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How to Vacation Like a Real Billionaire

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For two days, I've slept in my own wing of an echoing estate on a billionaire's private island and been rendered helpless by a butler attending to my every need. I've gobbled three-course lunches, guzzled rum cocktails and champagne, worked out solo in a fully equipped gym, bathed in a bathtub the size of a boat, and had a gleaming yacht at my disposal. I've taken sunset dips in the Caribbean—my footsteps quite literally the only ones in the sand. Suddenly, it's hard to imagine not vacationing like this all the time. Dare I say, I'm starting to feel entitled.
I'm in the Caribbean on Calivigny Island, just off the south coast of Grenada, where for $165,000 a night, you and up to 59 of your closest friends can inhabit the personal vacation paradise of a French businessman and his wife, including the 19,000-square-foot main house, two pools, five outdoor hot tubs, four boats, and a 30-person permanent staff.
Though the price may seem a little astonishing, there are quite a few ultra-affluent travelers who can afford it—and their ranks are growing. Last year, more than 2,000 people on earth were worth $1 billion or more, 185 more than in 2011, according to the global research firm WealthX. And that's just the really big bucks. Lower the bar to include people worth $30 million or more—ultra-high-net-worth individuals, as they're now called—and there are 187,000 worldwide. It's no surprise that the vacation budgets of the ultra-affluent are as outsize as their savings accounts: Nearly a quarter of these super-rich spent $50,000 or more on leisure travel in the past 12 months, according to a 2012 report from Spectrem Group, an Illinois consulting firm for the banking and retirement industries. Half of those spent in excess of $100,000.
At its most basic, travel for the super-rich means never having to deal with the petty and not so petty annoyances that the rest of us must contend with on our trips, and enjoying all of the privacy, service, and amenities money can buy. The super-rich expect space—and plenty of it—safely away from the roiling, less fortunate masses. Minions indulge their every whim—no matter how mundane, insane, or logistically outrageous. Bothered by the cloying scent of Easter lilies? They're removed from the entire hotel. Need to book your wife and two mistresses at different hotels so they don't get wind of one another? The agents, hotels, and concierges who cater to the world's wealthiest will make it happen.
"The word no is not part of my vocabulary because the impossible today may be probable tomorrow," says Jody Bear, of New York's Bear & Bear/Tzell, and, along with most of the agents in this story, a Condé Nast Traveler top travel specialist. "Clients have called me from their Paris hotel at 4 a.m. my time to request a late checkout. They've called from Milan to change a hair appointment at the hotel salon, and from Hong Kong to change their breakfast order. With less than 24 hours' notice, I have arranged for a three-star Michelin chef to prepare a special meal on Christmas Day."
Why You Pay What You Pay
After all, if money is no object, then anything is possible. "We'll do anything for a client, as long as it's legal," says Stacy Fischer-Rosenthal of Fischer Travel, a referral-only service with a $100,000 initiation fee (Barbra Streisand is rumored to be a client). One travel agent who requested not to be named recalls carrying $20,000 in tip money on a multiweek overseas trip for a group. The cash came in handy, the agent says, when customs agents needed to expedite the processing of luggage and when she needed to book 40 people into a top restaurant in Cannes during the film festival.
Businesswoman and philanthropist Tatiana Maxwell was in Morocco a few years back with her best girlfriend, on a vacation meticulously arranged by a travel agent who specializes in ultra-high-end trips. The only thing Maxwell missed was her husband. "I probably mentioned to my buddy, 'Oh, I wish Paul were here. That would be great,' " she recalls.
One night, as Maxwell was wandering through the chaotic food stalls of Jamaa el Fna, she heard a familiar voice. "I turn around, and my husband was in one of the stalls with an apron and a spatula," she says. Just to surprise her, the agent had arranged to fly him in for the night from their home in Jackson Hole, Wyoming.
"There are so few times when your real life lives up to a movie or a book or your imagination," Maxwell says. "That, to me, is why you pay what you pay."
The global financial meltdown that has squeezed most people has not led the affluent to rein in their travel spending. In fact, luxury hotel companies are expanding at a record pace to meet demand, particularly in Asia, and Ritz-Carlton just opened its second top-tier Reserve property, in Puerto Rico, with rooms starting at $1,500 a night. The Beverly Hills Hotel recently sacrificed one of its tennis courts to make room for two 1,800-square-foot "presidential bungalows," which go for $18,150 a night each, nearly three times the cost of what was once the hotel's costliest bungalow. "The very wealthy are the least touched by the financial crisis," says Calivigny Island owner Georges Cohen, who has been a billionaire since selling a technology company in 2000. "It's terrible for poor people, but for rich people, the economic crisis doesn't change their way of living."
A Craving for Privacy
At Calivigny, the living is good. Cohen snapped up the 81-acre island when it was little more than a wilderness and, with his wife, spent an estimated $100 million making the place the definition of sumptuous. The island's main residence, humbly named the Beach House, has marble floors, intricately carved wooden doors made in Calivigny's own workshop, and French colonial–style furniture. The home's soaring windows are swathed in tasseled red-and-green iridescent drapes that open and close via remote control. (Full disclosure: Though Condé Nast Traveler does not accept free trips or accommodations, Calivigny's $45,000-per-night rate for one person was prohibitively expensive. In order to report on the experience, the magazine negotiated a rate of $1,000 for the two nights I stayed on the island.)
Over a lunch of steak frites and chocolate mousse served by a butler, Cohen stresses that the lavish island is a private home, one that guests don't have to share with anyone they haven't expressly invited. That includes the Cohens, who winter on the island but make themselves scarce—on their megayacht, at another of their homes, or elsewhere—if they get a reservation. When a group of 30 booked Calivigny in December, the Cohens reserved staterooms for themselves on the Queen Mary 2 for their first commercial cruise. They would see how it went, Cohen tells me, sounding ever so slightly doubtful at the idea of mingling with the masses.
The craving for privacy isn't necessarily snobbery—no, really, say those who work with super-affluent travelers. Issues with security, both from the press and from any potential harm-doers, make certain locations popular with the private-jet set. Think the Arctic, Africa—anyplace unreachable without a helicopter, boat, hydroplane, or all three.
Experts say that there's a significant segment of the super-affluent who want to venture where no one—or at least none of their friends—has gone before. "They want be the first person to come home and say, 'I went to Cartagena before the Gansevoort opened up,' " says Lia Batkin of In the Know Experiences, a New York agency that works with celebrities, Fortune 500 CEOs, and royalty.
Some of the popular destinations of the moment for extraordinarily well-heeled clients are Arctic Lapland in Sweden, the Salar Uyuni salt desert in Bolivia, and the Emerald Coast of Nicaragua. One high-end specialist is taking clients to Afghanistan and Sudan. The taboo nature of these dangerous spots is what's appealing to the ultra-rich, Batkin says. "It's bragging rights, 100 percent." With all the creature comforts, of course.
Wall Street Getaway
Still, plenty of folks, especially old-money types over the age of 60, are content to stick to more conventional hot spots, yachting around the Mediterranean or renting fully staffed villas on Anguilla or St. Barts or in Costa Rica, Italy, or the south of France. For those who want to stay close to Wall Street, there's The Point, once the private vacation retreat of William Avery Rockefeller, nephew of the Standard Oil tycoon. Finished in 1933, the quirky Saranac Lake, New York, getaway features $3,000-a-night rooms and attracts financial types from New York, who can avoid the six-hour drive by hopping aboard a private flight to the nearby Adirondack Regional Airport.
With a comparatively small main lodge and rustic decor (moose heads, faded Oriental rugs), The Point seems the antithesis of Calivigny Island at first glance. Whereas Calivigny brings on the glitz, The Point has a low-key vibe. It offers neither television nor Internet in the ten guest cabins, and cell service is provided, a staff member tells me, by "AT & Tree"—his polite way of saying there pretty much isn't any.
But both The Point and Calivigny are part of the long-standing tradition of exclusive, reclusive hideaways built by the stratospherically rich, and guests at The Point are hardly roughing it. Go on a hike and you'll stumble across a charming cabin in the middle of the woods, with steaming cocoa and a roaring fire waiting just for you. Saturday night dinner is black tie, and guests are seated together, dinner party style, at large tables beautifully set with fine china. Over six courses and four wines, the talk is of private schools, country houses, and philanthropy. It's not a stretch to imagine this same conversation taking place among the Rockefellers and their guests 80 years ago, during the Great Depression, when life was so very sweet for a very fortunate few.
Of course, even hotels that cater mostly to the run-of-the-mill affluent are used to meeting the needs of the super-rich. No request surprises staff at the Beverly Hills Hotel, where one wealthy guest insisted that they speak to his dog in "dog language" ("Woof, woof, woof, woof!") and a European family of four who stayed for a month demanded new bed linens every day. Not just freshly laundered linens but never-before-used. "We had to break out of our stores 90 sets of linens and take a room out of commission to keep them in" so the guests could see the packages of unused sheets, says Edward Mady, the hotel's general manager. Each set had to be pre-washed in a special detergent. "It was a doozy."
Not all requests are pricey: "We have had guests who complained that the lions were keeping them up at night and who asked if we could quiet them down," says Catherine Biggs, of South Africa's upscale Singita safari lodges. "Another guest requested an elephant dung cake—a piece of elephant dung, iced like a normal cake, with candles."
Adventure Seekers
With seemingly every wealthy person claiming a fashionable sensitivity to some food or flower or fabric, demands can go well beyond standard requests for a gluten-free menu or a particular brand of Scotch. At Calivigny Island, where food is flown in from all corners of the earth, the staff test anything that comes from Japan—including the yellowtail sashimi I enjoy one night—with a Geiger counter. And Richard Turen of Churchill & Turen recalls a vegan CEO who insisted that everything he came into contact with be free of animal products—down to the upholstery in his private car.
For those who’ve seen it all, whose rarefied life has left them filled with ennui, money will buy an over-the-top vacation thrill. Part adviser, part psychologist, part concierge, and part event planner, the “bespoke” travel agents who cater to the wealthy create customized one-off itineraries to surprise and delight even the most jaded adventure-seeker. “It’s about making every experience exactly perfect,” says Philippe Brown, founder of Brown & Hudson, an agency in London with clients from the United Kingdom, China, and the United States (Maxwell, whose husband “appeared” in Marrakech, is one). It might be a private fireworks show, or a balloon trip over the Arctic to view polar bears, arranged by Toronto-based Arctic Kingdom Polar Expeditions.
Perhaps you’d like to be a fly on the wall at an event few outsiders ever get to see. For one $1.5 million family trip to Burma, Based on a True Story, a travel company that specializes in creating over-the-top trips, arranged for its clients to visit a traditional Buddhist monastery for a catered meal and a special blessing by the head monk. Afterward, they took part in an inauguration ceremony for 14 young monks-to-be, featuring a procession of hundreds of elaborately dressed locals, and helped shave the boys’ heads as part of Buddhist religious ritual.
Or perhaps you’d like to take your mingling to the next level by interacting with the local experts Brown calls “influential individuals.” These might be journalists, historians, wine experts, or even more rarefied types. Brown once planned an African honeymoon for a couple who made it clear they were very interested in meeting locals. Brown pressed them for specifics. “I said, ‘Do you mean the colorful Masai, who jump up and down, or Nelson Mandela and Desmond Tutu?’
It was the latter. Mandela, the former South African president, was unavailable, but Brown was able to arrange for the couple to meet Tutu, the Anglican bishop and social rights activist. The price: an undisclosed donation to charity.
Fantasy Story
Then there are the truly outlandish vacations, carefully orchestrated Disneyesque adventure fantasies complete with costumes, sets, and a plot—as close to an out-of-this-world experience as money can buy (until the world’s billionaires can teleport themselves to Mars for the weekend).
Fantasy elements are built into the experience at Musha Cay, a private Bahamian island resort that has hosted Oprah Winfrey, Bill Gates, and Sergei Brin, as well as Saudi and European royalty. The property is owned by David Copperfield, the magician, who carefully manages its many fantastic details and whose unofficial motto for guests is “whatever you dream can happen.”
For $37,000 a night for as many as a dozen people, or $52,000 for the maximum of 24 people, guests can, if they choose, loll in chaises and watch “drive-in” movies on the beach, complete with retro candies and 1950s signage. In another scenario, the Musha Force helicopter lands on the beach, sparking a laser tag extravaganza. If guests happen to leave litter behind, no problem: The island has a team of macaws trained to pick up rubbish and toss it in the trash. “If I can amaze people who have seen it all, it’s pretty cool,” says Copperfield.
Even the macaws are small potatoes, though, compared with some of the trips from Based on a True Story. The company’s founder, Niel Fox, is a British adventurer who made news in 2000 by traveling from the United Kingdom to Antarctica for charity, using only human- or animal-powered transportation (bikes, kayaks, and dogsleds). Along the way, he met some very wealthy people, he says, “and it occurred to me that we could show them the whole world.”
A trademark Based on a True Story trip includes specially built sets—igloos with fur rugs, say, or beautifully furnished fishing huts—multiple destinations, and a script, often designed to appeal particularly to ultra-high-net-worth children. In 2011, the company staged a Christmas trip to the Arctic for a billionaire’s family in which the children helped Santa, who was struggling under the demands of a greedy world. For a Russian family, it created an 11-day pirate vacation that took the group through several countries via camel, yacht, and hot-air balloon and culminated in a pirate battle in Spain.
Morality Tales
And then there were the Children Who Saved Greece, a multimillion-dollar family vacation incorporating input from Europe’s top authority on Greek mythology, the talents of hundreds of costumed actors, and a treasure hunt. “We brought Greek mythology alive,” says Fox. “The children were on a mission to find a massive stash of gold that could help Greece with its problems and restore the Greek gods to power.” They got to keep some of the gold they found—which was real, naturally—but they had to “give” the rest away. The message was, “the kids should be helping, not taking.”
Fox says that he, not his clients, injects the morality in these morality tales. But plenty of ultra-high-net-worth types do try to use over-the-top family vacations to impart life lessons to their children—with mixed results. “There are a lot of blinders on,” says Dr. Jamie Traeger-Muney, a psychologist who consults with financial institutions and individuals about the emotional consequences of wealth. “Often they’re taking the kids to see the other extreme: You go to India and see people living on the street. It really is incumbent on the smart parent not to throw a kid into that environment without having conversations about gratitude, how much luck there is in the world, how much advantage they have by being educated, and the responsibility of having wealth.”
But if the majority of the super-rich are comfortable with this kind of travel, there’s an emerging breed of ultra-high-net-worth traveler who’s younger and newer to wealth and is uncomfortable with excess. This group still prefers to fly below the radar—albeit in first class. At The Point, I met a hedge-fund couple in their early 40s who spoke disparagingly of overly extravagant resorts they’d visited. They looked for places with character, the husband told me, not those that seemed overdone. That sentiment is echoed by friends of mine, a young, retired multimillionaire couple who can’t stomach the economic disparity between those being catered to and those doing the catering.
And call me hopelessly bourgeois, but after two days of lolling around Calivigny, I’m actually yearning to break out of the luxury bubble. My butler boats me to the Grenadian mainland. In St. George’s, the island’s hilly capital, people live in modest homes with goats grazing out front. In 2004, Hurricane Ivan all but wiped out Grenada’s crucial nutmeg industry; the trees are growing back, but for many locals, life is hard. I climb to the top of Fort George, a 300-year-old structure built by the French, a vivacious tour guide named Alice tells me, after they conquered and slaughtered the indigenous Carib and Arawak people and brought in African slaves. When she asks me where I’m staying, I tell her, but, suddenly embarrassed by the revelation, quickly add, “I’m there for work!”
Back on Calivigny, I find myself wondering whether I’d enjoy this life all the time—isolated from the world, secluded from anyone outside my socioeconomic class…unless they work for me. It’s a nice place to visit, I decide, but I wouldn’t want to live here

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