A place in the sun: Jaclyn Sienna India of Sienna Charles says her clients are often looking for a vibe rather than a destination, but there are requests for private island holidays. Picture: SUPPLIED
A place in the sun: Jaclyn Sienna India of Sienna Charles says her clients are often looking for a vibe rather than a destination, but there are requests for private island holidays. Picture: SUPPLIED

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, no CEO is ever going to spill the beans on his favourite private island, the extent of his security detail, or the lengths his assistant went to procure Coke Zero in Madagascar. But Jaclyn Sienna India, president and founder of travel consultancy Sienna Charles, knows all the details.

She is a go-to for the finance world’s jet set, regularly organising trips for at least two dozen CEOs, other titans of industry and a handful of former presidents. Of the hundreds of trips she plans each year, 90% 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 says, 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 lunch meetings over cursory phone calls.

"A lot of agents can BS 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 says.

Private jets for executives and their families are almost always reimbursable corporate expenses. Transport is considered a matter of security and most CEOs plan travel in tandem with work trips, taking their families 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 organised trips to Africa for George W Bush and his 30 secret service agents.

But CEOS are productive on aircraft — she jokes that "if you can be offline for 10 hours, then you aren’t really that important". In the era of laptop bans, private jets are a good way to ensure that work gets done.

Privacy is also important.

"CEOs like to stay under the radar and want to focus on their family rather than who they are. They often travel with their pets, just because they can. 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 says, noting the rough cost of a private jet.

For every VIP itinerary, there are "layers of experts" co-ordinating 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 the way they like to travel every step of the way."

CEOs’ personal assistants prove valuable: one client drinks only O’Douls — a nonalcohol beer — and has frequent hankerings for crunchy peanut butter, while others might like their entire minibar stocked with a particular drink.

Since the way they live normally at home is quite lavish, they love top accommodations
Jaclyn Sienna Ind

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 organised activities and room for spontaneity" on their itineraries, so they have a structured schedule and time to relax. 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, she says.

Frequent-flier programmes are less valuable for those who tend to fly privately, but when the unavoidable commercial flight rolls along, executives "do care about being recognised".

Privacy, it seems, is less of a concern if it’s what secures a first-class upgrade.

"Since the way they live normally at home is quite lavish, they love top accommodations," says India of her guests.

The five key things they’re looking for are good light, outdoor space, seamless technology, high-end furniture and a supercomfortable bed.

Particular 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 says.

These criteria have shaped India’s short list 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.

Resorts on CEO bucket lists include the Brando, a private island resort in Tahiti that was once owned by Marlon Brando; the Four Seasons Bora Bora, the three-bedroom overwater bungalows of which 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.

India scrutinises every aspect of an itinerary, from airline routings to the personalities of tour guides. She assembles a 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 to the hotel’s GM, 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," India says.

She gets high-powered requests into equally high-powered hands, ensuring that details such as in-room yoga mats and blenders (for protein shakes) don’t go overlooked.

Of her clients’ hyperspecific demands, India says: "I don’t have time for the c**p 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.

CEOs can be difficult. One hedge fund owner recently sent India a barrage of round-the-clock texts and e-mails, 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. India says the 12-year-old children were as difficult as the parents, with over-the-top criticisms of a luxury spa experience.

This isn’t common, though. By and large, India works with "really nice people who generally appreciate everything". She receives flowers and thank you notes — even photo books filled with vacation snaps — from happy clients.

"It’s thoughtful stuff, not a Ferrari outside my apartment," she quips.

Bloomberg

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