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…