In the era of the humble brag, it’s harder than ever to know how your boss travels. Assuming he or she is the type that likes to share, you might see a suggestion of a private jet or a swanky beach resort on Instagram—or hear one unassuming story about the sea turtles that swam under the paddleboard in St. Barthelemy.
Unfortunately for your water cooler conversations, no chief executive officer is ever going to spill the beans on his favorite private island, the extent of his security detail, or the lengths his assistant went to procure Coke Zero in Madagascar.
For that, we turned to Jaclyn Sienna India, president and founder of the decade-old travel consultancy Sienna Charles. Almost immediately after hanging a shingle on West Palm Beach’s ritzy Worth Avenue in 2008, India got her lucky break: An unexpectedly productive, $25 ad with the Explorer’s Club turned out her first billionaire client, and word of mouth turned one into many.
Now India is a go-to for the finance world’s jet set, regularly organizing trips for at least two dozen CEOs, along with other titans of industry and a handful of former U.S. Presidents. Her clients range from Morgan Stanley higher ups and former top-level executives at American Express, to billionaires and real estate tycoons. Of the hundreds of trips she plans each year, 90 percent are for high-ranking finance types—some with budgets that climb into the millions. Chatting about restaurants, she says, is the best way to let these power brokers know she’s playing on their level.
“People can be all over the map,” she said, explaining that often clients are looking for a vibe or set of experiences rather than an exact destination. To help them wade through their options, she prefers face-to-face lunch meetings (typically at such power spots as Le Bernardin) over cursory phone calls. “A lot of agents can B.S. Over the phone or have notes all prepared, but I could never do that. That’s not how you build up trust with the world’s wealthiest people,” she told Bloomberg.
Here’s what she had to say about her C-suite customers—the good, the bad, and the hyper-demanding.
A Private Jet Is a Business Expense
Private jets for execs and their families are almost always reimbursable corporate expenses. Why? Transportation is considered a matter of security, and most CEOs plan travel in tandem with work trips, taking their family with them to Dubai for a few days before jetting off to the Maldives.
“Safety” is a card more legitimately played by former presidents, says India, who has organized trips to Africa for George W. Bush and his 30 secret service agents. But CEOS are productive on planes—she joked that “if you can be offline for 10 hours, then you aren’t really that important.” (In the era of laptop bans, private planes are a good way to ensure that work gets done.)
Privacy also important. “CEOs like to stay under the radar and want to focus on their family rather than who they are,” India said. Speaking of family time: They often travel with their pets, “just because they can.”
Little else gets expensed. “CEOs can splurge big time on hotels, yachts, and experiences when they’re saving a minimum of $75,000 to transport a family of four,” India observed, noting the rough cost of a private jet.
It Takes a Village
For every VIP itinerary, there are “layers of experts” coordinating the logistics, says India. “They have us, an air department [or a team dedicated to booking air travel], and an executive assistant working in unison to make sure everything is exactly they way they like to travel every step of the way.” But having too many cooks in the kitchen isn’t something she worries about. A CEO’s personal assistants prove extra-valuable: One client drinks only O’Douls and has frequent hankerings for crunchy peanut butter; others might like their entire minibar stocked with a particular beverage (think: Coke Zero).
Preferences for air travel can be among the most important to consider. India says some of her regulars might want a particular make and model for their airport transfer (for vanity), some want to be picked up right next to the aircraft (for speed), and others are particular about having two pilots even on a tiny helicopter (for paranoia).
But not every minute is planned. India says her CEOs “like a mix of organized activities and room for spontaneity” on their itineraries, so they have a structured schedule and time to relax.
Loyalty Isn’t Everything
Don’t brag to your boss about your Platinum Elite Marriott Rewards status: Chances are they won’t be impressed. “They don’t care about rewards that offer them amenities or free breakfasts or upgrades—they’d rather book the room they want from the beginning,” explained India.
So does that mean they don’t care about frequent flier miles, either? Sort of. These programs are less valuable for those who tend to fly private, but when the unavoidable commercial flights rolls along, executives “do care about being recognized.” (Privacy, it seems, is less of a concern if it’s what secures a first-class upgrade.)
Bigger Isn’t Better
“Since the way they live normally at home is quite lavish, they love top accommodations,” said India of her guests. The five key things they’re looking for are good light, outdoor space, seamless technology, high-end furniture, and a super-comfortable bed. Specific views (such as the Eiffel Tower or Spanish Steps) might help, too. Square footage is less important: “A good suite is not just about big for the sake of being big,” India explained.
These criteria have shaped India’s shortlist of the best hotels in the world. “In Rome, for example, everyone assumes they should be staying at the Hassler, but I don’t love it personally. It’s great for lunch, but the rooms are highly overpriced.” Instead she books guests into the just-renovated Hotel Eden, where she’s partial to the Aurora Terrace Suite. In Paris, she turns to the penthouses at the Bristol and Plaza Athénée.
As for the rooms and resorts on CEO bucket lists? They include the Brando, a private island resort in Tahiti that was once owned by Marlon Brando; the Four Seasons Bora Bora, whose three-bedroom overwater bungalows are among the best in Polynesia; the AII Royal Suite at the Four Seasons in Lanai, Hawaii; and the private villas at Castiglion Del Bosco, a Tuscan village-turned-Rosewood resort by the fashion mogul Massimo Ferragamo.
From One VIP to Another
India scrutinizes every aspect of an itinerary, from airline routings to the personalities of tour guides. But ultimately she’s not the one executing the services she books. That’s why she assembles a one-sheet of critical details—such things as dietary preferences (allergies, restrictions), an affinity for San Pellegrino over Perrier, a hatred for Jack Daniels, or an addiction to spin classes—and sends them straight to the hotel’s general manager, not the front desk or guest relations team.
“No matter how much hotels say they care about every guest, they tend to lose this type of information,” she explained. This way, she is getting high-powered requests into equally high-powered hands, ensuring that detailed requests such as in-room yoga mats and blenders (for protein shakes) don’t go overlooked. Of her clients’ hyper-specific demands, India says: “I don’t have time for the crap either, so I totally get it.”
Another strategy: booking yachts, villas, and residences instead of traditional hotels. In these cases, she can control the staff-to-guest ratio herself, guarantee privacy, and custom-pick chefs or butlers whom she knows will strike the right chord.
A Predominantly Grateful Crowd
Here’s a shocker: CEOs can be difficult. One hedge fund owner recently sent India a barrage of round-the-clock texts and emails complaining that the weather was too hot in Italy, despite the fact that his family’s activities were all scheduled in the early morning hours. What’s more, India said the 12-year-old kids were as difficult as the parents, with over-the-top criticisms of a luxury spa experience.
This isn’t common, though. India said that by and large, she works with “really nice people who generally appreciate everything.” What is common? Receiving flowers and thank you notes—or even photo books filled with vacation snaps—from happy clients. “It’s thoughtful stuff, not a Ferrari outside my apartment,” she quipped.
Her most appreciative clients prefer a more personal route, opening their homes and inviting India for dinners. “That’s the best thing,” she said. “I never feel looked down upon; I’m being treated as an expert and part of the family instead, and that’s really special. And the next trip we plan for them is even better as a result of getting to know each other.”
