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Yachts and paddleboarders are invited to make an attempt to beat the latest Round Tortola Record.




Triple Jack
Richard Wooldridge/Steve Davis
April 30, 2015


TP52 SPOOKIE Nanny Cay Cup


Steve & Heidi Benjamin
March 29, 2016




Mike Hirst & Mark Cochrane
September 17, 2014

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Entry fee of $250 donation to BVI charity of choice includes two night’s dockage (before and after attempt) at Nanny Cay.

Charities to benefit so far:

– BVI Humane Society, $250, Triple Jack (April 2015)
– RBVIYC Youth Sailing Programme: $250, SPOOKIE, March 2016; $250, Aiyana, March 2013
– VISAR: Aiyana, $250, March 2013
– KATS: $250, INTAC, November 2012
– BVI Humane Society: $250, Triple Jack (October 2012); $250, Soma (April 2010)


– Perpetual Trophy (on display at Peg Legs)
– Name on Trophy (plaque)
– Crew dinner at PegLegs if record broken for up to 15 crewmembers; does not include alcoholic drinks with the exception of the of champagne.)
– Large bottle of Drappier champagne
– Bragging rights!

Only realistic entrants will be accepted. To enter, contact Miles Sutherland-Pilch, General Manager, Tel: (284) 494 2512,


Aiyana, Alia 82, Peter Corr - March 26, 2013
(Record broken March 2016)


INTAC Mark Plaxton - November 17, 2012
(Record broken March 2013)


Jurakan, Melges 32, Dave West, November 2009
(Record broken November 2012)



Triple Jack, Kelsal 47, Richard Wooldridge, October 2012.
(Record broken April 2015)


Soma, Formula 40, Nils Erickson, April 2010
(Record broken October 2012)


Triple Jack, Kelsal 47, Richard Wooldridge, November 2009.
(Record broken April 2010)




A $250 donation to the BVI charity of your choice if you break the record
Dinner for record-breaker plus 1 at Peg Legs
A bottle of Drappier champagne for each record-breaker
HUGE bragging rights!


Record attempts must be self-supported
A Nanny Cay representative must ratify start and finish times
Nanny Cay reserves the right to reject the attempt for any reason and accepts no responsibility any loss, damage, or injury whatsoever!

Latest Nanny Cay Challenge News

2016: A Look Back

The year ended on a high note, as we opened the new outer marina after 17 months of construction. At a ceremony held at the entrance to the new outer marina on December 12, Premier and Minister of Finance, Dr. the Honourable D. Orlando Smith, OBE, declared the marina officially open.

47th Annual Pegs Legs Round Tortola Race Adds A Twist

The 47th annual Peg Legs Round Tortola Race organised by the Royal BVI Yacht Club (RBVIYC) and sponsored by Nanny Cay, will take place on Saturday, November 19th. Four classes – racing, performance cruising cruising and multihull – will compete in the 37-mile race. The course change for the 2016 race will give competitors more tactical choices to make.

Nanny Cay Challenge Monohull Record Falls To SPOOKIE

Triple Jack takes overall; SPOOKIE breaks Monohill Round Tortola Record; The BVI Sailing Festival Round Tortola Race for the Nanny Cay Cup and Nanny Cay Challenge started promptly at 09:30 on Tuesday morning in seas a little rougher than normal due to last week's high winds, and an easterly breeze of 18+ knots. The BVI-based trimaran Triple Jack, owned by Richard Wooldridge and Steve Davis, charged off the start to an early lead in the CSA Multihull class. She made her way around the island in 3 hours and 19 minutes - almost 46 minutes slower than her record-breaking time last year - but her corrected time of 3:46:38, gave her first place overall in the 2016 Nanny Cay Cup.

Round Tortola Race For Nanny Cay Cup Kicks Off 2016 BVI Spring Regatta

The Round Tortola Race Race for the Nanny Cay Cup kicks off the 2016 BVI Spring Regatta & Sailing Festival tomorrow and life couldn't be more perfect for the crews of 54 boats competing - the forecast is for breeze in the upper teens. The Nanny Cay Cup not only sets the scene for a week of great racing with spectacular views of Tortola throughout the 31-nautical mile race, additionally, the teams can also race for the Nanny Cay Challenge - a perpetual challenge for the fastest mono and catamaran record around the island.

New boats, old boats, all return for spectacular racing At 2016 BVI Spring Regatta

With a different race course every day and guaranteed no-two-days-of-racing-the-same sets BVI Spring Regatta apart from other yacht racing events. Fabulous beach parties every evening are the only way to end a perfect day of warm-water Caribbean racing. With a long-time home base here at Nanny Cay where families can also enjoy all that Tortola and the surrounding islands offer, the event offers something for everyone.

Triple Jack Sets New Round Tortola Record

On Thursday April 30, trimaran Triple Jack and crew managed to take 6 minutes and 38 seconds off their existing Round Tortola record, rounding the island in 2 hours, 33 minutes and 40 seconds. It is Triple Jack’s third Round Tortola Record. Despite high hopes for optimal conditions with 15-20 knot winds from the SSE, winds were lighter than expected. Indeed, the winds softened for the important final leg from Soper’s Hole back to Nanny Cay after some unexpectedly big winds on the north side of Tortola.