The event that legendary sailing commentator Peter Montgomery called “the best big-boat regatta in New Zealand” will celebrate its milestone 20th anniversary later this month.

With almost 100 entries on the list two weeks out, organisers say this year’s Bay of Islands Sailing Week – which will take place at Ōpua on January 24-27 – was already shaping up to be a competitive and highly enjoyable regatta.

The event had won a loyal following over the years with several names on the 2023 entry list also appearing on the results sheet for the first Bay of Islands Sailing Week in 2003.

While some had missed the odd regatta over the years and others now owned different boats, a few had sailed in every one of the past 19 editions and would compete this year in the same yachts they sailed in 2003.

Cees Romeyn, owner of a Whiting 29 named Nexus, remembered his first Bay of Islands Sailing Week for all the wrong reasons.

“I went the wrong way,” Romeyn said.

“In one of the races everyone started and they were all coming towards me – I came from the other way. So yes, I remember that one very well.”

Fortunately, Romeyn’s sailing skills have improved over the past two decades. From second-to-last overall in the first regatta, he placed a respectable fourth on handicap of 11 boats in the E division during the last regatta in 2021.

Now 80 years old, Romeyn has always staunchly sailed in the windward-leeward E division, going against the grain of the 30-footer (nine-metre) fleet.

He would have done the same this year but was short of experienced crew, so he was planning to compete in the Island Racing division for only the second time in his history at the regatta.

Romeyn said the “marvellous” event was one of the highlights of each year’s sailing calendar.

Nev Campbell, another event veteran, had entered his Atkinson 40 Kantime for the 20th time this year.

He said the appeal of the regatta was not just the quality of the sailing, but also the camaraderie among sailors after racing wrapped up each day.

He was looking forward to both at the forthcoming event.

“I hope it’s as good as all the others, and I hope that as many boats turn up. That’s the main thing.”

Other recognisable names from the first regatta included Ray Haslar, an event founder who was instrumental in its success.

This year Haslar would sail a new boat, a racy nine-metre Soto design named The Muppet Show.

Fellow regatta founders Nina and Tony Kiff had also sailed most of the last 20 regattas on their boat Wetherley, only missing one or two to volunteer behind the scenes instead.

They were recently recognised at the Yachting New Zealand Excellence Awards for their tireless efforts as Sailing Week committee members and volunteers.

■ Entries are still being accepted for the 20th anniversary event. Go to www.bayofislandssailingweek.org.nz for more information and online entry forms.