Ocean of Influence: Inside the Celebrity Boat Trip That Was All Over Your Feeds

On the eve of historic legislation that will shower more money on the rich and slash health care for the poor, I find myself on the island of Malta, wandering the ancient walled city of Medina, where the Romans ruled for 600 years before their empire collapsed in a heap of decadence and fire. On the brink of history, I’m sweating out last night’s tequila in a blazing Mediterranean sun, the last traces of a psychedelic compound ebbing in my brain, and wondering how the hell I got here.

I pull up photos from my phone and open a random video: Kate Hudson pole dancing to thumping DJ music as Leonardo DiCaprio bobs to flashing purple lights with his 27-year-old girlfriend, Vogue cover model Vittoria Ceretti.

I wince. It’s all coming back.

I’d just spent the last 48 hours aboard a 790-foot boat with a head-spinning collection of Hollywood actors, models, pop stars, influencers, media moguls, and billionaire entrepreneurs. Our host was billionaire Mark Scheinberg, an Israeli-Canadian who made his fortune building the online poker company PokerStars, which he sold for $4.9 billion. Now, he’s a luxury real estate investor haloed in VIPs.

Ricky Martin and Naomi CampbellSansho Scott/BFA.com/Shutterstock

Scheinberg’s ambition for the trip was simple: to amplify the creamily christened Luminara, the third in a line of luxury ships called The Ritz-Carlton Yacht Collection. This partnership with the hotel chain and Oaktree Capital Management aims to make the super-rich’s yen for superyachting accessible to the merely rich. A bunch of celebrities and influencers would serve as the jewelry glittering like a necklace on Scheinberg’s investment. Perhaps you’ve seen them glittering on your social media feeds, #ritzcarltonyachtcollection.

For reasons that will remain a mystery to me, Vanity Fair was the only publication aboard, given unfettered access with very little by way of guidance. The publicist’s only stipulation—more like a request—is that Scheinberg would “NOT like to be the focus of any press story.”

And so on a hot afternoon, north of Rome, I boarded this svelte, shark-nosed vessel, a petite cruise ship with over 200 staterooms, 5 restaurants, 7 bars, a full-service spa and gym, a discrete shopping mall, and, according to my tour guide, 731 pieces of art curated by a team with offices in Fort Lauderdale and Malta. The guest list was, shall we say, insane: Dakota Johnson, Kendall Jenner, Tom Brady, Orlando Bloom, Pharrell Williams, Martha Stewart, Naomi Campbell, Patrick Schwarzenegger, Ricky Martin, Jaden Smith, Zoey Deutch, Tobey Maguire, Alicia Silverstone, Janelle Monáe, and Sofia Vergara. To name a few. In all, one hundred guests and their entourages, all expenses covered by Scheinberg, including endless food and drink, massages and facials, sound bath healings and yoga classes, Augustinus Bader face creams in every suite, each with a private veranda—a boondoggle to beat all boondoggles. There are three staffers for every guest, “suite ambassadors” and “suite attendants,” who hover outside the cabin doors, eager to iron and rearrange the toiletries just so. The cost of influence—including first-class flights and limousine services to and from the ship and suites and spas and fuel and booze and chefs and staff and flower arrangements, plus a film crew and concert production company—will surely run into the hundreds of thousands of dollars, if not more.

The boat is scheduled to embark from the port city of Civitavecchia at 4 p.m., but it’s already running an hour and a half late. The limos and SUVs have deposited the guests, ushered aboard by an attendant holding an umbrella over everyone’s heads for shade. I’m idling on the front deck with Naomi Campbell and her entourage after enjoying an iced latte with Martha Stewart. Rumor has it that a single guest is holding up the boat. Is it Pharrell, the creative director at Louis Vuitton Men’s, coming in from Jonathan Anderson’s Dior show? Or maybe Tom Brady arriving from Venice with Brooks Nader, who, rumor has it, is his on-again girlfriend?

I’m walking past the Piaget shop when DiCaprio and Ceretti swing around the corner, held up by traffic on the way from the Rome airport. The Titanic star perks up when he runs into two-time Oscar nominee Colman Domingo and his partner, Raúl Domingo. They laugh and embrace, a Hollywood reunion in Italy.

The boat horn blasts and we start to move.

Edgardo Contreras/The Ritz-Carlton Yacht Collection.

Earlier that afternoon, I took a tour through the cool, climate-controlled halls of the Luminara, everything softly lit and walnut-paneled, decorated in creamy leather furniture and black-and-white photographs of oceanic abstractions. There’s a lighthouse lamp that pulses in time to an actual lighthouse on Malta, and there’s a bar with headless statues meant to evoke ancient Greece. The Beach House, a Greek-Egyptian restaurant and bar helmed by Michelin-starred chef Michael Mina, opens to a swimming pool that overlooks the Tyrrhenian Sea. I enjoy a mashed cucumber salad next to the pop star Miguel and Margaret Zhang, the former editor of Vogue China. (Neither will post about Luminara, though Miguel will perform.)

In the evening, the upper decks brim with freshly ornamented guests in “summer chic” attire for cocktails and dinner. Everybody notices everybody else. Who are we? Cards on long, dimly lit tables position the most bold-name faces in close proximity: Leo, Tom, Kendall, Martha, Dakota, Tobey, and Naomi. I am seated near two models, Mary Holland and Sarah Jane Nader. They are soon to appear in a reality TV show on Hulu called Love Thy Nader, produced by Jimmy Kimmel. It’s about four sisters from Louisiana who make their way through New York City and LA, scandalizing their conservative Christian parents with skin-baring photo shoots and high-profile boyfriend hopping. Aspiring Kardashians, one gossip tells me. Sarah Jane, the youngest sister, tells me that when she came out as bisexual to her parents, her mother was none too pleased. I’m told 28-year-old Brooks Nader is poised to be the breakout star (“a mover and shaker, baby,” says Sarah Jane). The striking blonde is a former Sports Illustrated Swimwear model, and rumor has it is dating Brady, whose head I can see across the deck in his new spectacles, a 6’4” librarian. Lauren Sánchez Bezos first noticed Brooks on Instagram and decided to befriend her, Sarah Jane tells me. “Lauren was like, ‘You should hang out while you’re in LA,’ or whatever,” she explains. “And so they got lunch, and they’re very similar. I don’t know how to describe it—like witches, they manifest and get what they want out of life. Powerful women that love supporting other women. They became super close.”

Over the weekend, Sarah Jane broke up with her boyfriend, David Bernad, one of the executive producers of HBO’s The White Lotus. Consequently, Bernad bailed on this cruise. Earlier, I introduced myself to Patrick Schwarzenegger, who stars on the latest season of White Lotus. As we stood by the pool, he sheepishly acknowledged that, yeah, it was a little ironic he was in this glaringly Lotus-like situation, reality and fiction blurring, but what are you gonna do? Heh. Just hope nobody ends up dead in the pool. At dinner, Monáe, who starred in the Knives Out sequel Glass Onion, wherein her character blows up the lair of a narcissistic tech billionaire, was not immune to the irony either. “Is this Glass Onion or what?” she marvels. “Even Kate Hudson’s here!” (Hudson played Birdie Jay, a shallow fashion entrepreneur.)

Orlando Bloom, fresh from his own breakup, comes by our table, bringing Sarah Jane a tequila and lingering with a rakish smile. “We have been friends for a while, and he and his ex just broke up,” she says, swatting away speculation, not naming Katy Perry.

Sarah Jane defends Sanchéz-Bezos, whose wedding ceremony in Venice was fodder for populist outrage, and which Sarah Jane insists was just a normal, plain-Jane affair, nothing fancy. And hey, if the supercouple wanted to blow an estimated $50 million on pajama parties and soap-sudded revels on their yacht, the Koru, then so what. “I guess [Jeff Bezos] is the top of the richest people, but, like, there are a lot of big people where it’s like, yeah, it should be like that,” she says. “He made it fucking big. And, like, they’ve been in love for, like, years or something. They are so secure and real.”

If the press was going to attack her friend as emblematic of the age of oligarchs, well, Sánchez “doesn’t give a fuck; it’s fuel,” says Sarah Jane. “I find that so inspiring.”

And then Ellie Goulding arrives to take the edge off with a song or two. (According to Sarah Jane, Brooks introduced Goulding to Sánchez, which apparently led to Goulding getting the gig at Sánchez’s wedding.) “Who’s in love tonight?” she asks the Luminara crowd as the music stirs to life. She belts her hit, “Love Me Like You Do,” as Kendall, Dakota, and Kate sing along, catching each other’s eyes and laughing like old pals.

As the night wears on, I make my way to the lido deck and pass Leo again, swaying toward the elevator. I can’t shake this guy! A late-night party with Tobey has just dispersed, leaving only a DJ and his girlfriend from Ibiza. As we chat, an astonishing light show suddenly flashes over the wine-dark sea, geometric patterns projected from the boat. It’s 3 a.m. and we’re the only ones who see it.

Zoey DeutchSansho Scott/BFA.com/Shutterstock

The next morning, over breakfast, I meet Rutger, a sales manager for the custom superyacht company, Amels. He tells me the idea for the Ritz-Carlton Yacht Collection originated with a guy named Douglas Prothero, who pitched the luxury hotel chain on a yacht that would motor high-end clientele around the high seas. The Four Seasons had already pioneered a private jet that flies wealthy customers to different Four Seasons locations, White Lotus to White Lotus if you will.

The 2020 pandemic motivated a lot of wealthy people to sequester themselves on boats, thus exposing a whole generation to the joys of isolated pleasure domes. The appeal was obvious: “Say, you want to go to Greece tomorrow,” says Rutger. “You go to Greece.” With crypto and AI cash piling up in recent years, the boats had to be bigger. “That’s a very positive effect,” Rutger says. “But of course, it’s still the ultimate luxury.”

The Luminara is a fantasy of the ultimate luxury, of course, like superyacht LARP-ing. Sitting on the starboard deck, sipping coffee next to the open sea, nobody’s complaining.

On a deck above, I spy Martha Stewart posing for a social media post in a brightly colored SKIMS kaftan. Stewart has arrived with an entourage consisting of her longtime publicist, Susan Magrino, her makeup artist, and her agent. She invites me to lunch at the Beach House, where, while nibbling on plates of Greek delicacies, she tells me a yachting yarn.

It was New Year’s Eve 2003, and she was yachting with her then boyfriend Charles Simonyi, aboard the 232-foot Skat, snugged into a quiet harbor in Malta, en route to the Greek islands. Then, out of the blue, a Naval warship, the USS Donald Cook, pulled in. “They had lost an engine on their way from America to bomb Iraq,” she recounts, “and they were hiding in this little harbor with 26 nuclear warheads onboard in this ship. I did not feel very good about that, but I felt very bad for all the sailors. I handwrote them a note on the very fancy boat stationery, inviting them to come for caviar and champagne and celebrate New Year’s Eve. And so we sent it over by tender to their boat.” (Editor’s note: While the Cook is capable of carrying nuclear warheads, it was carrying Tomahawk cruise missiles at that time.)

The commanding officer and his men motored over in their dress whites and took pictures with Stewart to send home to their wives, as they enjoyed caviar with the greatest hostess in American history. They invited Stewart to tour the battleship, where she saw decks of young “techies” at computer screens. A couple of months later, the Cook was the first to launch missiles into Iraq as part of Operation Iraqi Freedom. “Right at the dawn of devastation,” Stewart marvels. “I hate stuff like that.”

The legendary queen of homemaking, the Joan of Arc of insider trading, Snoop Dogg pal, and getter-of-her-own joke has watched the explosion of wealth over the last 25 years from the decks of many a boat. “I mean, it’s almost common now, extreme wealth,” she says, looking a decade younger than her 84 years. “We know everybody that’s really rich. We know them all. I mean, it started in the 1990s. When I first went public [with Martha Stewart Omnimedia], I was hanging out with Bill Gates and Charles [Simonyi] and the Google boys. I mean, that’s when it started.”

StingSansho Scott/BFA.com/Shutterstock

Back in the day, luxury boating was a rarefied pleasure. “Now everybody has one,” she says. Piles of tech money wrought piles of envy. She once accompanied a boyfriend to Germany to watch his prize be designed and built. “The reason he got yacht envy was when he visited Ron Perlman’s boat, Ultima III. I was on the board of Revlon. The really rich boys started collecting them. It’s penis envy.” (Perlman upgraded to the 280-foot C2, which he later sold.)

Stewart flips through her Instagram feed to find she’s accumulated reams of outraged comments from fans upset by her luxe lifestyle. “Meanwhile people can’t afford food or rent,” writes @sia_next_tuesday.

Her agent leans over and whispers to me, “There’s not a better Instagram follow than @marthastewart48.”

I wonder if the populist comments bother her, what with Zohran Mamdani nominated for mayor in New York City and Donald Trump pushing all the poker chips to the billionaire class. “The Roman Empire coming to an end!” she says.

“I always get that,” she tells me. “I’m mother hen; I’m not supposed to be doing this stuff. I’m supposed to be in the garden picking tomatoes.”

Stewart doesn’t care if rich people enjoy their money “as long as those people are equally generous to people who don’t have anything,” she says. “I’m not ostentatious. I’m sort of frugal. If I were a spendthrift, I wouldn’t be on this boat. I’d have my own boat.”

She describes her time on the Luminara as “working,” not just pleasure cruising. She was invited to host an aperitivo mixer in the afternoon, and the trip conveniently coincided with her European travel plans to see the David Hockney exhibit in Paris and the Caravaggios in Rome. She describes how last Christmas she paid for a private viewing of the Roman Coliseum with her daughter and grandchildren, which included prerecorded crowd noises piped through the speakers to simulate ancient chariot races.

Certainly, the rich have become tackier since her days in the blueblood precincts of Westport, Connecticut, when the wealthy cared about, you know, taste. “My generation, and then the younger generation, were educated in art, collecting art, fine furniture, building very beautiful homes,” she recalls. “The first yachts were really beautiful. The ones that I’ve been on were very beautiful. And now everything is much, much more ostentatious. The art has become all contemporary. Nobody’s collecting. How many Warhols can you have in your house? You know, go into Tommy Hilfiger’s new house in Florida. I mean, it’s so violent. In a very contemporary way, right? The bigger the Warhol, the better, you know? And the colors! It’s nothing like what I grew up with. It is ostentatious, but you sort of envy it, because it’s so fabulous.”

If Stewart has any concern about the new tech-powered billionaire class, it’s not that they’re tacky; it’s that they’re craven in the face of Trump. “Why are they caving?” she asks. “Why are these young, brilliant minds caving to what’s happening in American government? That’s what worries me. I couldn’t care less about what they wear and what they buy and all that other crap. Why are they caving? They don’t want to see their empires crumble, that’s why. And we have a man who’s going to make their empires crumble. We have an emperor that can just go, ‘You! Out!’”

“I’m a great admirer of Elon [Musk] and what he’s done; he’s an inventor,” she continues. “He’s like the Michelangelo [sic, Leonardo Da Vinci] of our time, and look what’s happening to him. Even he is struggling, and there’s very little he can do. Until something big happens. People hate him. I mean, I had to put my Tesla in the garage! And I like my Tesla.”

What kind does she have?

“The fanciest one! Self-driving Tesla! Even my daughter [Alexis] won’t take it. And she’s an environmentalist. She won’t take it.”

Stewart is preparing to write her memoir, which she has already titled Let Me Entertain You. It comes on the heels of the recent Netflix documentary, Martha, which she disliked, criticizing the editing and invasive interviews, and calling the director, R.J. Cutler, “not smart enough.” Her personal archivist is excavating treasures, including letters she wrote during her five-month prison stint for insider trading in 2004. He even found a letter from Jared Kushner. “I was in jail, and his father was in jail, and he was asking how I coped with it,” she says.

“Jail wasn’t so bad,” Stewart observes. “It’s like a long vacation. It was like being on this yacht for five months.”

While we talk, Stewart is charmed by a young model named Miranda Makaroff who is dancing in a pink bikini by the pool to the thump of the DJ from Ibiza, her boyfriend, Pascal Moscheni. “Keep dancing!” Stewart yells to her from the shade of her table. “You’re setting the vibe, girl.”

The pool fills up. Kate. Dakota. Olympic gold medalist snowboarder Shaun White idles under an umbrella. Lithe bodies glisten in the sun. Leo vapes. A music-business personality wades in and discovers a forgotten vial of liquid LSD in the pocket of his swimsuit. “Oh shit!” he laughs, and everyone roars at the thought of the entire pool being dosed. Monáe arrives with her entourage, model-girlfriend Stephanie Silva and producer Nate Wonder, who join the rapper Anderson .Paak and his close pal, actor Jonnie Park. Strawberry daiquiris appear on trays, one round and then another. And then another. A sloshy bonhomie takes hold, and perhaps microdoses of LSD, as the DJ grins and bobs his head. From the pool, Sicily is less an actual place than a landscape painting to gaze upon while luxuriating in a brine of ultrasoft water and SPF 30. No one will set foot on shore.

Our host appears at the edge of the pool in a man-bun and well-conditioned beard, physically fit in a tight T-shirt and short pants, looking less like a 52-year-old billionaire than a deckhand on a St. Barth’s yacht. He beams at his creation as a hired camera crew shoots promotional footage of Silva with a cocktail balanced on her head.

Stewart’s mixer is at 5:30 p.m., and the guests migrate upstairs in “cocktail chic,” as advised by the official itinerary, for “Martha-ritas.” “I want them on the permanent menu on the ship,” Martha tells the chairman of the Ritz-Carlton Group, and he eagerly agrees. White, Ricky Martin, and the foreign minister of Malta line up to kiss Stewart’s ring.

Over a card game called KBÓM, everyone agrees that the mix of guests on board is strange. “Is this real?” the DJ’s girlfriend will later post on Instagram.

More cocktails on the upper deck and another extravagantly appointed dinner amid floral arrangements designed by a Dutch team flown in for the occasion. Sting motors over from Sicily, dressed in a handsome bone-colored linen suit, to perform a dinner set of hits on an acoustic guitar. He introduces each song with a story; for instance, the tale of the prisoner who made a guitar from the planks of a shipwreck of migrant Africans, on which Sting now plays “Message in a Bottle.” At DiCaprio’s behest, the musician dedicates a song to Maguire, who is turning 50. After the show, I wish Maguire a happy birthday and his eyes become wet with tears. His voice cracks as he gushes gratitude for his teenage son, who is standing next to him.

Monáe, in white robot glasses, launches into a DJ set of 1980s bangers on the dinner deck. A swarm of drones is launched, producing a light show in the sky. We watch as the word “Luminara” materializes in sparkling cursive, a luminous brand name blotting out the stars over Sicily. Cameras up! The billionaire smiles from a railing above, a lord on his parapet.

Janelle MonáeSansho Scott/BFA.com/Shutterstock

Even the bartenders are dancing now as they sling tequila. To escape the mob, I wander back to the lido deck and find a small gathering of celebrities. We play a parlor game called “dares or pairs,” in which we choose a number between one and five and shout it simultaneously to see if a dare must be performed. I dare you to lick her nipple. A movie star attends to a tipsy blonde woman; a personal assistant canoodles with a wingman. It’s 3:30 in the morning, and things are getting sloppy.

By 5 a.m., everyone has disappeared, including the staff. I assume someone is up there driving this thing. Unable to sleep, I walk the length of the boat, back and forth, empty deck after empty deck. Vast, luxurious rooms of unpeopled furniture, empty mirrors, vacant staircases, Ileana Makri jewelry gleaming in lit cases, a black horizon visible through floor-to-ceiling windows, the sea sloshing by. From my veranda, I watch the sun rise over Malta, a sandstone horizon of ancient histories: the Phoenicians, the Romans, Saint Paul of Bible fame, the British before their empire faded—all of them here, rising and falling at the crossroads of civilizations. I pack my things and walk down the gangplank to be greeted by an attendant, a sweet Dutch teenager dressed in a neat blue shirt and awkwardly knotted tie, who will help me to one of the limousines lined on shore. He’s working at the port for the summer, a front row seat to the wealth of the world. I see Stewart and her entourage head for their chartered flight to Paris. I point to White coming down the gangplank. He used to be an Olympic athlete, I tell the boy, but now he’s more like an Olympic brand ambassador…

“He makes money,” says the boy, grinning.

He knows the story better than I do.

I flick on my phone to read the headlines: Trump wants to jail Mamdani. A text arrives from the cruise organizer: Please don’t mention [redacted] or [redacted] in the story. I smile, imagining panicked publicists in Los Angeles. Soon, I’ll be told there’s a “wrench in the plans” and I’m “not allowed to proceed” on the story.

I can’t unsee what I saw, of course. And it’s still a free world. Even on dry land. For now.

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