Luxury resort quarantines — Gen Z's 'old money' aesthetic — Infinity-pool shortage

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Insider Life

Hello, readers! We're back in your inbox this week with a jam-packed edition of Insider Life, bringing you all the best stories spanning real estate, travel, and more. Today, we're giving you a ton of options for your weekend reads — from wealthy people quarantining in the Caribbean to a man who spends his days coordinating jet travel for the rich and famous.

Let's dive in.

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bahamas caribbean paddle board

The wealthy have figured out a way to bypass the United States' travel ban: by quarantining at luxury resorts in the Caribbean and Mexico. The rule bars people from entering the US if they've spent the previous two weeks in certain areas, including the UK and the EU — so some travellers are paying exorbitant prices to bide their time in resorts until they can enter the US.

How staying in a luxury hotel becomes a legal loophole.

blair gossip girl

Gen Z and millennials are bringing back an "old money" aesthetic — think country clubs, dinner parties, polo, and yachts. It rejects the "new money" of the 2010s, on display both by Instagram influencers and hoodie-wearing wealthy millennials, and embraces a preppy vibe that hints at an aristocratic, upper-crust lifestyle. 

Why prep is back and bigger than ever.

San Francisco

Kyle, a 34-year-old tech worker in the Bay Area, still felt broke despite earning $175,000 annually. He was high-earning and not rich yet — until he began socking away an extra $70,000 a year after moving to Phoenix to work remotely. 

He explains how the move changed his lifestyle.

headshot of Marina Shiferman standing in front of staircase

Marina Shiferman, a San Francisco realtor and real-estate coach who makes $500,000 a year,  told us that starting her workdays on Sundays and having slow mornings are key to her schedule. On Wednesdays she has "CEO days," where she focuses on the big picture — business planning and creating ideas.

Here's what a week looks like for her.

hiker wearing a gas mask against a polluted orange Colorado mountain range, with the text

People are flocking to Colorado for its mild winters, wide-open spaces, and access to the outdoors — but air pollution is threatening the outdoorsy way of life that's drawing people in. For the past three months, three out of four days in Colorado have seen air-quality alerts, and it's starting to impact how people spend their days in the state. 

More on Colorado's battle with poor air quality.

Andy Christie headshot in front of a private plane

As the group private jets director for the largest private-charter brokerage in the world, Andy Christie deals with a fair share of extravagant demands from rock stars and the ultra-wealthy. From a woman who spent $40,000 to fly across the country to get a haircut, to a man who diverted his plane to get KFC, he shared a glimpse into a day in his life. 

What it's like coordinating travel for the wealthy.

An infinity pool photographed at sunset.

There's a luxury pool shortage. Materials like gravel are in short supply, and contractors are costly and hard to find, forcing pool builders to set minimum prices as high as $500,000 and turn away customers who are desperate for a backyard pool. We spoke to seven luxury pool designers, who described the unprecedented demand.

Here's what they told us.


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