Triple Jack’s Latest Round Tortola Record Attempt Raises Money For Humane Society

On Saturday November 18, Triple Jack, the phoenix-like Kelsall 47 trimaran built in 1979, attempted to beat her Round Tortola record of 2:33:33 she set in 2015.  With rare and brisk southerly winds, and a new a sail inventory, conditions looked good for the record-breaking attempt.


Clocking speeds in the mid to high teens, and having completed just one tack and one gybe through the whole route they crossed the line with a time of 2 hours 40 minutes and 4 seconds – just 6 minutes and 37 seconds shy of their 2015 record.


“Triple Jack is in practice mode for a potential Caribbean 600 entry next February,” said Richard Wooldridge, co-skipper/owner with Steve Davis. “After a 6-year refit post Irma we are evaluating to see if she has still got it.”

However, following the valiant but failed attempt the BVI Humane Society is $700 better off. Triple Jack’s attempt was part of the Nanny Cay Challenge in which yachts, kiteboarders, and paddleboarders visiting the British Virgin Islands are invited to make an attempt to beat the latest round Tortola records.  The notional entry fee is a $250 donation to BVI charity of choice.  For this attempt, Triple Jack donated $350 and Nanny Cay matched the donation.

“We will keep supporting the Humane Society until they have their new premises! They go above and beyond looking after some of the most unfortunate animals on the island,” Richard added.

To date $2,700 has been raised for BVI charities:

BVI Humane Society: $700, Triple Jack & Nanny Cay – November 2023
Family Support Network: $250, Mike Hirst – January 2019
BVI Humane Society: $250, Triple Jack – April 2015
RBVIYC Youth Sailing Programme: $250, SPOOKIE – March 2016
RBVIYC Youth Sailing Programme: $250, Aiyana – March 2013
VISAR: $250, Aiyana – March 2013
KATS: $250, INTAC – November 2012
BVI Humane Society: $250, Triple Jack – October 2012
BVI Humane Society $250, Soma – April 2010

“It’s fun way to raise money for charity,” said Miles Sutherland Pilch, general manager of Nanny Cay. “The Nanny Cay Challenge has been exciting to watch over the years, and we’re looking forward to seeing more attempts as the margins get narrower!”

Nanny Cay launched the Nanny Cay Challenge for the round Tortola record in 2010 with Triple Jack’s benchmark time of 3:33:00.  It’s an all-comer, any-day event, starting and finishing off Nanny Cay.  Competitors (except paddboarders) must attempt the record anti-clockwise and round Beef Island, Scrub Island, Great Camanoe and Guana Island to port.  The start transit is in line with the western tip of Peter Island and the western tip of Nanny Cay. 

In addition to the substantial bragging rights, record breakers receive a crew dinner at PegLegs for up to 15 crew members; large bottle of Drappier champagne; and name on the perpetual trophy in Peg Legs.

The record has been broken many times since it was set, but the 2019 Round Tortola Race in the Sailing Festival, the three-day warm up event for the BVI Spring Regatta, was a banner year for breaking, if not smashing,  the record.

A perfect day for record setting saw Fujin, the Bieker 53 catamaran owned and skippered by Greg Slyngstad, win the Nanny Cay Challenge with the fastest elapsed time of 1:57:16, breaking the standing multihull record set in 2015 by the trimaran Triple Jack of 2:33:40 – and the outright record of 2:14:54 set by Mike Hirst on a kiteboard in January that year.   The monohull record was also overturned by E1, the Volvo 70 skippered by Rafal Sawicki in an elapsed time of 2:53:08, beating the previous record of 3:08:43. set in 2016 by the TP52 Spookie.

Gunboat 62 Mach Schnell, owned and skippered by Kent Haeger also broke Triple Jack’s record with 2:00:39; the Rapido 60 trimaran owned and skippered by Steve Bourne did the same finishing in 2:19:54.