He was declared bankrupt in the High Court at Auckland 10 days ago over a mountain of debt owed to the Inland Revenue Department and private creditors.

But that didn't stop former richlister David Henderson, 57, heading to Europe for a holiday with girlfriend Alex Scott, 22, where he was this week understood to be cruising the Spanish coast in a superyacht owned by millionaire David Kimpton.

The holiday goes against the conditions of Henderson's bankruptcy, which forbid him from leaving the country without official permission.

The offence carries a potential punishment of up to three years in prison, a fine of $10,000 - or both.

However, Auckland businessman and former bankrupt Pat Rippin, who is a close friend of Henderson, said "life is for living".

"You've got to do what you've got to do and cop the consequences," he said.

Rippin, though, thought it was unlikely that Henderson would wind up in trouble - "when I went bankrupt I was in Fiji beside the pool".

Henderson is best known for the development of Auckland's Princes Wharf - the cluster of white buildings and the boat-shaped five-star Hilton hotel - and his 2005 drug conviction in the same celebrity drug bust that stung Marc Ellis, Josh Kronfeld and Brent Todd.

He was given a suspended sentence for attempting to buy cocaine.

But his success in the business world was marred by a string of failed projects during the recession.

His penthouse apartment, situated atop the Hilton, has been on the market for four years.

Earning the name 'New Zealand's most expensive apartment', the 880sq m property has a capital value of just under $5 million and attracts $130,000 in ground rent each year.

It was unveiled as the model house on Friday night's episode of New Zealand's Next Top Model. The show's publicist, Polly Viccars, would not disclose how much rent Top Model paid, but said contestants were enjoying "one long and extremely fun sleep-over" in the pad, which boasts wrap-around decking and sweeping views across the city and water.

The apartment has hosted many plush parties - including a Cinderella-themed 21st birthday for Scott, Henderson's girlfriend. Henderson gifted her a Mercedes sports car on the occasion.

Rippin said he had fond memories of champagne-fuelled evenings at the apartment.

"I've been to a lot of parties there. They certainly did go all night, they were always well done with no expense spared," he said.

A lavish New Year's Eve celebration was hosted at the pad by former hacker Kim Dotcom, a German national who recently gained New Zealand residency. Guests, including former Auckland mayor John Banks, were treated to a $500,000 fireworks extravaganza over the harbour which was paid for by Dotcom.

But there have been darker moments at the apartment. Three years ago 28-year-old university student Adam Marshall - a friend of one of Henderson's sons - fell to his death after attempting to jump into the Viaduct Harbour from the balcony.