Love Lana’i (A Cranky Travelogue)

It’s a Wednesday so that’s not a normal posting day, but I have a not-so-normal post for you. Since I received great feedback from my inaugural Cranky Travelogue about my trip to Islay, I thought I’d do a quick one for my brief visit to the island of Lana’i in Hawai’i.


I have unfairly stereotyped the Hawaiian islands. Not that it helps, but it wasn’t actually all the islands. No, it was just the littlest of the six islands with guest accommodations on them, Lana’i. Having had a wonderful visit to Moloka’i two years ago where I learned about the friendly but fierce attitude of native Hawaiians against growth and outside investment, I figured I might find some of the same on Lana’i. After all, they’re both smaller islands with limited visitor infrastructure, right? Nope. I was wrong. These islands couldn’t be more different.

While Moloka’i is proudly anti-development and many folks there are in favor of Hawaiian independence from the US, Lana’i is different. Much of this stems from the island’s former status as the pineapple capital of the world. By the time Dole was done building its pineapple kingdom, Lana’i had been filled with immigrants to work the more than 16,000 acres of crop. The largest group came from the Philippines, and their descendants have remained. Filipino blood makes up the largest population of all groups on the island.

When Dole pulled out of Lana’i in the 1990s, it was a shock to the system. The island had already been sold a couple of times, by 1985 it went to someone the locals repeatedly referred to simply as Murdock. That’s actually David Murdock, a former Dole boss with a lot of money to spare. He pushed for the move to tourism and built two luxury hotels on the island to complement the one small Hotel Lana’i that had been there for ages.

After Larry Ellison bought the island in 2012 (or at least, the 98 percent of it that was owned by Murdock), there was concern about what he would do. Most people I spoke with were quite pleased with how things have unfolded. He has invested in the community, something that was apparently lacking toward the end of Murdock’s reign. I remained confused why someone like Larry Ellison would want to buy a place like this, but I started to see a picture forming after spending time there. It looks like he’s trying to create a model for the sustainable community of the future. It’s a lofty goal, but it’s one that can only benefit the island’s residents. And if it works, then it’s something he could export elsewhere.

Lana’i City — better known as “town” — is where nearly every one of the 3,500 residents on the island lives. Town is a fascinating place. It sits over 1,500 feet up on the side of the volcano that formed the island. Many years ago they planted pine trees in the area, so it now feels like a pine forest, very different from what you’d expect to find in Hawai’i.

Town is centered on Dole Park, a large grassy square that is surrounded by the town’s commercial center with two markets, restaurants, and even a small movie theater. The Hotel Lana’i sits at one end. Homes radiate out from the center. An old Dole admin building is now a cultural center.

In front of that building is the last tiny little patch of pineapples left growing on the island.

Murdock’s hotel that was built near town is now called the Lodge at Koele. It was more of a hunting lodge — hunting deer and birds is a huge part island life — but it has been closed for several years. It is expected to reopen later this year as a wellness retreat. I hope to return to visit it since it feels nothing like any other resort in Hawai’i. In fact, for years, it was a place where Hawaiians from all islands would visit to get as close to a wintry mainland feeling as you can get.

The other Murdock hotel is where we stayed — now called the Four Seasons Resort Lana’i — and it’s way down on the beach at the south end of the island. You drive from town for about 20 minutes, first through the Palawai, a caldera that was covered with pineapple fields and now sits full of weeds and native plants. Then you descend down the side toward the coast via switchbacks. This side of the island is dry, but you know you’ve arrived when you see the planted lush green lawns that seem out of place.

Disclosure: The Four Seasons provided me with a travel agent rate thanks to Cranky Concierge’s work that averaged to $200 per night for two nights. This can be up to $1000 below the published rate on some nights

The hotel was previously named the Four Seasons Manele Bay, and that’s a really strange thing in itself. It turns out that Manele Bay is the next bay over where the ferry from Maui arrives. The hotel is actually located on Hulopo’e Bay, but when they built the hotel they figured it would be too hard for people to pronounce it. That’s a shame, because Hulupo’e Bay deserves to be recognized. It’s a picture perfect crescent of sand with areas for picnicking and other shenanigans behind. The Four Seasons is perched imposingly up on a hill toward the west side of the beach.

The hotel is spread out between eight different low-slung buildings that hold all the rooms. I got lost more than a couple of times trying to make my way through the maze of outdoor corridors. This doesn’t even include the golf course and villas which sit further away from the core hotel itself.

As you’d expect from a Four Seasons hotel, the service was outstanding. We were greeted with leis and fresh pineapple juice and escorted by Summer to help us get our bearings. She checked us in and then walked us to our room.

The room itself was quite nice with a comfy bed, dark woods, a gigantic television, and most importantly… a fancy Japanese toilet that I’m fairly sure had become sentient. When Skynet goes live, we should all be worried, though my wife was clearly unconcerned.

To me, however, the room was a sideshow. I understand that most people who travel to a Four Seasons on a relatively remote island like this are looking for luxury, pampering, and relaxation. They want someone who will move the umbrella to make sure they don’t get sunburned. And they can get all that at this hotel, but it’s a complete and total waste of a vacation. This hotel gives a very unique opportunity to learn about the culture and even participate in it. This has to be the hardest challenge the hotel faces. How do you find people with enough money to afford the 4 digit nightly price tag who also really want to be immersed in the culture?

The hotel was given a makeover just a few years ago after Ellison took over, but it’s a more recent program called Love Lana’i that has resulted from an effort to focus more on the culture. It sounds like uptake has been far lower than you might hope, and that’s only mildly surprising.

Some of the cultural efforts are easy, but apparently that’s still a hard sell. When we arrived, Jay was hand-sewing fishing nets that will be used to take guests fishing once completed. It’s easy for a guest to stop by for a second and learn a bit about the practice. Then there is the sunset ceremony which kicks off with the blowing of the conch shell, a Hawaiian prayer, and then a hula dance. My wife and I watched it both nights before dinner and had the chance to speak with those practicing their art afterwards. I don’t think there were more than 10 people watching either night.

If it’s hard to get people to participate in that, then imagine how hard it is to get people to join in some of the events that are further afield. There is a sunrise walk to Pu’upehe (sometimes called Sweetheart Rock), the lonely rock formation that lies between Hulopo’e and Manele Bays. I didn’t do that with them, but instead my wife and I did the mini-hike ourselves the first afternoon. Not only is it beautiful but there’s an entertaining Hawaiian legend behind its existence. As an added bonus, the walk from the resort — which goes right by the beach — passes by ruins of an old Hawaiian settlement. There is ancient history literally right outside the door.

It would be a mistake to stay isolated at the resort, however. There is a Holoholo Experience where they will take you out in a Jeep or SUV around the island to show you whatever you’d like to see. Incredibly, they don’t charge extra for this. Remember Jay who made the fishing nets? He took us out and showed us town along with the two biggest attractions for tourists on the island.

Shipwreck Beach lies at the bottom of a dizzying road on the remote north side of Lana’i. In the distance is a prominent view of both Moloka’i and West Maui. But in the more immediate foreground toward the west is a rusted out hulk of a ship that the US military abandoned more than a half century ago.

We climbed back up the mountain and then headed west toward Keahiakawelo which translates roughly to the fire of Kawelo. Legend says that the kahuna Kawelo burned a bonfire here and that’s why it is devoid of any vegetation. You can learn more here. Some refer to it as the Garden of the Gods, a name that stuck because the Mars-like landscape is reminiscent of the place in Colorado with the same name, but that isn’t the preferred name, nor is it accurate.

Visiting these places is one thing, but actually getting a guided tour from a native resident with great knowledge is something else entirely. For example, as we drove along the dirt roads, I saw black flecks everywhere. What was it?

Jay explained that back in the pineapple days, they used to lay down layers and layers of black plastic to help the pineapple grow. That isn’t biodegradable, and it only pops up as the soil erodes, as you readily see on roads. This covers the island, and it’s a big problem. Jay told us that Larry Ellison has a team looking at it. This kind of backstory makes the experience fare more interesting.

And that really brings me to what made me love Lana’i. Yes, you can visit Lana’i and have a relaxing, wonderful time. But if you don’t talk to the locals, you’re really missing out. Jay told us about his family, about his hunting skills, and about life on Lana’i, but he was just one of many people we encountered along the way.

At the resort, I eagerly looked forward to breakfast when Bryan was at the helm. Bryan was a proud chef who seemed to love the ocean view from his “office.” He had plenty of ideas of foods to make for me, so I just asked him to run with it. One day I had an omelette/bulgogi combo that was just outstanding.

While he cooked, he told me about all the exotic fruits that were there including pepino melons, dragonfruit, lychees, horned melons, gold kiwis, and more. He was enthusiastic, to say the least, and that woke me up better than any caffeinated drink.

Then there was Uncle Bruno. I first encountered him while I was walking back to my room past the bird cages that house three of the seven birds that have been rescued by the resort. At the time, Uncle Bruno was enjoying the morning with his friend, Ke’o Ke’o. This was, as you probably guessed, a bird. And that isn’t a surprise since Uncle Bruno is considered to be the resident bird whisperer. While he works with all the birds, Ke’o Ke’o is special.

Ke’o Ke’o sits with Uncle Bruno and chews on his necklace. He undoes his shirt buttons, and he talks… a lot. Uncle Bruno talks to him like a child, rubs his belly, and just seems happy. But Uncle Bruno isn’t the star. While we were there, it appeared there was a shift change. An army of workers rolled by, all saying hello to Ke’o Ke’o as they went by. He is the real star of the show.

I also must mention Ulukoa, a former archaeologist who is a native of O’ahu. He had given up that life and only moved to Lana’i two months earlier as one of the Love Lana’i employees with a cultural focus. Ulukoa grew up learning both hula and ‘ukulele, and any time he’s there, he’s happy to give lessons and “talk story.”

I grabbed my own ‘ukulele and planned to spent a little time taking a lesson with him. It turned into a two hour long hang that ended with him offering to show us around if we were still on O’ahu when he returned.

When we were done, Ulukoa introduced me to Uncle Bulli who was weaving a coconut palm hat. He also teaches the ‘ukulele, though they have different styles. I was simply trying to be polite when I said I liked his hat, but he insisted that I take it. I wore it the rest of the trip (as you can see in other photos here) since I wanted to honor the amount of work he had put into it. (Oh, and I also liked it.)

What’s most interesting about all this is that none of these experiences cost anything extra. They just require a little bit of effort, something that would repay itself in spades in short order.

The one cultural experience we did pay for was the ‘Aina Ahiahi, a Hawaiian tasting menu for dinner. We found out that we were only the second couple to have signed up for the meal experience which was a reasonable $125 per person including tax and tip.

The food was a set menu, but we were able to customize the entertainment. While having musicians or dancers at the table were an option, that would have made me uncomfortable being the focus. Instead, I asked to have a “host” join us for our meal. We were lucky enough to have 19-year old native Isabel join us. We were greeted with hand-made leis (mine from the kalo leaf) and then we sat in the far corner of one of the restaurants.

Isabel loves the island and told us all about life there. She answered most of our questions frankly — I say “most” because she wouldn’t confirm where Larry Ellison stays when we comes to the island for privacy reasons — and it was quite special to have the time with her in such a relaxed setting.

Talking to Isabel was the best way to understand why Lana’i evolved so differently than Moloka’i. It was much more diverse thanks to the pineapple fields. She explained that she learned Ilocano (one of the native languages of the Philippines) before she even learned Hawaiian. There just isn’t that fierce independence streak that you find on Moloka’i.

Dinner itself was uniquely delicious and completely filling. We had poke and poi along with he’e luau made from kalo leaves and squid that tasted like a far superior version of creamed spinach. There was kalua pork and lau lau along with sweet potatoes. It was a true feast despite it technically being just a tasting.

My wife and I talked about why the uptake might be so low, and the next day we walked up to talk to Rachel, another member of the Love Lana’i team, about some of our thoughts. My wife used to do management consulting, so she was full of ideas. I half expected her to whip out a Powerpoint presentation.

Overall, I enjoyed my visit thoroughly. That being said, without the cultural interactions, it would have felt like just another resort but without much “place” to it. The hotel is so far removed from town that it’s like an island of its own. And it takes just a little bit of effort to get beyond that feeling.

That being said, I have to add that I don’t see traditional relaxing at a resort as a bad thing. My wife took full advantage of the spa. (I just spent some quality time in the sauna.) We both snorkeled in Hulupo’e Bay — the hotel provides the gear for people at its beach hut without charge — and had a great time sitting both on the beach and by the pool reading and napping. Having the attendants bring us ice cold water coolers and adjusting our umbrellas was absolutely welcome.

But I can do that at any Four Seasons resort in a warm climate. Taking advantage of what makes Lana’i unique was what made the trek worthwhile.

Before we left, Rachel came by and gave us both baseball caps as a thank you for coming to visit and participating in the cultural events as much as we did. As we boarded the bus, one of the hotel’s employees played Queen Lili’uokalani’s famous song Aloha ‘Oe on his ‘ukulele.

The song ends with, “until we meet again.” I’m hopeful that day comes sooner rather than later.

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16 Responses to Love Lana’i (A Cranky Travelogue)

  1. Gary WI says:

    Thanks for the great summary. I am due to visit next month and you have given me some things to think about. I am guilty of visiting Four Seasons Resorts and doing very little except visiting the pool and beach.

  2. jyarmis says:

    Fabulous writing. You brought the place to life. Maybe you should take requests from us, your readers, on where to go next. (No, not there!) Looking forward to more like this.

  3. Iron Man says:

    Thanks for this lovely travelogue. My parents honeymooned there (then called The Manele Bay Hotel before the Four Seasons began managing it) when it was first built in the early ’90s. We went back a few times as a family and it was always a tremendously special experience as a kid, in large part because of the dedicated staff and natural beauty surrounding the resort. Sounds like many things have stayed the same but there is a much deeper focus on the island’s history and culture than I remember, which is great to see. Maybe I’ll have to become a travel agent so I can afford to return! ;)

    • David M says:

      “then called The Manele Bay Hotel before the Four Seasons began managing it”

      Ahh, the good old days when they were part of Starwood’s Luxury Collection portfolio and you could redeem SPG points for stays there and they offered reasonable Kama’aina rates. My parents took a few trips to The Lodge back then.

  4. David SF eastbay says:

    Sounds like you had a nice relaxing stay.

  5. Whwgrl says:

    What a great trip. I grew up on Oahu and been to outer lslands, but not Lanai.
    Im glad you both had a terrific time, and like you said talking to Locals you Learn alot from them and they have great stories to tell.
    Aloha!!? I

  6. Henry says:

    Outstanding travelogue. I’m very impressed with the extensive variety and apparent quality of the resort’s cultural activities. Maybe after I win the lottery I’ll be able to afford a stay there.

  7. iahphx says:

    Thanks for the travelogue. The Four Seasons sounds like a great hotel — if only mortals could stay for less than $1000/night! I found your report about the other guests ignoring the cultural activities to be interesting. I stayed at the Fairmont Orchid on the Big Island (on loyalty points) a couple years ago and they had a good free cultural program, too (not as good as what you describe at the Four Seasons, though). Although the Orchid is a fairly large hotel, my family was the only one in residence taking advantage of the activities. We found this a little weird, but didn’t mind: we had some great free private tours!

  8. You captured the essence of the island from behind the gilded cage of luxury, and that requires some work, well done!

    For a perspective from a shoestring budget, here’s my vision of Lanai from sleeping on the ground a hundred meters away from your hotel room: https://worldwidewilbur.com/things-to-do-in-lanai/

  9. Yo says:

    Beautiful. Other than a few brief scuba trips and a boat ride to a remote corner of the island for some lame tourist boat I’ve never explored it. My boss (more like my boss’s boss’s boss’s boss) owns over 90% of the island…but we don’t get discounts at the hotels…LOL….

    Maybe next trip, but I still gotta explore Molokai…

    Good stuff Cranky!

  10. Rowdy Yates says:

    Had a great visit years ago. However got “scammed” renting a jeep. They said to leave it at the airport and put the keys in the glovebox. Later got a bill for a non-existent scratch on the fender. Lesson learned.

  11. Al9000 says:

    I edit AAA’s magazine about Hawai’i and am often asked about L?na’i. Now I can refer people to this. Very nice.

    I hope access to the Munro Trail reopens when the Four Seasons in town reopens. That’s a worthy hike.

  12. cos999 says:

    I believe both Bill Gates-1994 and then Mark Zuckerberg-2012 bought out every hotel room on the island for their weddings so as to keep publicity hounds off the island. I first traveled to Lanai in JUly 1990 and there were still lots of pineapples and the snorkeling off of Hulopo Bay was outstanding.

  13. Excellent write-up! And what a fantastic stay. I’m glad you took the time to learn about Hawaiian culture instead of just lying around by the pool. By the way, since you’re spending a significant amount of time on Oahu, I encourage you to check out Mud Hen Water for dinner one day. They do a mash-up of Native Hawaiian and local comfort food with a twist. One of the best and most unique restaurants in the state, in my opinion.

    • CF says:

      Island Miler – Damn! I got home Saturday. I’ll have to put this on the list for the next trip. I see that’s right next to Town – same owners?

      • Yup! Mud Hen Water is by Chef Ed Kenny too. Their He’e Luau is among my favorites, with a more savory note than you’ll find elsewhere. The Yaki (grilled) Pa’i’ai shouldn’t be missed too. Other favorites include the roasted beet poke, the charcoal cooked fish, and the brownie made with keawe bean flour and cooked in the keawe wood-burning hearth.

        Oh, and go to Waiahole Poi Factory out by Kualoa Ranch if you get a chance too. Great Hawaiian food, but their signature item is the Sweet Lady of Waiahole – warm kulolo (taro + coconut + brown sugar) with a topping of haupia (coconut) ice cream.

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