ON LANAI, the smallest Hawaiian island, deer outnumber people about 10 to one. You might spot a herd from above as you approach the isle in an 8-seat propeller plane. Or as you drive in from the airport, on one of three paved roads, to the only town, Lanai City, where almost all of the island’s approximately 3,000 residents live. One, Larry Ellison, the billionaire tech mogul, owns 98% of the island, so he has about as much run of the place as the roughly 30,000 deer do.
Since he bought the island in 2012, Mr. Ellison has renovated Lanai’s two Four Seasons hotels, turning the grounds of the upland Sensei Lanai into a sort of manicured cloud forest meets Japanese garden meets sculpture park. Under his direction, the other hotel became an airier, brighter beachside resort. Both properties invite cocooning, but haven’t we cocooned enough this past year? Dwarfed by the other islands, the appeals of Lanai—about 17 miles long and 13 miles wide—are often dismissed in favor of the seemingly more rugged adventures on the Big Island, Maui or Kauai. But Lanai is as wild as you want it to be, with sunny cliffs overlooking coves and bays (prime snorkeling spots), misty Cook pine forests (for horseback rides) and sun-scorched scrubland (where the Pineapple Brothers lead deer-hunting excursions).
On unpaved roads at times violently bumpy, I spent a day off-roading to an ancient native Hawaiian aquaculture operation currently under restoration and to a secluded beach on the eastern side of the island—Maui was so close that I could see the sun reflecting on the windows of the resorts on its western shore. In front of me, a whale breached so startlingly near I could hear the splash as its body re-entered the water.
While most rental companies elsewhere discourage off-roading, on Lanai, it’s permitted in Jeeps (though with caveats—rain can turn roads into sludge that has required many a tourist rescue). It’s the only way to reach Keahiakawelo, a boulder-strewn plain exposing Lanai’s striking rust-red dirt and, to native Hawaiians, one of the island’s most storied places. From there, it’s a steep descent to the northwest corner of the island and Polihua Beach, a 1.5 mile white sand beach where you’re unlikely to see anyone else.
You can hire a guide from the Four Seasons, but I opted to go at my own pace with the unexpectedly engaging Lanai Guide app: I learned, for example, that Palawai Basin, a great flat expanse inhabited by Polynesians 1,000 years ago, had also been the site of a Mormon settlement helmed in 1861 by Walter M. Gibson. He was later excommunicated as a result of his “creative approach” to economics—embezzling the church’s money to buy land—but by the time he died in 1888, he owned the majority of Lanai.