From pineapples to billionaires: Discovering modern-day Lanai

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From pineapples to billionaires: Discovering modern-day Lanai
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Lanai Island offers plenty of pineapple history, beachy adventures and Larry Ellison-style luxury.

January 9, 2023 at 8:55 a.m.Considering he’s about to spend three weeks in Antarctica, I’m not sure who has more traveler’s envy. But my sojourn to Hawaii’s so-called “Pineapple Island” is undeniably a punch off my bucket list.

Three years before Ellison bought the island, the National Trust for Historic Preservation called tiny Lanai City one of America’s “most endangered historic places.” Now Ellison, who grew up poor on Chicago’s South Side, is building badly needed affordable housing. “Well, it’s Larry’s take on affordable housing,” laughs Carroll. “Every unit has flat-screen TVs and a solar roof from Tesla.”

So is his retconning of the venerable Lodge at Koele, which thanks to Ellison is now the Four Seasons Sensei. Carroll says Ellison kept paying the entire staff throughout the pandemic – enlightened self-interest, perhaps, but still far from Ellison’s less-than-charitable reputation.Ellison owns all three hotels on the island – the Sensei, another Four Seasons overlooking the ocean 20 minutes away, and the boutique Hotel Lanai, which began life as a plantation overseer’s spread.

Still, since we’ve come to the island for our 25th wedding anniversary, I try to make dinner reservations at the ultra-swanky Sensei by Nobu – only to learn it’s exclusively for hotel guests only. Thankfully, a friend who once worked closely with Ellison pulls some strings to get us in for the big night. Call it Silicon Valley networking, island-style.

Meanwhile, the state of Hawaii – which owns the 2 percent of Lanai that Ellison doesn’t – is proposing to develop an agricultural park for small farmers. One county councilman calls it “a chunk of land of our own that Larry Ellison won’t have a say in.”

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