The Hawaiian island of Lanai is an unusual place. It’s a playground for the super-rich and yet much of its 364km2 remains undeveloped. Locals are proud that there’s not one single traffic light on the island.

Local artist Mike Carroll told me there are only 3,000 inhabitants. “Once you go fifteen minutes outside of the one town that we have, you may not see another person all day. It’s unlike any other place that I have been,” he told me. “This is truly a special place. It’s very low-key.”

When dotcom billionaire Larry Ellinson bought most of this lesser-known Hawaiian island, it seems that he wanted to preserve Lanai’s charms and just make subtle improvements. You can now buy the fine foods that you’d expect in a New York deli in one of the island’s recently remodelled grocery stores but aside from its two golf courses and two luxury resorts, Lanai is pretty much as nature intended.

The island’s only town, tiny Lanai City, resembles a 1920s movie set. You could re-make The Waltons here. It was built at the cooler elevations in the middle of the island to house workers for the Dole company’s pineapple plantation. Lanai once produced three-quarters of the world’s supply of the canned fruit.Local historian Kepa Maly told me they started constructing the city in 1924 and today, much of what you see is as it was originally laid out by James Dole. There’s been little development to spoil the historic appearance because the capital has been, effectively, a company town. Kepa explained, “Since Western style land ownership evolved in the Hawaiian Kingdom in 1848, Lanai has been largely controlled by one individual. In 1906 it switched from lease to ownership and has been a one-company town, either ranching, pineapple plantation or more recently as an exclusive resort area.”

The town’s wooden chalets are on streets that run towards a massive village green lined with huge Cook Island pine trees, planted to extract the moisture out of the often foggy air. Each can take in 200 gallons of water per day.

The main road out of town is lined with the trees, which adds interest to the otherwise featureless, volcanic scrubland in the interior. I met with Kepa at the Lanai Culture and Heritage Center, which is filled with island artefacts and old pictures. It’s effectively a museum. The team has developed an app offering information on the history of over a hundred locations, including historic buildings and some of the sacred sites. It’s worth visiting.

If you’re interested in local art, there’s a community art centre just off the village green. Inside, the work of twenty island artists is displayed. The centre covers a whole range of arts and crafts from candles and ceramics to photography. “Not bad for a population of 3000,” joked Charles, who was on duty when I called in.

A few doors down you’ll find Mark Carroll’s gallery. Mark visited in 1999 and fell in love with Lanai. He and his wife moved from Chicago and he traded work as a commercial and medical illustrator to capturing the island’s beauty in oil paints. “It’s hard to find a bad spot to paint on this island,” laughed Mike. “Whenever I go for my morning walks I see places to paint everywhere. That’s another surprise here. We’re small but we’ve got these great vistas.” You can see Mike’s work at

Mike Carroll

Lanai is a small community and I loved its unique take on the What Happens In Vegas Stays In Vegas slogan, which I saw printed on a souvenir shirt. It read What Happens On Lanai Everybody Knows. Lanai might appear to be from a different era, but as I said before, the island’s facilities are up-to-date and meet the standards of its demanding guests.

Mike told me that the theatre here was shuttered for about our five years until Ellison’s company restored its 1930s façade. He described the venue as, “the best in the state.” Mike said the community pool had also been closed for about five years, but has now been turned into a pool that rivals most resorts – and it’s free.

After a pleasant morning in the cool, shaded town it was time to explore the historic sites. Kepa had assured me that there was a lot to uncover. “We have a history that spans nearly 1,000 years of Hawaiian residency. The original Hawaiians travelled over 2,000 miles across the open ocean in canoes to settle here,” he told me. Exploring Lanai is still an adventure. There are few signs and not all the roads are surfaced so you have to hunt down its historic sites on dirt trails.

You will need to hire a 4×4. I arranged one, and narrowly escaped being arrested because of it! I arranged to hire a car from the hotel receptionist. On this trusting island I was told that the vehicle would be dropped off at 9am the next day and the keys would be left inside. There was no paperwork. There were only two people staying in my hotel so when the car arrived at 9.25am, I leapt in and went off exploring. On my return I was severely reprimanded. My car rental man had been delayed dropping off my rental. I’d taken the wrong vehicle – one that had been returned for collection by a different agency. Thankfully it wasn’t needed. I was informed that I was lucky that they didn’t call the cops about the ‘stolen’ vehicle!

During my drive, I headed to Sweetheart Rock, a 7-mile drive from Lanai City. Mike Carroll had ‘sold’ it to me. “It’s a sea stack that’s located not too far from the Four Seasons resort,” said Mike. “It’s beautiful during the day and at sunrise or sunset it glows orange. It’s a magical spot.”

You can take a short walk from the Four Seasons resort around the headland to view this 80-foot high chunk of red-coloured stone, separated from the main island by 150 feet of churning ocean. Legend says that a local warrior captured a beautiful princess from a neighbouring island. He kept her in a sea cave because he didn’t want other men to fall in love with her. Whilst he was away there was a storm and she drowned. He was so upset he committed suicide by jumping off the rock.

My next stop required a very bumpy 40-minute run out from Lanai City. It’s a tough off-road drive, dodging the massive boulders that litter the track. The Garden of the Gods is a landscape dominated by red rocks and lava formations. There’s nothing apart from grasses and shrubs and your car will be covered in red dust after driving through it. And locals have another legend to describe how it came to be. According to folklore, two priests were in competition to keep a fire burning for the longest time. The Lanai priest used all of the vegetation to stoke his fire and that’s why the landscape remains barren. It is an incredible, unworldly sight.

If you are driving around Lanai it’s worth looking up the coordinates of your destination on Google Maps and putting those numbers into your satnav. There are few road signs and even with a TomTom, I had to guess which turn to take at quite a few junctions.

I drove for 30 minutes to the island’s most important site, a former residence of Hawaiian royalty on the southern tip. I knew I had arrived simply because the dust road ended. Mike told me that the Hawaiian king came for seventeen summers in a row from the late 1700s. He considered this spot, Kaunolu, to be the best for fishing in all of Hawaii.

There were no mammals on Hawaii so the protein mostly came from the sea and settlers stayed close to the coast. “The cultural and heritage centre here has done a magnificent job,” said Mike. “They are doing a interpretive trail and you can see their altars and the foundations of old thatched huts going up a ravine.” You can still make out the basic shape of what would have been buildings, with piles of rocks at the base where walls once were. You can also hunt for the petroglyphs – ancient rock carvings.

You feel the pounding force of the ocean currents colliding at this spot, as you stand on the mass of rounded volcanic boulders that line the beach. I stared up at the high cliff tops towards the spot where the warriors would prove their bravery to the king. They would jump off this 80ft high cliff into the ocean below, trying their best to clear the dangerous protruding ledge at the bottom. Hawaiians believed that the soul left this world and moved onto the next by jumping into the sea. That makes this site more significant.

If you walk away from this sacred site, you’ll find three corrugated tin fishing shacks that were erected in the 1960s. Mike told me that the three families who look after these are a good example of the spirit of Lanai. “They have signs stating when the family will be back, such as July 4th, Thanksgiving or Christmas. Other than that you can use them.” I asked what they’d do if they came down and there was somebody in their shack. “They’d say, ‘we’ll share.’ It’s an easy going island,” smiled Mike.

I switched from driving on the bumpy road, dodging boulders, to driving on sand to reach the third site I’d been told to see. In the northeast corner of the island you’ll find an 8-mile expanse of beach. There was hardly a soul on the sand – just a handful of picnickers braving the wind and enjoying the great view over to the island of Maui.

An eerie sight frames the view toward the left side of the bay – the rusting hulk of the Liberty. “The actual shipwreck has been there since World War II and it is still sitting there,” Mike told me. “It hasn’t been salvaged. You can drive to it although you will need a four-wheel drive.”

One of the most unusual attractions on the island is the cat sanctuary, which houses over 500 of the animals. The project helps the cats and also protects the island’s endangered wildlife and birds including a colony of Hawaiian petrels, discovered in 2006. The sanctuary has been rated the number 1 activity on Tripadvisor. Co-founder Kathy Carroll, Mike’s wife, met me and unlocked the door fashioned into the high chicken-wire fencing. We toured the huge compound made up of different wooden accommodation blocks and spacious outdoor runs.

Kathy Carrol

“I started thinking of the natural wildlife parks in Africa, which are fenced in but the animals are free within it,” Kathy explained. “The cats thrive in the beautiful year-round weather so why not make a huge enclosure?” The cats have plenty of space – over 15,000 ft². You’ll see them running around, hiding in bushes or trees.

I was keen to find out why so many visitors came. “You can come and cuddle the cats,” Kathy told me. “We call them ‘Pet and Purr’ sessions. We have a partnership with the Four Seasons Hotel, where people can come out and help us feed the animals or even roll up their sleeves and weed or paint. The number one job is sitting with the cats and socialising with them. We call them VIPs – very important petters!”

Kathy told me that a Japanese visitor turned up having walked the mile from the airport and spent five hours volunteering. The tourist revealed that he had travelled from Japan just for this. “He came all the way to Lanai and spent five hours with the cats and then went back. He’s been to 100 countries and has been in similar facilities all over the world, but liked the one in Lanai the best. That really excited us,” said Kathy.

I was introduced to Basil, the oldest resident. He gets extra TLC in what’s termed the Sunset Pavilion for feline pensioners. It’s a cat lovers’ paradise and the passion Kathy and her team have for the job is palpable.

There’s not much wildlife on Lanai but there’s a slim chance you might spot one of the island’s unusual looking wild sheep, the mouflon breed, which sport a distinctive reddish-brown coat.

I had been driving around Lanai’s rocky roads but there’s a more sedate way to take in the scenery – on a cycle ride where you won’t need to pound the pedals too hard! Jeremiah Littlepage of offers downhill cycling tours. “I will drive you to around 2,000 feet above sea level and then it’s a 7-mile downhill ride with wonderful views over the island of Molokai,” Jeremiah explained. “It’s a great way to see the island whether you’re fit or not. All I ask is that riders have some experience and that they know how to brake,” he laughed. “You’ll see Shipwreck Beach from the road, talk about the history and culture of the island, then at the bottom we’ll load up the bike and drive back up to look over the city.”

Jeremy says that you’ll appreciate the island better when you discover it by bike. “The east and west sides of the island are so vastly different. It’s cool to see the contrast. The east side is sloping hills down to beaches. You can see over Molokai and Maui as you come down. The west side is not protected by other islands and have huge cliff. It’s night and day from one side to the other.”

I headed to Manele Bay, where the Maui Ferry docks. It’s a marine preserve and snorkelling amongst the colourful fish in 21°C water is very popular. The neighbouring sands – Hulopo’e Beach – are where locals catch the waves.

I chatted to 19-year-old Travis. He told me that he gets up early to get a session in each day before school. “This is the best beach for surf,” he said. “It’s the easiest access and most of the other surfing spots are only for locals,” he warned. I asked him what makes a good surfer? “If you come off your board get on again,” Travis replied. “Watch the waves and never turn your back on them.”

If that activity has worked up a hunger, head back to town to the Blue Ginger Café and eat loco moco like a Lanai local. It is rice with hamburger patties, gravy and a fried egg. Lanai isn’t a low-carb place! Most menus offer two starches and a protein. Lanai also has its own fruit juice drink called pog, which stands for passionfruit, orange and guava. It’s really good.

If you’re heading to Hawaii for the glamour of Honolulu, I think it’s worth spending some time on Lanai and seeing how varied this chain of islands can be. To reach Lanai, first fly to Honolulu. From London it’s around 18 to 20 hours and you’ll need to change flights at Vancouver, Seattle, San Francisco or LA. You can fly to Lanai from Honolulu or take the 90-minute ferry ride across the 17 miles of sea from Maui.

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