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2026 Back to School Regatta & ILCA Masters kick off new sailing season

The 2026 Back to School Regatta and ILCA Masters Championship were held off Nanny Cay on September 19, 2026, and turned out to be a 'glorious start' to the new sailing season. Photo: Royal BVI Yacht Club
Aerin Westlake was the winner in the Optimist fleet. Photo: Royal BVI Yacht Club
Aerin Westlake was the winner in the Optimist fleet. Photo: Royal BVI Yacht Club
There was no competition for the father-daughter team of Gilbo and Zephyr Simpson in the RSFeva category, as only one RSFeva team made it out. Photo: Royal BVI Yacht Club
There was no competition for the father-daughter team of Gilbo and Zephyr Simpson in the RSFeva category, as only one RSFeva team made it out. Photo: Royal BVI Yacht Club
Participants of the Opti Green fleet. from left: Bobby Hensley (1st), Toby Evans, Jervis Tucker-Davis and Sean Stacey. Photo: Royal BVI Yacht Club
Participants of the Opti Green fleet. from left: Bobby Hensley (1st), Toby Evans, Jervis Tucker-Davis and Sean Stacey. Photo: Royal BVI Yacht Club
2nd in ILCA7 & the BVI Masters Champion, Colm Crilly (right). Photo: Royal BVI Yacht Club
2nd in ILCA7 & the BVI Masters Champion, Colm Crilly (right). Photo: Royal BVI Yacht Club
NANNY CAY, VI- The 2026 Back to School Regatta and ILCA Masters Championship were held off Nanny Cay on September 19, 2026, and turned out to be a “glorious start” to the new sailing season.

Racing got underway shortly after 1000 with 9 ILCA 6s & 7s and one RSFeva starting on the trapezoid course. They were closely followed by a fleet of 10 Optimists heading off on the course.

Colm Crilly lifts ILCA 7 Master trophy

In the ILCA fleet, Samuel Allen and Colm Crilly had a few ding-dongs throughout the days of racing and eventually went into the 5th and final race tied on points. After the 30 minutes or so of racing, Samuel managed to pip Colm to the post to claim the Back to School title. Colm, however, was able to win the ILCA 7 Master trophy.

In the same fleet, Ethan George and Thor Downing returned to racing with the club after a few years' absence. Likewise, Richard Brown made his debut with the club dinghy racing and showed great improvement throughout the day.

De Villers wins it all

In the ILCA 6, Emme De Villers clinched the Back to School and the Masters titles after a great 5 races.

It didn’t go all her own way; however, as Kelsie Foley was constantly nipping at her heels. Despite Foley winning 2 of the races, de Villers took the win by two points. Kit Arton also showed great improvement and was up challenging with two second-place finishes to finish third.  Yegâne Güley rounded out the ILCA 6 fleet in fourth place. 

No competition for Gilbo & Zephyr Simpson

There was no competition for the father-daughter team of Gilbo and Zephyr Simpson in the RSFeva category, as only one RSFeva team made it out.

Westlake bows out of Optimist fleet in style

The Optimist fleet had potentially the last appearance of Aerin Westlake and Henry Clifton, who will age out of the class at the end of this year. Both sailors had great races, with Westlake coming out on top in all but one race.

Following closely were Piper Bailey and Arun Bissondutt, who dusted off the summer cobwebs and got their sailing brains in action during the day of racing. Joining the VI sailors after race one was Eden Iversen from St Thomas, who claimed a fourth in Race 4 and finished in fifth overall.

Marked improvement for Hensley

Racing alongside the optimists was the Optimist Green Fleet, and none of the 4 VI sailors was in Optis this time last year. Most impressively, Bobby Hensley, who had only started sailing a year ago, achieved five 1st places in the Opti Green and gave some of the champs fleet a run for their money as well! 

According to the Royal BVI Yacht Club, all of the green fleet gave it their all and were in the mix at the starts and really showed the improvements that they have made through their training.

“We can’t wait to see what Bobby, Sean Stacey, Toby Evans and Jervis Tucker will do in the future.  Serena Iversen from St Thomas joined our green fleet sailors after race one and mixed it up with the BVI sailors. The determination and perseverance of all these sailors really shone through, and they all did brilliantly.”

Results

Opti

1 Aerin Westlake, IVB - 4pts

2 Henry Clifton, IVB - 7pts

3 Piper Bailey, IVB - 13pts

4 Arun Bissoondutt, IVB - 16pts

5 Eden Iversen, ISV - 17pts

Opti Green

1 Bobby Hensley, IVB - 4pts

2 Toby Evans, IVB - 8pts

3 Sean Stacey, IVB - 14pts

4 Serena Iversen, ISV - 15pts

5 Jervis Tucker-Davis, IVB - 16pts

ILCA6

1 Marentia de Villiers (2026 Masters Champion) - 5pts

2 Kelsie Foley - 7pts

3 Kit Arton - 10pts

4 Yegâne Güley - 16pts

ILCA7

1 Sam Allen, 5pts

2 Colm Crilly (2026 Masters Champion) - 6pts

3 Ethan George - 10pts

4 Thor Downing - 16pts

5 Rich Brown - 19pts

RSFeva

1 Gilbo & Zephyr Simpson

2 Jan Alessandrini (DNC)

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