Finding Adventure in Hawaii by Sherry Ott

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Each island in Hawaii has it’s own personality and I’ve been lucky enough to visit them all. And I haven’t just visited them; I’ve had many nail-biting adventures on them! If you are an adventure junkie or simply looking for something unique to do on your Hawaii vacation, then check out my favorite adventures on each island!

Big Island Cattle Drive

The rain was pouring down, and the wind whipped around me. The skies were filled with gray low hanging clouds hiding the beautiful pasture views from me. I think about other tourists out on the beach on the sunny side of the Big Island, but I just had to be different. Now I’m on top of a horse named Red, slightly exhilarated and slightly nervous. I can hardly believe that a beginner rider like myself is about to embark on a cattle drive with absolutely no tourist fluff to it. But this is where I like to be, on the edge; the edge of excitement, nervousness, and newness – this is real adventure.

Big Island Hawaii Adventures 2

Pa’akaula, our Hawaiian cowboy guide, works with us for the first 30 minutes on horse guiding and control. I learn how to actually be the ‘master’ of Red – and I have a rush of excitement come over me realizing that I am really horse riding – as opposed to just doing a tourist trail ride! Pa’akaula motions for us to gather up near the rest of the cattle; it is time to get down to work. The wind is whistling, the sky is dark and the cows look as if they really don’t want to move. He gives us a little advice about how to use the fence line to keep the cattle ‘pinned’ in. He also demonstrates how to be vocal in order to get the cattle to move with a loud “Ya!”. Pa’akaula looks at us each slowly and says, “Ok – this is your adventure, good luck!” and walks away on his horse.

Big Island Hawaii Adventures 1

After trial and error, and some additional help from Pa’akaula (no he didn’t really leave us!), we managed to herd the cattle into their pen and not lose a stray! Success!

Catch a Wave and Learn to Surf in Maui

Maui Hawaii Adventures 1 - me surfing

Could they make this 43 year old Midwesterner a surfer girl? As someone growing up in landlocked Peoria, IL – I never really became one with the ocean, it’s waves, currents, or sea life. Therefore, I was nervous about surfing – yet the athletic overachiever in me was pretty stoked to try.

Maui Hawaii Adventures surfing dog

I looked over and saw that our instructor’s dog was on a surf board in the water. If Maui Surfer Girls could teach a dog how to surf, then I had hope! Luna, the surfing dog, is just one of the many things that make Maui Surfer Girls unique. The MSG mission is to “empower girls through the sport of surfing” – and they take this mission seriously. They run surf camps for girls each year where they do more than simply surf – but also focus on building self-esteem and confidence for teen girls.

Maui Hawaii Adventures  - teaching technique

First, our instructors demonstrated how to surf on land. They talked about centering on the board using yoga terms and positions. When broken down into the steps it actually seemed pretty simple. However, once in the water, things got a bit more complicated. I laid there on the board tense and poised. I could first hear it – the sound of the wave coming behind me, then as I paddled furiously I could feel it; a swell lifted me up. I heard Sharky yell “Now!” I quickly tried to go through the yoga poses in my head and before I knew it I was wobbling on two feet trying to adjust and find the center of the board. I didn’t last long, but I got the feel of it. I surprised myself by getting up on 2nd try – and you can too with a little instruction!

Combining Hiking, Adventure, and Photography in Kauai

Kauai Hawaii Adventures 2

The premise of the workshops was to take people out to lesser seen and photographed remote areas of Kauai and work on specific photography skills such as night photography, landscapes, photographing waves, long exposure waterfalls, and they even covered post processing. Two photographers, Patrick and Matt, who live on the island, run the workshops. They know exactly where to go to get great shots that aren’t your run-of-the-mill Kauai photography. Many of their workshops included some pretty adventurous hiking to remote areas, which was just what I was looking for.

Kauai Hawaii Adventurs me hiking into the waterfall

It didn’t take long for Patrick to get me out of my shooting rut and get me using new settings on my camera that I had neglected. The next day after a heavy morning rain we decided to hike to Ho’opi’i falls. Patrick warned me it would be muddy, but worth it since the water would be flowing heavily over the falls. This was a chance to work on my long exposure – there were 2 waterfalls we were going to hike to before nightfall. The hike through the dense forest was really fun as Patrick got me closer to the waterfalls than I ever would have ventured myself. He knew all of the ways down and around that made for great shots.

Kauai Hawaii Adventures 1

They also took me out to a little known lighthouse by the airport so we could do some long exposure night photography and light painting. With headlamps and flashlights, we hiked out onto the rocks as the waves crashed spraying us with water. We set up our cameras on tripods and waited. We were waiting for the planes to land to get a long exposure light trail over the top of the lighthouse. This was a simple waiting game that we had to test out a few before we were able to get the exposure and timing right. This was the perfect combination of adventure and learning and Patrick and Matt will certainly take you off the tourist trail!

Off-roading Through the Unique Landscapes of L’anai

Lanai Hawaii Adventures 1

Lana’i has over 100 miles of unpaved roads which means that the only thing that the rental car agency in Lana’i rents is jeeps. Beat up jeeps. Really beat up jeeps. The agent gave me a little map of the island titled Jeep Safari that sort of looked like a treasure map. She explained that they didn’t offer insurance, which seemed slightly surprising for a rental agency – I wasn’t sure if that meant even insurance was too risky or that they just didn’t care.

Lanai Hawaii Adventures 2

I drove down the last of the paved roads down the north side of the island which is known for it’s dry climate. This part of the island only gets 10 inches of rain a year. We headed to Shipwreck Beach with the top down and the wind in our hair. We left the shipwreck and drove back up toward the center of town and took a red dirt path that led out to Garden of the Gods. This road was much dirtier and bumpier than the beach road – which basically meant it was more fun! We drove through old pineapple plantation fields and forests making a stop at Garden of the Gods. Don’t let the name fool you – there’s nothing lush and green – this is a rock garden – formed by wind erosion. The alien like landscape is stunning to take in.

Lanai Hawaii Adventures Garden of the Gods

We continued further down a deteriorating road and finally came to Polihua beach where the road ended and a sign instructed us to park our rental vehicle. Now this was paradise – a huge beach all to ourselves.

We sat and took in the view with the smell of salt air and crash of waves in the background knowing that the real adventure would be to actually make it back to the rental agency before sundown.

Descend the Steepest Sea Cliffs in the World in Molokai

Molokai Hawaii Adventures  - Kalaupapa Park

I held on tight as I descended 1,700 feet on 26 narrow switchbacks down the steepest sea cliffs in the world. Luckily, you don’t have to do this alone; you have help – a mule. At the end of the 2.9 mile trail you enter the formerly forbidden village of Kalaupapa which was established in 1866. There we boarded a rusty old school bus and toured the old leper colony learning about the tragic history of leprosy, their attempt to control it from spreading, and the legislation around it. Law dictated that infected people in Hawaii were shipped to Kalaupapa to live out their life and never to see loved ones or civilization again.

Molokai Hawaii Adventures 1 trail switchback

My mule, Koa, liked to swing wide in the switchback turns; I wasn’t too fond of this. However by turn #11 I had gotten used to it and learned to simply sit back and trust Koa. It did take a decent amount of Zen and core strength to just go with the flow and rock along with the mule in every turn. Once I found my Zen while teetering on the ledge, I could take in the spectacular views descending the sea cliffs.

Molokai Hawaii Adventures 2

The trail down the seacliffs is the only way into the National Park and Historic Sight of Kalaupapa, but it’s worth every wobbly turn on Koa!

Swim with Sharks in Oahu

Oahau Adventure - me getting into tank-1

The big warning about this tour was not about the sharks, but about seasickness. We had to ride in a small boat 3 miles away from shore, which equals a pretty rocky experience; I came prepared with Dramamine.

Oahu Hawaii Adventures 1 sunrise on way to the cage

Our Hawaii Shark Encounter guides lectured us on safety instructions while we drove the 3 miles out to the floating cage. The morning was gorgeous and the sun was just starting to rise. My coffee had kicked in and I was feeling alive as the warm Hawaiian sun hit my body. Calm, cool, collected. The guide said that only 5 of us could be in the cage at the same time so we would need to go in two groups. “Who wants to go first?” he asked. I am not necessarily brave or daring, so I’m not sure what came over me when I said, “Me!”

Oahu Hawaii Adventures Me in shark cage

I slowly descended down the ladder into the warm water, steadied myself on the rungs of the cage and put on my mask. Simply stepping into the cage and water got my adrenaline pumping. There they were, staring back at me. Galapagos and Sandbar sharks calmly swam around the cage circling around the boat and us; there were about 12 of them and 5 of us. The biggest ones seemed to be over 6 feet. I was surprised at how big they were when they swam underneath the cage. They weren’t frenzied or menacing, but instead they seemed to simply be going about their business. They were sleek, and moved about fluidly about the cage, staring at us as we were staring at them. Put this on your bucket list!

About the Author: Sherry Ott is an avid travelers and a contributor for InsureMyTrip. To learn more about her travels, visit

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