Today, though, there's a real sense of optimism about the place. My first sight of Larry Ellison's little slice of paradise is from the air. After the short flight from Honolulu we swoop down towards Lana'i's sheer volcanic cliffs, cliffs that hide a lush green plateau stretching beyond them. Lana'i was once home to the world's largest pineapple plantation.
They say this is the real Hawaii and you sense this is what Oahu and Maui must have been like before the great tourism boom. Peaceful, sleepy, tropical.
The best way to see Lana'i is by 4WD jeep because many of the roads are just dirt tracks. I take the paved highway to the oasis that is the Four Seasons at Manele Bay. Set in lush tropical gardens, pheasants stroll the lawns to the sound of the surf rolling in on to the golden beach below.
Lana'i is what Oahu and Maui must have been like before the great tourism boom. Photo / Supplied
The Four Seasons is an upmarket property but not at all pretentious. The tone is set by the friendly approachable staff, always ready with a smile and a warm "Aloha!" There's even a Director of Exceptional Experiences on tap to ensure you get the very most from your break.
I snorkel off the beach in the marine reserve, surrounded by schools of bright tropical fish, amazed by the array of live coral just steps from the resort. But it's the spinner dolphins that are the real stars of Manele Bay. They come in huge pods, sometimes hundreds at a time, to frolic in the calm waters of the bay. 'Spinner' because they literally spin out of the water as they leap about.
If golfing's your thing then you'd be hard pressed to better the views from the fairways of the Jack Nicklaus-designed course on the cliffs next to the resort. Or if, like me, you're challenged by small balls, you could just sip a sundowner in the clubhouse.
The rather grandly named Lana'i City is in fact just a tiny village on the plateau set around Dole Square, named for pineapple king James Dole, who was responsible for building much of Lana'i's infrastructure. It was Dole, too, who introduced the plantation-style architecture to the island. It's a time capsule from the 30s.
The buildings are now mostly owned by Larry Ellison and leased by the shopkeepers.
The Challenge at Manele golf course on Lana'i. Photo / Supplied
There's a great selection of eateries here, many of them family businesses and each with their own speciality. Drop into Blue Ginger Cafe and try the chicken teriyaki, or Canoes - its banana pancake with caramelised macadamias takes breakfast to a whole new level! Don't expect a flashy tourist experience here; plastic tablecloths and fluorescent lights abound.
This is the real Hawaii, where the aloha spirit is alive and well. The islanders love the simple life ... I'm with them. They're open, warm, generous and welcoming and while they're cautiously optimistic about Larry Ellison's plans for their Lana'i, they don't want to lose the essence of her charm, her simplicity.
Ellison's company, with the canny name of Pulama Lana'i, or Cherish Lana'i, is setting out to make the island self-sustainable. Ellison has already begun work on a desalination plant so that water is no longer a problem and agriculture can be re-established.
Ellison wants to double the population to six thousand permanent residents. He has already set about winning the hearts and minds of the locals. One of the first things he did was to reopen the town's local swimming pool. It had fallen into disrepair and been closed for years.
Now, it could hold its own in any resort. Ellison has also upgraded the local basketball courts and playground and is in the throes of refurbishing the local theatre. He has enlarged and modernised the general store and has grand plans for an international tennis academy and a university here.
Lana'i has a strong Kiwi connection. In the early days of European settlement the island had a vibrant cattle ranching operation.
Among the ranchers was one George Munro, a conservationist from New Zealand whose name is still spoken with reverence here. It was Munro who planted many of the island's pine trees. He saw the pines as the answer to the island's water shortage after noticing how the pine needles gathered moisture from the clouds and then dripped water into the aquifer. It's thought the pines now provide about half the island's water.
Munro's name lives on in the island's famed Munro Trail, one of Lanai's many stunning hikes.
There's nothing flashy or touristy about shopping or dining on Lana'i. Photo / Creative Commons image by Flickr user Terence Faircloth
Among the island's must-see spots is Shipwreck Beach, home to nesting green sea turtles; the surreal moonscape of the Garden of the Gods, rock formations that really do look as if they've been placed there by mystical power; and a fine collection of ancient Hawaiian rock drawings at both Shipwreck Beach and the Palawai Basin.
Lana'i was a surprise. Its inhabitants, many of them originally from Maui or the southern mainland US, have a genuine affection for their island. Her relaxed, sleepy ambience has a way of drawing you in. I was sad to leave.
Mahalo (thanks) Lana'i.
Larry, I suspect, is on to a winner.
CHECKLIST
Top tip: Don't leave the island without trying the delicious poke (raw fish). It's a Lana'i specialty. You'll find the Lana'i Ohana Poke Market at 834a Gay Street.
Getting there: Hawaiian Airlines flies from Auckland to Honolulu three times a week, with connections to other islands. For getting around, hire a jeep from Dollar Rent A Car in Lana'i City.
Accommodation: Four Seasons Koele (in Lana'i City) is a gracious wooden plantation style building reminiscent of a country lodge. It also has a magnificent golf course.
Hotel Lana'i is an old-style guest house slap in the middle of Lana'i City. Charming and historic. It also boasts one of the finest restaurants on the island - Lana'i City Grille.
Further information: See gohawaii.com.au or DiscoverAmerica.com for more on visiting Hawaii.
