At an inquest in Kaikohe today, Coroner Brandt Shortland was told Mr Waddilove had planned to sail to Australia via Norfolk Island to visit his son.
He had not notified Customs or Immigration and had planned to "fly under the radar", Mr Shortland said.
The last people known to have seen Mr Waddilove were sailors Marion and Stuart McAulay, who met him at Whangaroa Game Fishing Club on New Year's Eve, 2010.
Mr McAulay said the sailor, who had a "Willie Nelson appearance" with silver whiskers, long hair and a bandanna, told him he'd been heading for Houhora so was surprised to find himself at Whangaroa, some 80km to the south.
Mr Waddilove was unconcerned to hear that Norfolk Island had no harbour, saying he'd been a seafarer all his life.
The Boadicea was seen a few days later struggling around Surville Cliffs near North Cape.
A search was mounted after what appeared to be an inflatable tender was seen off Cape Reinga on January 5.
It was spotted by an aircraft, apparently upside-down and deflated, but a boat was unable to find it.
Mr Shortland found that Mr Waddilove likely drowned.