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 br...

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