Friends of the man - unaware of the sex charges - say he was a highly intelligent man and a careful planner with a life-long dedication to bucking authority.
"He wasn't the sort of guy who would take a risk he wasn't sure of," said the owner of the yacht.
The man, who used the assumed name Gavin Maitland when he arrived at Rarotonga, had been expected to buy the yacht which he later sailed to the Cook Islands.
The yacht owner said the deal had evolved over two years and required "Maitland" to pay $20,000 for the yacht Sojourn out of the sale of his unit in the Auckland suburb of Henderson. The unit was listed for $195,000 and sold in early November.
"Maitland" was meant to use the money to settle the yacht purchase by December 20. When the owner went looking for him, he found "Maitland" and the yacht long gone. He reported it stolen.
Rarotonga harbour master Captain John Cornwell welcomed the yacht, which carried no obvious name, on December 31. "Maitland" introduced himself with his false name, saying he had left New Zealand on November 19.
"I said 'what on earth are you doing in a yacht out in the middle of cyclone season ... you must be crazy'."
Cornwell said the arrival in the harbour was unusual. "Maitland" had sailed into the harbour in contravention of the rule which insists yachties call 24 hours ahead to arrange customs and immigration services.
Cornwell confronted him over the lack of warning which "Maitland" said was necessary. "He said he thought he was having a heart attack."
While waiting for a truck to ferry him to hospital, "Maitland" explained he couldn't produce passport or papers because they had been swept overboard.
"Maitland" told the harbour master he was only stopping off on the way to Tahiti before sailing past Pitcairn to Rio de Janeiro in Brazil.
"Maitland" returned from hospital saying doctors had confirmed heart trouble. He visited the hospital again on January 1, catching a taxi to an internet cafe before sailing.
Oddly - and honestly - "Maitland" was back on January 2 with money he had forgotten to pay the taxi driver. And then, he was gone again.
At 9.14am on January 3, "Maitland" radioed for help, saying he was having trouble breathing. Two hours later, authorities couldn't raise "Maitland" so sent a patrol boat with a doctor and nurse. They found the yacht abandoned and empty.
Cornwell said "Maitland" had since been reported seen on Rarotonga. There was a reported sighting on January 5 - two days after he was believed to have gone missing.
"If someone had a jet ski, they could have whipped out, picked him up and been back within an hour."
Inspector John Strickland said an ocean search turned up only a raincoat - originally thought to be a lifejacket. The yacht was returned to Rarotonga when it was searched and fingerprinted by police.
Strickland said it was possible "Maitland" had fallen in and become lost. But another sighting had also emerged - although this one suggested "Maitland" had somehow sneaked onto Rarotonga on December 29, two days before entering the harbour.
Asked if they were searching Rarotonga for the missing man, Strickland said: "I will not comment on that at this time."