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 2016 date has just been changed to January 23th.


Painkiller Cup 2016 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 interval.

Prize Money Painkiller Cup 2016:

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)


Mini Painkiller Cup 2016

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 2016:

Pain Killer Cup 2016 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.

Painkiller Cup SUP team Race – Looking for Riders

SUP-Stjohn / Rockhoppin’ Charters will again be entering a team and are looking for riders (our 32 FS Regulator will be the escort boat). We will be heading from St. John to Tortola Friday night. After the race on Saturday 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.

START TIMES & OTHER INFO (this is from 2015 but we believe the schedule will be similiar)


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


2015 Painkiller Cup Report 

can be found here

2015 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: