Indomitable Strength of BVI’s – 2018 Painkiller Cup by Jeramie Vaine

painkiller cup British Virgin Islands Jost van Dyke
painkiller cup British Virgin Islands Jost van Dyke
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At Standup Journal, we’ve been keeping tabs on our brothers and sisters who have been effected by last season’s hurricanes in the Caribbean.  From the Rincon Beach Boy in Puerto Rico, to the Painkiller Cup in the British Virgin Islands, we are sending so much good cheer and support to our peeps digging their way out from disaster.  Such. Deep. Respect.

Andy Morrell of the Painkiller Cup was the first head up after the storm to say that they would be holding their event no matter what.  Celebrating the beauty and tenacity of the BVI’s the 2018 Painkiller Cup roared off the start line on January 20th to blue skies and epic weather.

Jeramie Vaine and pals were there to tell the tale.

Photo by Jim Scheiner Painkiller Cup
At the finish of the Painkiller Cup, racers are greeted with the cheers of friends & competitors alike and slide into evening with the island’s most famous drink, the Painkiller. Photo by Jim Scheiner

2018 Painkiller Cup delivers the goods in BVIs
Written by Jeramie Vaine

Smiling faces and warm sunshine.


As you step out of the plane and onto the tarmac, the greeting is as friendly as Thanksgiving dinner among family and friends. The welcome sets the tone for one of the most memorable experiences.

The Painkiller Cup is a race that hosts two very unique formats and is set in one of the most breathtaking places in the world: the British Virgin Islands.

Painkiller Cup Downwind vantage -
The Painkiller Cup 12-mile downwind race literally crosses the Caribbean Sea as paddlers launch from the island of Tortolla and paddle to Jost Van Dyke. Photo by: Jim Scheiner

What is the Painkiller Cup?

The Painkiller Cup offers two races, a 14-mile team relay and a 3-mile individual race. These two separate events offer paddlers an experience to paddle on top of crystal clear waters which allow a glimpse into the world beneath.  Paddling over this expanse is as if you were seeing the world from behind the glass in an aquarium.

Each race is a point to point. Paddlers begin on land at one venue and race across the Caribbean Sea to the end destination. At the finish, a crowd of friends, families and fellow competitors await, cheering and celebrating each person’s arrival.

Painkiller Cup Dorina
Downwind conditions are optimal for this event as riders ‘catch bumps’ from one island to another. Photo by: Jim Scheiner

Painkiller Team Relay vs. Mini Painkiller

The team relay requires of three paddlers:  one female and two males. Each racer is expected to sprint for 25 minute intervals on the water. Each team is escorted by their own personal support boat. The team relay downwind paddle begins on the island of Tortola in Trellis Bay and heads across the Caribbean to sister island, Jost Van Dyke.

The Mini Painkiller Cup is a 3-mile shorter and individual version of the race. In the Mini, racers paddle just off a small island on Jost Van Dyke and head around the scenic shoreline into White Bay, eventually arriving on the white sands in front of Hendo’s Hideout.

Team BVI flashes their infamous smiles at the end of a 12-mile rallying call for stoke. Photo by: Jim Scheiner

Special Day, Special People at the 2018 Painkiller Cup

This year was my third trip over to the Caribbean to participate.  Once again, the Painkiller Cup and it’s camaraderie delivered the stoke in the most perfect way. My team was participating in the Painkiller Cup, the team relay and my teammates were Bill Kraft and Isabelle Picard of St. Croix.

The conditions that day delivered a fun downwind course. While catching bumps, cheers from my team filled the air, putting the biggest smile on my face.

Team Triple Stoked. Nuff said. Photo by: Jim Scheiner

What Makes this event Special?

In the past years, like the Mini Painkiller, racers were asked to head over to White Bay to complete the race. However this year, to give back to the islands that were ravished by one of the worst hurricane seasons on record, we stopped at Beef Island, the start of the mini Painkiller Cup, and participated in beach clean up.

After the beach clean up, all the other teams began arriving on the island. The Mini Painkiller Cup set off!  The energy was contagious with all of the support boats following the racers and encouraging the paddlers. Some of the the paddlers from the team relay jumped in and paddled alongside them as well!

Painkiller Cup Jeramie Vaine Isabelle Pritchard, Bill Kraft
Winners of the Painkiller Cup this year were Jeramie Vaine, Isabelle Picard and Bill Kraft. This team has been together for three years and this was their first team WIN. Photo by: Jim Scheiner

Everybody’s a winner:  Take home inspiration

Appearing as an armada of boats, we all made our way into White Bay. This is where the community of paddlers came together as a community for the first time. We all got to celebrate a successful crossing and share our stories of our time out on the water.

There was next a delicious meal put together by the team at Hendo’s Hideout. And the evening grew long with everybody sipping on the local inspired, heavenly drink, which wears the race’s name:  a Painkiller.

Painkiller Cup start Jim Scheiner
Sliding across the ocean blue for a 12-mile stoke fest and downwind fun is what the Painkiller Cup offers its racers. An experience to remember! Photo by: Jim Scheiner

Sup Tribe:  It’s about Community

This year’s race was a special one. These islands, both US and British Virgin Islands, took heavy hits from Hurricane Irma and Maria just four months previously. The local community, some whom had just received power while still others remained in the dark attended and participated in this race.  This dedication to the sport and their way of living showed how strong their island community is.

It was inspiring to see so many people overcoming the devastation Mother Nature had sent their way. They were present and supportive and would let nothing stop them from enjoying a day on the water.  Paddlers and people were all doing what they love among new and old friends.

This was the biggest takeaway from the weekend.

By, Jeramie Vaine
Surftech/NSP Team Manager

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Evelyn O'Doherty, editor & publisher of the new Standup Journal 2.0 is a former school teacher gone rogue. She left her career as a teacher in order to spend more time near or on the water after learning to surf turned her life around (upsidedown?). She is a year-round surfer and paddler living on the eastern tip of Long Island in NY who is a certified SUP instructor, seasoned SUP racer and avid longboard surfer. Evelyn was hired as Online Editor to Standup Journal in 2016. Her passion for the project quickly led to her success and eventually taking over the mag herself in Oct. 2018. Today, as editor, publisher and chief bottle washer at Standup Journal, Evelyn keeps her toes wet writing, traveling, paddling, surfing, and learning to foil. You can find her most days paddling out on Gardiner's Bay or surfing Ditch Plains in Montauk, NY.