Four individuals wearing blue flight suits walking away from a spacecraft after what appears to be a successful space mission or landing
Out of this world: the super-rich might like to join Jeff Bezos and fly into space on their next holiday © Joe Raedle/Getty Images

Recently, I was talking to a wealthy friend who was outlining his upcoming family holidays to me. What struck me was how every minute was accounted for.

Each day was crammed with activities: balloon rides, white water rafting, foodie extravaganzas and cultural excursions . . . It all seemed a bit contrived and rather hard work.

But, when I thought about it, it made sense. If you’re like my friend, your working days are probably like this — filled with productive activities, almost certainly organised by someone else. So why wouldn’t you expect a jam-packed vacation itinerary?

You’re wealthy enough to outsource the organisation and purchase high-status experiences. And you probably want your holiday to deliver measurable outputs (which you can post on Instagram in order to burnish your brand in the eyes of colleagues and similarly status-conscious friends).

A few years back, Philip Hancock, a professor at Essex Business School, talked to me about “the professionalisation of everyday life” — where people view leisure activities in the same way as work, with goals and performance indicators. It’s a phrase that has stuck with me — and this professional family holiday seemed very much along these lines.

Others take a similar view: in a recent interview with the New York-based website The Cut, Jaclyn Sienna India, who runs a members-only travel agency, said: “Many of [my clients] have had successful business careers that require them to delegate, so it’s easy for them to delegate in their personal life, too. And they treat their personal life like a business.”

But this sort of “productive holiday” isn’t the only kind. Some wealthy people prefer to do very little in luxury. I get this too. You work hard, you want to relax in opulence. Clay Cockrell, who runs Walk and Talk Therapy, a counselling service that focuses on very rich individuals, says: “Many wealthy people are constantly on the go. Not just work, but moving between multiple properties. By the time they go on holiday, they’re mentally exhausted.”

This is doubtless part of the attraction of places such as Richard Branson’s Necker Island, or the fly-in, fly-out holiday centres you find in places like Fiji, where you can spend about $200,000 a week to rent a private island. There are other draws to the hermetically sealed luxury of remote resorts, too.

“Large numbers of rich people are very, very private,” says Cockrell. “Many of them only want to associate with other wealthy people when on holiday.”

The reason for this, he explains, is that it’s easier to be with your tribe. “If you’re with other people in the same wealth bracket, you have the same interests and there’s no guilt about spending. You can all afford to do the same sort of thing.” There are degrees of this: you don’t have to go to private islands — you can also find it in places such as the Hamptons and the south of France.

But some wealthy people don’t want luxury at all. These are those who crave adventure. They might seek an exclusive high-end experience — such as visiting Antarctica or even outer space, as Jeff Bezos does. But often it’s really demanding challenges, like climbing Everest, running ultra-marathons or trekking across Borneo. There’s the physical toughness, and the status that comes with that. Not showering for two weeks and putting up your own tents as you walk across the Atacama Desert or the Mongolian steppe is a challenge — and a novelty.

Cockrell says another interesting trend he’s seeing is holidays with a very defined purpose. “You might visit all the wineries in a part of California or France, or follow a sports team. Many successful businesspeople are hyper-focused — and this sort of holiday appeals to them.”

For ordinary, middle-class “civilians”, the more regular holiday haunts of the wealthy can seem strange places. Many years ago, while I was backpacking with the woman who is now my wife, I met an academic on a flight from Papua New Guinea to Bali.

He did work that was funded by an American philanthropic foundation and was usually in some of the most remote regions on earth. But, when he wasn’t, the foundation tended to put him up in the kind of places where its rich patrons stayed. And so he invited the two of us for dinner in an ultra-luxe resort on an isolated stretch of coast on Bali.

When we arrived, I made suitably complimentary noises about the carefully curated luxury around me. He gave me a pained look. “Sure, it’s great,” he said. “Amazing. Wonderful. But I just want somewhere normal to hang out.”

Rhymer is reading . . . 

The Mountain in the Sea by Ray Nayler, a thriller about alien intelligence (in the form of octopuses) that takes in language, biology, artificial intelligence, corporatism and geopolitics.

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This article is part of FT Wealth, a section providing in-depth coverage of philanthropy, entrepreneurs and family offices, as well as alternative and impact investment

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