Lana'i Holo Holo

Disclaimer: Some of the photos and video in this blog show Trilogy Employees Freediving or exploring the depths on a single breath. This is an advanced skill and we do not recommend trying it solo or without a trained expert.


1. vi. To go for a walk, ride, or sail; to go out for pleasure, stroll, promenade. 

ulukau Hawaiian Electronic Library 

At 5:45 AM sharp, an air of excitement pushed my friend and me around the corner of the Pioneer Inn to behold, Trilogy Elua fresh off drydock, looking as elegant as ever all dressed in white. We were not the last ones to board. Pfew. As we got on the boat and shook off the hurried events of the morning, the relaxing daybreak light settled in on the water and set the tone for the day: we were about to circumnavigate the Hawaiian Island of Lanaʻi.

Approximately nine nautical miles due west of Maui, Lana'i is a privately owned island with 98% of the land owned by former Oracle VP Larry Ellison. The island receives less rain that its neighboring islands of Maui and Moloka'i and though Lana'i may appear desolate on the outside, it is rich in history. When Captain Riley Coon, Trilogyʻs Director of Operations boarded Trilogy Elua with his Father, one of the original founders of Trilogy, Captain Jim Coon, I knew we were in for some real history lessons. Jim carried a weathered wooden box with a handle and latch that I would later learn contained his sextant.

A huge mahalo goes out to Captain Aaron who initiated this company holo holo by offering to lead the circumnavigation around the island of Lanaʻi as a treat and learning experience for the Trilogy staff. With great enthusiasm, several crew members, two office staff, and couple +1's boarded the 55' custom sloop, rigged sailing catamaran which would serve as our own private charter boat for the next eight hours. The motor and sail from Lahaina to Lanaʻi was gentle and gave everyone a chance to meet, catch up and settle in for the day.


Captain Aaron at the helm, photo courtesy of Captain Riley Coon


The first sight of interest was the iconic Shipwreck located off the Northern coast of Lanaʻi. After the second World War, the Navy attempted to sink this ship in the Kalohi Channel. The ship had other plans and came to rest on the reef. Before landing on its final resting spot, the ship, made of concrete, took out a large swath of the reef in its path causing the current U shape. Captain Aaron took great care to navigate the U shaped reef so we had a chance to see the shipwreck without risking damage to our livelihood for the day. Due to the trade winds, this area generally consists of murky waters where sharks are likely to gather so we did not stop to snorkel. The enormity of the deteriorated wreck, perched upon the reef, mostly out of the water created a very uncommon and curious sight.


Photo courtesy of Captain Riley Coon

Video courtesy of Kate Middleton

Polihua Beach

The next stop was Polihua Beach on the North West coast of Lanaʻi. If visiting a beach with seemingly endless amounts of white sand and virtually no one else in sight is your dream, you need to visit Polohua Beach. The current here is too strong for snorkeling, but the view from Elua provoked daydreams of future visits for camping and exploring.

Shortly after Polihua, we passed yet another shipwreck and Aaron noted a piece of this ship has fallen off and into the water within the last several years. "This is like a boat graveyard," I thought to myself. Soon thereafter Captain Aaron mentioned there used to be hundreds of boats wrecked off this side of Lanaʻi, confirming my sentiment.


Photo courtesy of Kate Middleton

Lae o Kaʻena (The Point of Ka‘ena)

Ka‘ena is the point whose name means "the wrath."  The point gets its name from the manner in which the waves crash on the shoreline and create angry frothing water. Aaron called this location "prison" due to its historical use as a penal colony for women. Women who were convicted of a crime under Western law were driven by boat several feet offshore from the point where they were subsequently dropped to swim to shore and fend for themselves. Men convicted of crimes during this time were sent to Kahoʻolawe. The prison was our first snorkel stop. While prison may not sound like a fun place to survey and snorkel, the area underwater was a sea explorer’s playground. Varieties of coral including hues of pale pink-purple, yellow and blue glistened in the water. In a very short amount of time after getting into the water, it was easy to see I was surrounded by seasoned watermen and women, lingering on the ocean floor with only one breath as fuel to inspect and observe the new environment. "Prison" featured several arches formed underwater where one could test his or her skills and swim through. I watched one crew member particularly skilled at freediving head into an arch with no end in sight. A batch of fish came darting out a few feet away, indicating the opening where Siera swam out shortly thereafter. Hanging out below the surface watching everyone enjoy the reef allowed me to see this was surely a group that appreciated the new surroundings.

Video courtesy of Jamie Kleinhenz


Luke Sundquist of Hawaii Wildlife Fund holding fishing line. Photo courtesy of Captain Riley Coon

Back on board, my friend followed bearing a batch of fishing line he and others had loosened from the reef. Trilogy is committed to taking care of the areas we visit and removing marine debris during our tour was one way to contribute; preventing he potential entanglement of precious marine life.

 Honopu Bay

Next stop was Aaron's favorite place to snorkel, Honopu Bay. Honopu or "Three Stone" is unmistakable because of the tall and slender rock formations, that according to legend were once a married couple who angered the gods. Aside from the blowhole and a very cool puka in one structure, the "pool" and cave are what really make this stop otherworldly. Coral walls come up and form a sort of swim lane. As I approached and entered one end, I put my face in the water and jumped. The pool was teeming with so many fish, they were directly in front of my eyes. The long slender fish formed a highway across the surface and the most vibrant parrot fish cruised below me. As I swam further into the pool, it became narrower and fed through to a circular end of the swim lane. Waves were surging and splashing over the edges causing bubbles that made visibility low. A group of five of us were in this little circle for one reason: about 20 feet below was a large arch that formed a 45' swim through. Before we got into the water, Aaron briefed us on all the particular features of this snorkel spot including the massive swim through. Captain Jim advised us we were welcome to venture into that swim through when we came out on our own boat, but not on his watch. Knowing this and my limited experience, I turned around to give the others some space. Back out of the pool, I swam around to the left which followed along one of the tall rocks and into a more calm, shallow area. For a bit, I observed one of my favorites, a little spotted box fish. Back on board, we reported the various marine life we had observed. Chris found a white tip reef shark to the left and Luke from Hawaiian Wildlife Fund saw a green Hawaiian sea turtle.  We learned that Jim's son Riley was, of course, one of the first to swim through the forbidden cave and the footage is epic. Honopu is by far one of the more spectacular locations I have ever visited.

Photo courtesy of Captain Riley Coon

Photo courtesy of Captain Riley Coon

Notice puka on left side of rock. Photo courtesy of Kate Middleton

The swim through. Video courtesy of Todd Warren

The Bubble Cave

Kaumalapau Harbor is Lanaʻi is the commercial shipping harbor for the island. One would not think a harbor that handles shipping containers would be all that interesting for snorkeling, but it was quite remarkable. This harbor was FILLED with an abundance of coral. This is something all of us truly appreciated witnessing since our reefs have been suffering from various pollutants and bleaching events. The beautiful coral was an added bonus, but we had stopped in the harbor to see the bubble cave.  So what is it? It's basically a little cave formation in the side of the rock with a bubble of air inside. Though I am a timid diver at best, it was quite possibly a once-in-a-lifetime experience and I had to at least check it out. "Two at a time" Captain Riley advised us. "Keep in mind when the water surges, it causes a lot of pressure on your ears." Chris was the first to venture into the bubble cave.  He came out filled with excitement and exclaimed that it was the coolest thing he had ever seen, amping up the energy and anticipation for the rest of us. He said the pressure was indeed intense, but totally worth the experience. In an effort to scope out the scene, I dove down and watched two people swim into the cave. They disappeared into the darkness. After a few minutes, the first two did not come out and two more people decided to go in. Into the darkness, they went. People kept going in but no one was coming out. Weighing out all the factors in my mind, the combination of my newness, adjusting to the pressure on my ears, latent fear of water and a dark confined space led me to the decision to leave this one be for the day. Photos from the others are pretty unique.

Photos and video courtesy of Todd Warren


Captain Jim Coon opened up the banged up old case to reveal his sextant. Most people these days have no idea what a sextant is, and to hear its legacy from an old salt like Captain Jim was a real treat. A sextant is a reflecting tool resembling a protractor with mirrors that is used by sailors to determine location using time of day, an astronomical object (in our case the sun) and the horizon. When in the middle of the ocean with nothing but ocean and the sun in sight, the sextant can give a sailor an accurate enough “sight” that when compared with nautical charts, the Captain can determine a latitude and assuredly head in the correct direction. We learned that “Lahaina Noon” is the locally coined name for the sub solar point in time when the sun is directly overhead and a person can stand in their own shadow or a telephone pole will seemingly have no shadow. Hawaii is the only state in the US to lie within the sub solar area. Other states recognize the closest instance of the sun directly overhead as the Summer Solstice. With all of the GPS tools out in the world today, the sextant is losing its recognition. We are happy to learn and keep its legacy going. If for some reason GPS systems are shut down or fail, you know who to call!

Photo courtesy of Captain Riley Coon

Kaunolu Village aka Shark Fin

Kaunolu was King Kamehameha's preferred summer fishing location.  It is said that King Kamehameha would challenge warriors to show their valor by jumping from the infamous Kahekili's Leap. Some aural history of Lanaʻi states those accused of crimes could redeem their name by leaping from the 60' cliff and clearing the rock ledge that sits below. If innocent, they would survive, if not, they met their demise. Since living on Maui, Kaunolu has been my favorite snorkeling location. Because access requires either a boat or 4 wheel drive and a hike I am quite lucky to have previously visited the site twice, and this was my third tour. Also known as "Shark Fin" the area is aptly named for the rock formation in the bay that resembles the dorsal fin of a shark. The depth and visibility here make it a prime free dive site and several spear fishermen visit the area in hot pursuit of tako and local tropical fish. The last time I visited Shark Fin, I was accompanied by an Eagle ray who cruised around the ocean floor for some time. None such luck this visit, however, I had an opportunity to test my newly acquired freediving abilities.  There's yet another swim through to one side of the fin that the group frequented. To the side of Kaunolu is Kāne‘āpua, a recognizable rock formation that has nearly separated from the island. It is named for one of the ancient gods of navigation. 

Photo courtesy of Captain Riley Coon

Pu'u Pehe or Sweetheart Rock

Our last stop before returning to Maui was the back side of Pu'u Pehe or Sweetheart Rock. By this point, many of us were cold and tired, but this did not deter us from jumping in at the fifth snorkel spot of the day. The bay was also deep with very clear water. The reef close to the rock created another sort of pool like that of Honopu Bay, but the ridges on either side of this one did not reach the surface. Just as well since the surge shot me across and back again with little to be done to counteract the movement. I was completely at the mercy of the ocean, but did not feel threatened and just rolled and swayed with it. Sweetheart Rock is shrouded in a tragic history. It is said a young warrior of Lanaʻi named Makakehau or "Misty Eyes” gained his name because his love was so beautiful, she blinded him. Due to Uaua's exquisiteness,  the warrior was concerned she would be coveted by other warriors and wanted to keep her to himself. One day in search of water, Makakehau left his love in the shore cave Malauea. It was Kona season at the time, and as the wind and waves picked up, Makakehau knew his love would drown in the cave. Upon his return, Makakehau fetched his deceased love from the cave and brought her body to the top of Pu'u Pehe where he buried her in a tomb. After placing the last rock, he jumped from the rock to his death. Today, one can make the short hike up the ridge leading to Pu'u Pehe and see the fabled rock tomb.

Photos courtesy of Kate Middleton


Sanguine yet satisfied, we all filed back onto Trilogy Elua for our return to Maui. We did not want the day to end, but all the sun, swimming, and sailing had fulfilled our sense of adventure for the day... Until we spotted something red in the distance bobbing in the channel and decided to check it out. On closer inspection, we found a bunch of balloons that had clearly flown from Maui, landed in the ocean, and drifted to its current locale; approximately six miles from Maui's shore. Definitely, something to consider next time you are looking for party decor. Before a poor unsuspecting turtle or other marine animal had a chance to ingest them, we scooped up the bunch of balloons to dispose of on land. Whether mauka or makai, there are no vacation days from our jobs as ocean stewards and exploring all the beauty Lana'i had to offer solidified our commitment.

Photo courtesy of Captain Riley Coon


A HUGE mahalo goes out to Trilogy Excursions for providing this once in a lifetime opportunity for our staff. As you can see, Trilogy is committed to educating its employees and exposing them to new experiences. Circumnavigating Lanaʻi not only preserves the history of the island by sharing its stories, it also builds enthusiasm amongst the team. We hope you get an opportunity to experience that enthusiasm on your next Trilogy tour. 

Dolphin escourt for the return to Maui. Video courtesy of Kate Middleton

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Group shot. Photo courtesy of Jamie Kleinhenz

Many of the stories here are oral and have been fact checked utilizing The Lāna'i Culture & Heritage Center website: The website was developed through a partnership of the Lāna‘i Culture & Heritage Center and Pūlama Lāna‘i

The other major resource for this post: Hawaiian folk tales; a collection of native legends by Thrum, Thomas G. (Thomas George), 1843-1932 through the website The book can be read at

Written by Kate Middleton