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Nine Things I Learned When I Became a Honeymoon Planner for Billionaires

Postnuptial planning can be as dramatic as the big day itself.


Read when you’ve got time to spare.


Illustrations by Zohar Lazar.

Lining up a dream postnuptial vacation can be just as high-stakes as planning the big day itself. (Remember Prince Harry and Meghan Markle’s widely publicized indecision: Was it Africa or Canada?) It can be especially complicated, it turns out, if you are a billionaire. 

Nobody knows that better than the planning team at Ovation Vacations, a leisure travel consultancy for ultrahigh-net-worth individuals. (Think media moguls, real estate tycoons, financiers, movie stars, talk show hosts, and pro athletes.) The company’s team of 30 agents plans more than 200 honeymoons a year, at an average of $50,000 per trip. That’s almost $1 million in honeymoon bookings each month.

Ovation’s president, Jack Ezon, is like the Olivia Pope of travel, handling myriad client requests from the practical to the absurd. And as I learned during a consulting crash course with Ezon and his team, there are many odd asks from the world’s richest honeymooners. By the end of my second day, I had arranged a couple’s hard-to-get dinner reservation at Sukiyabashi Jiro (of Jiro Dreams of Sushi fame), booked a private meet-and-greet with the pope (for a Jewish man, no less), and helped organize a transatlantic charter flight for a sheik’s bird.

But wait, there’s more …

Someone Has to Carry the Meat

After signing a nondisclosure agreement, your first rite of passage with Ovation is to travel with the meat. Literally. The agency’s clients include many kosher and halal travelers (along with plenty of otherwise picky eaters), and one of the most common requests Ovation fields is to have specific cuts of beef flown from a client’s butcher in the U.S. to a location on the other side of the globe.

The title of T-bone chaperone always goes to the agency’s most junior planner. It’s their unenviable task to lug the filet mignons through airport security in chilled briefcases, then onto a commercial jet and eventually to their desired hotel kitchen. Cooking the meat can be an exacting science, too: One planner, Amy, has received paint swatches in the mail from a traveler showing precisely how medium-rare he wanted his steak.

Food requests go far beyond shuttling rib-eye. On my second day at the office I processed a request from a new client who wanted his al dente pasta boiled for an exact number of minutes. And one pop star client fulfilled the stereotype by requesting freshly picked dragonfruit every morning for her daily “pink drink” smoothie … in Iceland. The local authority had strict regulations against the importation of exotic produce, so Ezon had to volley test fruits with the Icelandic government for weeks before securing customs approval.

Celebrities Aren’t the Only Ones With a Dreaded Rider 

Riders are compiled for every one of Ovation’s honeymooners; often they’re so complex, they make J. Lo seem easygoing for wanting the green M&Ms picked out of her candy bowl.

On the manageable end, particularities range from specific plies of toilet paper to strange bed-making methods (two top sheets, with the duvet covering only the bottom half of the mattress, for example). One newlywed visiting the Seychelles would drink only Fiji water; a crate was duly flown in to supply her nightly. Another wanted Elchim hair dryers everywhere she went—including far-flung Laos and Sri Lanka. Once, Ezon was provided with a typed list of 16 condom types a new husband wanted stocked in his minibar. 

Sometimes the requests are so massive in scope that construction crews need to get involved. For a five-night trip, one prominent television actress paid $40,000 to have her hotel bathroom’s granite sink lifted 7 inches higher—all so she wouldn’t have to bend over when washing her face. Similarly, a husband recently spent $80,000 to have a 210-foot yacht completely carpeted, so his new wife could wear her stilettos on board instead of having to—gasp!—go barefoot.

Sometimes You’ve Got to Build the Beach

Why customize the perfect hotel room if you can’t do the same for the beach? That’s what Ezon’s team did when one couple’s dream Caribbean vacation—in a presidential villa with a small private beach—was nearly destroyed by a storm that permanently washed away the seafront. The planning team’s quick solution? Hiring a motorcade of dump trucks to move sand in from another part of the island. It cost a cool $50,000.

Sometimes the solution isn’t quite so extreme. One agent, Christiana, recently traveled to St. Lucia to personally guarantee a picky couple’s beach bliss. The resort had a strict first-come policy for use of their chaise lounges, and refused the client’s offer to buy the entire beach (yes, you read that correctly). So Christiana checked in to the resort herself and claimed the best beachside seats for them before sunrise each morning.

Most Wishes Can Be Granted … Except If They’ll Land You in Jail

“We’ll do anything for our clients as long as it’s legal in the country they’re visiting,” says Ezon, who has fielded only one request for a prostitute in his 18 years of honeymoon planning. (We’ll get to that story shortly.) There have been asks for cocaine and even money laundering—which are both a hard no—but most of the boundary-pushing demands tend to revolve around exclusive experiences. Tickets to the Vanity Fair Oscars after-party are low-hanging fruit. More impressive, Ezon has organized an overnight at Versailles for honeymooners who wanted to sleep in King Louis XIV’s bed. Another time, he arranged a meet-and-greet with Vladimir Putin (no Trumps were involved). Within two hours of joining the agent team, I was on the phone with the Vatican, sorting out the logistics of having the pope marry an interfaith couple on their elopement-cum-honeymoon.

There Is Crisis Management, Around the Clock

Two consultants are on call for every trip to ensure that travelers get a near-instantaneous response to any on-the-ground emergency—a service that about 80 percent of Ovation’s travelers use. Typical on-the-road requests range from restaurant reservation alterations to complete itinerary overhauls; maybe the forecast in Hawaii calls for eight days of rain.

But sometimes trips go wildly awry, like when a couple in Paris got stuck behind a car accident on the way to the airport. Ezon immediately arranged for four motorbikes to pick them up in the middle of the highway (two for the travelers, two for their luggage) and zip them between gridlocked vehicles to make their flight. 

Sometimes a hurricane blows through, or a bride trips and falls on her private jet to Miami and chips a tooth. In the latter case, by the time her plane had landed, Amy had booked a cosmetic dentist—and not the one recommended by the bride’s high-end hotel, who turned out to be a registered sex offender.

“Emergency” can be a relative word, though. One recent newlywed who unexpectedly needed to re-up her supply of feminine hygiene products was too embarrassed to tell her husband or the front desk of her hotel. So the planning team had an on-the-ground contact visit a local bakery and stuff the goods inside a baguette that was delivered directly to her room. 

Some Honeymooners Are Good at Finding Their Own Trouble

There have, perhaps predictably, been instances of the honeymooners getting woefully out of hand. Ezon explains: “At Ovation we adhere to the same credo as Ritz-Carlton: ‘We are ladies and gentlemen serving ladies and gentlemen,’ and there is a line that clients can cross when it comes to gentlemanly behavior.” The wife who hurled dishes at her server when he forgot to bring her Tabasco for her eggs? Yeah, she’s been put on the agency’s very polite blacklist. Racist comments are another hard no-no—as is making a pass at a spa therapist, even if you don’t bellow “Don’t you know who I am?” when she rebuffs.

And Sometimes It’s Trouble in Paradise

Remember when Britney Spears married and divorced Jason Alexander within 55 hours? Some of Ezon’s clients have had their marriages go bust even faster. Just 36 hours into their Maldives honeymoon, one of Ezon’s couples decided to call it off—turns out he hadn’t cut some illicit habits, as promised. The bride was flown out in a jiff. As for the groom? He stayed and requested some professional “company.” Escorting is strictly illegal in the island nation, so Ovation put him on a four-hour flight to Bangkok and set him up with a “nightlife guide” instead.

Another time, a wife rang Ovation to add her hairdresser to the upcoming trip roster, so she could look photo-ready on a series of big nights out. But after Ezon arranged the ticket and hotel room, he received a call from the husband requesting that the extra booking be canceled. As it turned out, he was having an affair with his wife’s stylist … Fredrick. (And yes, the honeymoon went on as planned.)

Three’s Not a Crowd

Asking your hair stylist along on a trip is nothing out of the ordinary for Ovation’s clients—many request the presence of their most trusted helpers, even on a honeymoon. To some high-profile travelers, it’s not privacy unless it’s shared with a security detail to keep the paparazzi at bay; others just like having their housekeepers, makeup artists, trainers, and personal chefs around. One couple paid $2,250 per day to accommodate a trio of German clinicians who could administer intravenous vitamin B-12 solutions to cure their Champagne hangovers.

Sometimes those extra travelers aren’t even human. Honeymooners who can’t live (for five days) without their dogs have been known to splurge on suites with extra bedrooms, massages, gourmet food, and even custom-built hotel furniture. As for the second-most common companion creature? Falcons. Christiana has booked several birds of prey on long-haul flights—they’re allowed on Emirates and Etihad without a handler, she says, as long as you book them a $21,055 first-class suite. “If you put a cloth over their heads, they remain docile for the journey,” Christiana added.

Adding Up the Tab

Ovation has a honeymoon minimum of $20,000, though prices quickly escalate into six figures—especially as private flights are added to the mix. On average, clients spend $1,950 a night for their accommodation, and trips last 2.78 weeks. (Ezon says a large majority stay connected to work while on vacation.)

Among the most expensive trips the team has recently planned? A monthlong private yacht adventure through Africa and the Maldives for a high-profile wife and her billionaire husband totaling more than $1,850,000; a 45-day tour of Oceania, Southeast Asia, and the Med for members of a royal family priced at $1,625,900; and 10 days in Sardinia where the accommodations alone cost $250,000.

Ezon’s hard work doesn’t go unnoticed either—tips have ranged from Bottega Veneta swag and Hermès cuffs to cases of Tuscan wine and checks for more than $100,000.

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This post originally appeared on Bloomberg and was published July 2, 2018. This article is republished here with permission.

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