Superyacht Captain Shares ‘Unbelievable’ High Sea Stories

"There is a pride in being witness to some truly unbelievable events – and not sharing their details."

Superyacht Captain Shares ‘Unbelievable’ High Sea Stories

Image Credit: AV Yachts

Superyacht captain Brendan O’Shannassy shares with DMARGE the wildest experiences of his career. From celebrities to wildlife, it’s been an incredible job.

Superyachts are synonymous with excess. They’re known for models, hot tubs, champagne, expensive Monaco moorings, treadmills, zodiacs, helicopters – the list goes on.

But – unless you are part of the 1% – you probably can’t think of too many specific superyacht stories. This is either because the lifestyle isn’t as wild as you think, or because it’s so wild it gets covered up.

Well, fear not: we’re here today to bring you the inside scoop. Here are the wildest superyacht stories we were able to sleuth up. To kick things off, we spoke to Brendan O’Shannassy, a superyacht captain who recently wrote the book Superyacht Captain: Life & Leadership In The World’s Most Incredible Industry.

Brendan told DMARGE exclusively: “It is not the ‘crazy’ antics people might seek. The wildest things relate more to incredible experiences – diving with hundreds of Hammerheads in the Galapagos, swimming with Whale Sharks in The Maldives, and of course… taking Clint Eastwood + Mick Jagger from a function in one of the tenders.”

Brendan added: “I think some of the greatest privileges has been having relaxed and normal conversations with some of the most famous/powerful people in the world. To see that tech founder [such and such] is really just a devoted family person who loves the water and has a really silly side. To listen to a singer, after being pressured by their friends, bang out a tune – no backing/no production – and it be just incredible.”

“To see a world leader listen intently as a 22yr old deck crew member explains their safety obligations to use a Jet Ski.”

Superyacht Captain Brendan O’Shannassy

Brendan refused to be drawn on the wild stories he had heard of occurring on other superyachts (“we tend to keep our own counsel – we don’t share the stories between yachts”) but did reveal that “there is a pride in being witness to some truly unbelievable events – and not sharing their details.”

“I know this is not want people want to read, but ‘keeping the veil in place’ is something we are all very proud of.”  

Superyacht Captain Brendan O’Shannassy

Brendan also told DMARGE that superyacht owners do not see the boundaries that we ’normal-folk’ do. They think differently.

“They probe and challenge all information for its authenticity…regardless of who is saying it,” he told us. “They may not be a subject matter expert, but their questions are disarming as they go from the ground-up…in our normal days we might accept something as fact without fully understanding from a builder, mechanic, even a doctor – the billionaires do not. They will keep going until all facts are clear.”

If that didn’t quench your thirst for gossip, here are another few wild superyacht stories from around the web.

Some billionaires are (accidentally) destroying priceless art with champagne and cereal. That’s right: according to Vox, though it’s not known exactly how, some rich people store priceless art on superyachts as a form of legal tax avoidance. This comes with some problems, however.

As reported by The Cut, a $110.5 million Basquiat (which was on a yacht) once had to be restored after a billionaire’s child destroyed it with cornflakes.

“His kids had thrown their cornflakes at it over breakfast on his yacht because they thought it was scary,” Pandora Mather-Lees, an Oxford-educated art historian and conservator told The Guardian.

“In another incident, a popped Champagne cork struck the canvas of an (unnamed) multi-million-dollar painting,” The Cut reports.

Don’t you hate it when that happens!

Image Credit: Getty Images

Moving on – there are more wild tales to be told. Enter: Marie Claire’s 2020 article: Inside The Sordid World Of Superyachts.

In this article, the author talks about the “golden handcuffs” of working on a superyacht, describing how many crew members are reluctant to speak until they leave the industry, for fear of becoming known as “difficult” to recruitment companies.

The ones who do talk, the author claims, “describe glamorous destinations and large, tax-free pay packets, mixed with long hours, social isolation, sexual harassment and depression.”

One story from that article is as follows:

“Recently, a ‘Mrs’ (shorthand for a boat owner’s wife) woke up on a superyacht in the Caribbean, far from habitation. She wanted 1000 white roses to adorn the craft. The crew arranged for the flowers to be helicoptered from Miami, then brought to the yacht in time for dinner” (Marie Claire).

“The following morning, the Mrs wanted them gone. Unable to throw them into the sea and too far away to drop them at a port, the crew had to jam them into their tiny quarters.”

Chief Stewardess of a Superyacht, Gemma Hulbert, told CNN a similar story of excessive pampering.

Once, she told CNN, a guest only wanted to bathe in half a tub of hot water that was topped off with half a bottle of Fiji water and half a cup of baby oil.

“That was so much fun to clean from the marble after.”


She also told CNN: “I’ve…had a charter guest in the past who purchased a vintage Hermes bag in the States so our purser (the officer on board who keeps the accounts) had to organize a private jet to go to the States from Monaco to pick up the bag and bring it back so she could take it to a gala the next day.”

Crew sometimes see some wild things too. Bloomberg wrote in 2021: “staff see and hear things of a… risqué nature, such as one yachtie whose repeat client insisted on spending her entire seven-day foray in the nude, often passing out drunk in unbecoming positions.”

“Semiclad sunbathing (most often by ‘paid friend’ types), spouse swaps and drunken fisticuffs are also common.”


One yacht captain told Bloomberg: “We’ve seen guys do splits with one foot on the boat and the other on the tender as they drifted apart.”

“One time… we watched someone get slapped in the face by a flying fish.”

Bloomberg also reports that the days when yachts were drifting cocaine dens are over (in the Caribbean at least), writing that boats can be impounded and captains arrested if illegal substances are found on board.

Image Credit: Getty Images

That said, there are still some wild parties (and revenge shopping sprees for irritated partners). According to the outlet, “Often a yacht will be rented for two weeks: the first for the family, the second for bachelor partyesque antics.”

Superyacht staff also speak of cooking elaborate meals for pets, and babies, before blending them to a pulp so that they could be eaten.

South Florida is also, according to Bloomberg, an even wilder version of the Mediterranean.

Bloomberg reports on “time-crunched celebs willing to drop $15,000 on one epic joyride” in which, according to one source, “you head out in the morning, drop anchor at the sandbar off Key Biscayne, play with the toys before you’re too drunk, then dock at the trendiest club.”

“At one club, I was invited on board an owner’s docked boat, only to find a veritable buffet of weed. While looking for the bathroom, I stumbled into another secret lair: a dedicated cocaine room, complete with an ornate mirrored table.”


Finally, how could we forget the hilarious time that news broke of a superyacht crew all dressing in designer clothes, as the owner of their superyacht refused to wear clothes more than once, and so would always throw away his lavish outfits…

There you have it: some of the wildest tales from the high seas.

Read Next