Tortola
  5. Liz Wheeler, Laguna Beach, CA
  6. Tom Wheeler, Laguna Beach, CA

2014 Painkiller Cup Video

2014 Soggy dollar bar, painkiller cup SUP race. 10s clip from A C Q U A F I L M S on Vimeo.

Solo race

Have no team and no boat or want to take it easy? The Mini Painkiller Cup is from Sandy Cay to Soggy Dollar Bar.  The start will be at approximately 11:45. It will be times to start as the lead teams pass Sandy Cay. This course is 3-miles and should take less than one hour. Start is off the beach.
Since the wind and waves are in your back, it is a pretty easy race. Last year some novice paddlers made it to the finish on fun boards. Don’t be shy, give it a try!
There will be plenty of trophies and prizes. Entry fee for the Mini-Painkiller Cup is $50 and includes lunch, race jersey and HIHO clothing.

More information: