Sometimes, as destinations become very popular, they change. Change can be good – for example, more amenities or nicer experiences – and sometimes they can damage the very thing everyone was excited about in the first place.
In the case of America’s 50th state, Hawaii, the “new” Hawaii is so popular we often forget to stop and think about the old Hawaii. These islands were a remote Polynesian land, later to be ruled by Kings, only to become part of the United States just 53 years ago, in 1959.


This is what most of Lanai looks like - red dirt. Scenic and empty.

Lanai is pretty much the closest thing you’ll get to vacationing on your own private island in the USA (along with Eagle Island, Georgia). On my recent trip to the island of Lana’i (Lanai), my first excursion to these sunny islands, I wanted to look for the “old Hawaii” – not necessarily a place, but an experience I heard could still be had on the island. I honestly wasn’t exactly sure what I was looking for, but here’s what I found.

The History of Lanai

Kamehameha I, the king who united the Hawaiian islands into a single unit back in the early 1800s, made a rather successful attempt at killing everyone and everything in sight on Lanai. (It was the fashionable thing to do back then.) Apart from a several decades of ranching, the island remained rather unassuming until 1922, when James Dole bought most of the island and transformed it into the world’s largest pineapple plantation. Hawaiians from other islands would come to pick pineapples, and everyone on the island was pretty much involved in pineapples in some way – they say at its height Lanai provided 75% of the world’s pineapple. And although Lanai is still called the “Pineapple Isle,” the Dole plantation is long gone, the island still in private hands.

old ferry boat
This is an old ferry boat. The town that was here was abandoned, the ship left to rot and sink right back into the ground.

On your arrival into Lanai, you may wonder if Kamehameha took a second swing, as all the pineapples trees have vanished, and only about 2,000 residents and a couple hundred tourists remain. Apart from the hotel shuttle bus and occasional tourist in a rental Jeep, things are very still, save the occasional wasp looking its next meal.

But as the sun sets, deer cover the lawns in Lanai City, frogs scatter in every direction around the Four Seasons at Manele Bay, their shadows dancing around the torches lighting the sidewalks. Bunnies, visible only due to the moonlight and stars gazing down, dart into the darkness Lodge at Koele. It almost feels like a Stanley Kubrick stage set.


While the pineapples are gone, a trace of their legacy remains: the black plastic that helped keep moisture in the ground. Awful for the environment, I’m sure, but that plastic seems to be all that is holding Lanai’s gorgeous-yet-bumpy red dirt roads together. If you’re in Lanai on a Wednesday you’ll see another reminder of how remote the island is: a container ship floating in the distance, which is carrying the island’s weekly supply of food, household items, and the occasional larger purchase, such as a car.

“Modern Lanai”

During the course of our trip, one of my former consulting clients sent me an email, which I smiled while reading:

I see you are on Lanai. I was there about 17 years ago, way before the 2 resorts. Stayed at the Hotel Lanai. I think they had 5 rooms for $55/night. My wife and I snorkeled at Manele Bay. We and a family of locals were the only ones there. Played golf for free at a Dole Pineapple Company employee’s course. I was only one on the course. One of our most memorable Hawaii trips.

(Hotel Lanai’s prices have gone up a bit, and they’ve doubled in size – now a whopping 11 rooms.)


Getting lei'd at the Lodge at Koele

I wonder if my client would be surprised to see that 17 years later, not a lot has changed. Although the Four Seasons is now operating two properties on the island – the Lodge at Koele and the beachy resort at Manele Bay, a sense of still serenity remains.

For example, the drive up Munroe Trail to the highest point on the island, Lanai Hale, a ride shrouded in clouds and wet, muddy roads. The air smells damp and the trees twist and curl in the wind. I started to wonder if the “man-eating spirits” that were said to live on Lanai in ancient times were still around. Then the clouds parted, and we were treated to a view of three other Hawaiian islands, a view they say you can only get from Lanai.

At Shipwreck Beach, which enjoys fabulous views of Molokai and Maui, a glimpse of an ominous tanker left to rot after WWII left me wondering if the ghosts of soldiers were nearby.


Making the Most of Your Lanai Trip

While part of the charm of Lanai is relaxing – I appreciate you’ve come along way! – I do encourage you to do a bit of exploring beyond the edge of the pool or the terrace of your hotel room. As I mentioned, Lanai affords you the luxury of a private island experience with lots of value-orientated amenities, but there’s more to it than that.

If you do nothing else, please try the free ho’okipa cultural programs at the Four Seasons – make a lei, play the ukulele, dance the hula. It sounds cheesy but it really is a wonderful opportunity. Ask if “Aunty Irene” is teaching – she’s a gem.
Head into Lanai City and go to the grocery store. Welcome to Hawaii, 1950. Not exaggerating.
Take a scenic drive or go on a hike. No matter where you are staying, there are options near by. Get off the compound – I guarantee you’ll notice the air is different, more still, something… undefinable… if you go just a quarter mile from the hotel.
It’s easy to add up the numbers on the “modern” Lanai: 3 main hotels, 2 grocery stores, 1 fuel station, 1 car rental, 1 small airport, 1 coffee shop, 0 stoplights.

Is Lanai a relaxing, luxurious vacation destination? Oh, Yes.

But there’s something je ne sais quoi about the old Hawaiian spirit on Lanai. I can’t put my finger on it, but it’s there. You can feel it.