Hawaii’s Lana’i: History, Nature & Hiking


After a few days of luxurious relaxing on Lana’i I was ready to get dirty and really explore the island so I set out to learn more about the history of Lana’i and quickly learned that South Lana’i’s Kaunolu trail is where you can find all of the stories of the past.

Red dirt of Lanai

This trail on South Lana’i is only accessible by 4 wheel drive so I headed out with Steve Gelakoski from Island Adventure Fitness for a hike and a little history.

Steve knows the island so well, it was quite amazing to simply hear his stories and learn more about the landscape, the wildlife, and the conservation/eco projects that were happening in Lana’i. On a side note – one of the things that the new owner of the island, billionaire Larry Ellison, wants to do is make it a sustainability lab — I found most of the locals cautiously optimistic about his ‘green’ plans.

We started at the top of the ridge hiking down the red dirt road ruts until we arrived at some old placards pointing out some historic sites. The signs and sites had honestly not been kept up to well, but you could see the outlines of some of the fishing village stone foundations. The old fishing village has a royal past that Lana’i is quite proud of.

Kanunolu village  - old foundations

Once we arrived at the village the landscape near the sea changed – it was very rocky and we had to scramble up and down some steep rocks in order to get to the sacred heiau. The heiau had a beautiful view of the sea and we stopped and gazed out on all of the fishing boats who seemed to be having a great day fishing  based on the shear number of them working in the channel. The area also was dotted with petroglyphs from ancient times. Some of the first inhabitants of Lana’i lived here. But be warned – this is a sacred place and visitors should not be climbing on these sites or the heiau. I talked to a few locals who actually won’t visit this area of the island since it gives them an ‘uneasy’ feeling.

Steve then led me to Kehekili’s Leap (aka Warrior’s Leap) where cliff diving was supposedly ‘created’ when King Kamehameha’s warriors proved their bravery by leaping aprox. 70 feet into the ocean below. I walked up to the edge gingerly, took a deep breath, and simply peered over the rock to the turbulent ocean below while I had a death grip on the rock next to me.

This cliff seemed to come out of nowhere – which is what made it even more breathtaking. It is said that the water below is only about 15 ft. deep – and one must take a running start in order to clear the rocky coast below. Jumping off this cliff is something I will be happy to NEVER do.

However for those of you who get jazzed by heights and don’t need a barf bag – take a look at the Red Bull Cliff diving competition held in Lana’i in 2000 off of Kahekili’s Leap.

Finally the hard part of the hike came – the walk back up the treeless, barren landscape back to the truck. Steve was great and took lots of opportunities to rest and take in water else my stubbornness would have had me powering through and dehydrated I’m sure. The hike left me exhausted, thirsty and covered in red dirt – but I loved the chance to get out to this remote village and glimpse into the past.


Kaunolu Trail
Difficulty: Medium to Hard (mainly because there are no trees to shade you and the walk back up the hill from the old fishing village is quite exhausting with no shade.
Distance: About 3 miles round trip – but it depends on where you start from on the ridge.
Landscape: Dry, barren, brushy landscape, old ruins, heiaus (old sacred temples), and shocking cliff views

Disclosure: I was a guest of Visit Lana’i as a part of their New Media Artist in Residence Program.  All views expressed here are my own honest opinions and do not reflect the views of my hosts/sponsors.


Sherry Ott
Sherry Ott is a refugee from corporate IT who is now a long term traveler, blogger, and photographer. She’s a co-founder of Briefcasetobackpack.com, a website offering career break travel inspiration and advice.

Additionally, she runs an around the world travel blog writing about her travel and expat adventures at Ottsworld.com.com.
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