A world away: Why Lāna’i, Hawaii is the ultimate private island paradise

The ultimate status symbol for the rich and famous, above a superyacht or a platinum credit, has to be owning a private island. Look to Leonardo DiCaprio who owns Blackadore Caye, a 104-acre island off the coast of Belize. There’s Sir Richard Branson’s luxury Caribbean nook, Necker Island, and singer Shakira co-owns Bonds Bay, an island in the Bahamas. 

These invite-only sun-drenched boltholes usually offer optimum privacy and exclusivity for high-profile people, but there is one slight exception to the rule. Billionaire Larry Ellison, chief technology officer of software company Oracle and seventh richest man in the world owns 98% of Lāna’i, the 140sq mi lesser-known Hawaiian island. The 80-year-old tech tycoon purchased it in 2012 for $300m (£200m).

Fondly known as Pineapple Island – a nod to Lāna’i’s booming pineapple farming industry in the 1920s and a time when it provided 75% of all these tropical fruits to the world – it is also home to around 3,300 residents, with the remaining 2% of the island owned by the state of Hawaii and individual homeowners.

Lāna’i is fringed with rocky coves, jutting red-lava cliffs and custard-yellow sandy beaches. Inland a patchwork of unspoilt terrain unfolds as rocky lunar landscapes, fragrant pine forests and scrubby bush. And like any celebrity-owned private island worth its weight in gold, privacy-hungry A-listers fly in on private jets or choppers to enjoy the island’s sheltered off-grid vibe in the North Pacific Ocean.INSPIRED OPULENCE

The likes of Bill and Melinda Gates, singer Usher and comedian and actor Ken Jeong have stayed inland at the Four Seasons Resort Sensei, 1,800ft above sea level and ensconced in dense vegetation, while Jessica Alba, Will Smith and Cindy Crawford have booked rooms at the island’s beach-hugging White Lotus-style Four Seasons Resort Lāna’i – two very different five-star properties from the only major hotel brand permitted on the island.

For both resorts, the island is accessible to visitors via an hour-long ferry trip from Maui to Manele Harbour on Lanai or a 25-minute flight on Lāna’i Air from Honolulu. Your luxury experience starts at Lāna’i Air or Manele harbour when a Four Seasons chauffeur will meet you and whisk you to your chosen accommodation.

The Four Seasons Sensei, a 24-acre utopia, opened in 2019 as a partnership between Ellison and US physician, scientist and author Dr David Agus. It’s an adults-only wellness-led resort that focuses on three main lifestyle pillars: movement, nourishment and rest. There are serene pools to lounge around and an airy yoga shala as well as mind-bendingly hi-tech spa treatments and private one-on-one biomarker sessions.Fashionable fare is available at the resort’s onsite Nobu, situated inside a glass pavilion. The jaw-dropping grounds feature ancient banyan trees, towering birds-of-paradise and dinner plate-sized red hibiscus flowers. A series of modern sculptures pepper the property – work by Jaume Plensa, Fernando Botero and Jeff Koons – with onsen pools camouflaged in a Japanese rock garden. It’s both wildly lush and manicured.

In contrast, across the island, the oceanside Four Seasons Lāna’i resort tumbles into Hulope Bay with a part-public part-private paradise beach flanked by swaying palm trees. At the public end, a scattering of lively locals surf, snorkel and barbecue, playing music on portable speakers. Children swim in man-made rocky tidepools. A short gentle hike upwards reveals Puu Pehe (Sweetheart Rock), a rugged landmark 150ft off the coastline that bestows a beloved romantic legend.

The unassuming Lāna’i city (‘city’ being a loose term) is a 20-minute drive from the beach resort on the road to Sensei and the only lived-in settlement on the island – accounting for 99% of the island’s permanent population of 3,367. Quaint and neat as a pin, it remains largely unchanged since it was founded in the early 1900s as a plantation town. There are no major supermarkets, cinema multiplexes, chain restaurants or shopping malls on Lanai and it’s void of public transport and traffic lights, so the unfettered spirit, beauty and culture shine brighter than elsewhere in Hawaii. The private management company Pulama, which Larry founded, oversees the island’s upkeep.UNSPOLT AUTHENTICITY

A good way to explore the island is on foot – hiking the Koloiki Ridge or Munro trails for example – or on e-bikes. For a faster paced adventure cover some of the 400 miles of four-wheel-drive trails (only 30 miles of the island’s roads are paved) by jeep. The Four Seasons HoloHolo (translated as go riding, sailing) can be booked as an independent jeep hire or a bespoke guided tour taking in history, culture and natural beauty.

Lāna’i’s 800-year-old Waiaopae fishpond, which once fed the island’s population when a more traditional fishing lifestyle thrived, is a worthy stop. Kaunolū Village Site on the south coast is a former fishing village, abandoned in the 1880s and a US National Historic Landmark since 1962. In the island’s northwest, Polihua Beach attracts green turtles with its algae-rich environs. and isn’t far from Shipwreck Beach where a grounded Second World War vessel sits off the coast not far from sugary sand and lounging seals. In the winter humpback whales regularly pass through.Meanwhile the western uplands boast a remarkable natural rock garden: Keahiakawelo (The Fire of Kawelo), nicknamed Garden of the Gods’. It overlooks neighbouring island Molokai and the earth is a rich Mars-like rusty-red colour decorated with bundles of bulky orange-tinged boulders and neat rock towers – the claim is they hold the spirits of ancient warriors.

Historically, Lāna’i has always offered its own spin on Hawaiian culture. In the 1790s Mexican cowboys were brought in to teach locals how to care for cattle and there are Mexican influences on the island’s menus to this day, with juicy seafood tacos and fresh mahi mahi ceviche served with tangy pineapple slaw. To take a deeper dive into the island’s history and culture, head to Lanai Culture and Heritage Centre, a museum that tells the story of Lāna’i’s ancient Hawaiian roots up to the present day with artifacts, photos, documents and exhibits on the people and wildlife who shaped the island.

For years, Lāna’i, Hawaii has held onto its reputation as an agriculture-focused landscape, but really it’s the most authentic best-kept secret of the USA’s 50th state – and remains like nowhere else in the world.

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