Mr Montgomery said the regatta's success hinged on the venue - the area between Red Head (Okahu) Island and Ninepin Rock in particular was "like nothing else" - plus the commitment of its volunteer organisers and the quality of the fleet.
Most of the organising was done by a group of about 10 locals, who did it because they wanted to contribute to their community and to sailing. He had been told that if the regatta was organised by paid professionals the fee would between $60,000 and $100,000.
"You don't have a regatta with this commitment and passion in Auckland or Wellington. You've got the best boats and the best sailors here."
Sailing Week was started by Opua couple Tony and Nina Kiff, who wanted to recreate the kind of regatta they had enjoyed at Cowes on the Isle of Wight, in 2003.
Mr Montgomery said Ray and Lesley Haslar later took up the challenge, tapping into members of the local sailing community like Kerikeri's Mike Quilter, who sailed with the late Sir Peter Blake, and had been running it ever since with the help of people like the "chillingly efficient" event administrator Melanie MacDiarmid.
For the second time this year the southern hemisphere's biggest superyacht race, the Millennium Cup, was held alongside Bay of Islands Sailing Week.
Peter Busfield, of the New Zealand Marine Export Group, said the race was moved from Auckland in a bid to rejuvenate the event.
Holding the event outside Auckland also led to greater camaraderie and networking.
When it was held in the big city, sponsors and marine industry staff headed back to their offices once racing was over - but in the Bay of Islands everyone joined in with the post-race Sailing Week social events.
Footage of the event was broadcast and published in specialist magazines worldwide, bringing extra publicity to Northland, he said.
- Mr Montgomery is best remembered for his quote "The America's Cup is now New Zealand's Cup" when Team New Zealand won the America's Cup for the first time in San Diego in 1995. The line has been voted New Zealand's most memorable moment in sporting commentary.