Things to do in St. John, USVI - Insider's Guide

Tag: Paddleboard


Painkiller Cup 2016

Get ready for the 2016 Painkiller Cup Paddleboard race. The Caribbean’s most exciting SUP event offering $10,000 in prize money!

The 2016 Painkiller Cup will take place on Saturday, January 23rd. The race, a 14-mile downwind run from Trellis Bay to the famous Soggy Dollar Bar on Jost Van Dyke, is open to any team comprising three racers, at least one of which must be female.

The Painkiller Cup is sponsored by the Soggy Dollar Bar, HIHO, The Moorings and Ocean Potion. The event offers $10,000 in prize money with the winning team earning $5,000!

Painkiller CUP 2016 on Facebook:

Painkiller Cup Website

Need Carbon Raceboards or an escort boat?

Contact SUP-St. John / Rockhoppin


Go for a nightpaddle on St. John

You have been on St. John for a while and checked all the basics of your bucket list, like Peace HillCaneel Hill Trail, Annaberg Sugar Plantation, Reef Bay Hike….. and are looking for a new adventure?


2015 Paddle in the Park SUP Race

Celebrating the beaches and waters of Virgin Islands National Park, the Friends of Virgin islands National Park is pleased to again host Paddle the Park, a standup paddleboard race. This year’s date will be NOVEMBER 1st, 2015!

Paddle the Park SUP PADDLEBOARD RACE 2015

will be held on Sunday, November 1st, 2015 at Maho Bay on St. John. More information is here


Paddle the Park SUP Race St. John 2014

Celebrating the beaches and waters of Virgin Islands National Park, the Friends of Virgin islands National Park is pleased to host the 2nd Annual Paddle the Park, a standup paddleboard race. Below is some general information about the race.

Paddle the Park will be held on Sunday, November 2nd, 2014 at Maho Bay on St. John.

  • Short Course from Maho Beach to the NPS floating fee station and back – about 1 mile
  • Open Course from Maho Beach to Whistling Cay and back – about 3 miles
  • Elite Course from Maho Beach to Whistling Cay, then to and around Cinnamon Cay, back behind Whistling Cay and back to Maho – about 5.5 miles

More information the Race including great animated race maps can be found on You can also rent your board for the race with them!


Chaotic Kayak, St. John

SUNDAY, JULY 27th, 2014. The island community of St. John will be out again in force this year to support TRR’s 2014 Wounded Veterans USVI program fundraiser. In 2013 a total of 32 teams took part in what was the 2nd annual St. John Chaotic Kayak race on Oppenheimer Beach. 100% of the proceeds will be used to bring wounded veterans down island every November for one week of healing in the beautiful waters of St. John

It has historically been a fun Kayak race, but they added a SUP race in 2013 and it was great fun. This year’s event will again include a Stand Up Paddle Board race! Bring your own board and entry fee is only $25 per board. If you are a stand up paddle boarder, please help spread the word about this epic event! It’s a really easy race, anyone can do! So come and give it a try!

Need a board for the race? SUP-Stjohn can help you out with one!

Team River Runner (TRR) was founded at Walter Reed Army Medical Center in 2004 by Washington, D.C. area kayak enthusiast Joe Mornini who has been hosting trips for TRR members to St. John since 2007. While the group was forced to cancel its 2008 trip due to lack of funds, that will never be the case again with the continual support of the St John community. Team River Runner is a 501(c)3 non-profit organization. ALL DONATIONS ARE TAX DEDUCTIBLE.

Please join us for our 3rd Annual St. John Chaotic Kayak on Sunday, July 27, 2014. Aside from the SUP and Kayak race, there will be live music, beer tents, food, raffle prizes and more!

For more event details, go to: and


Paddleboard to Salomon Beach

If you’re a free, active spirit , and would rather not use a car to get to the beach, but don’t fancy a mile-long hike then a paddle to Salomon beach might be for you.

Powered by WordPress & Theme by Anders Norén