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Kailua, Hawaii – Our Favorite Spot

Will it be as good as we remember? The question ran through our minds as we headed toward Kailua, Oahu, Hawaii. We lived there for three years from 2011 to 2014, and our memories of it are fantastic. Kailua still ranks as one of our favorite places on the planet. A walkable, moderately sized town framed by tropical sheer mountains to one side and a long white beach on clear turquoise water to the other side, Kailua may be as good as it gets as a place to live. If you have the money. It helps that we did, and we lived in a gorgeous apartment just steps from the water. But would a return trip confirm our memories or prove that the mind can mistake nostalgia for reality?

We went on a date to one of our favorite restaurants, Monkeypod, and the view was as golden as the Mai Tais!


Our car was waiting for us in the airport parking lot. We rented a Nissan Leaf (an electric car) from Turo, a car-sharing service to try out this new company and see how we would like driving electric. [The Turo rental was inexpensive and easy, and the car was great, so our experiment was a success. Save $25 on your first rental! We will also get a discount on our next rental. We recommend the service and appreciate you using our link!]  Heading out of Honolulu we hit rush hour traffic, but nothing could dampen our excitement at being back on the island.

We pulled up to the drive of our friends, Brian and Etta (and their baby), and were soon chatting on the couch of their island home. Our first night back in Kailua passed with pizza, Oahu beers, red wine, and a game of Yahtzee. When we went to bed tired and happy I looked up through the window. A monochrome sky of stars, clouds, and palms greeted me and I drifted off to dreamland happy to be back in our spot.

We woke early to hit the beach with some of Brian’s surfboards. The walk from their house is a short ten minutes, but with a 9’6” surfboard my arms were already burning. Without delay, we hit the water and paddled out to Castles, the Kailua surf spot. Trying to find a good spot we paddled around, and around, and around. Zack would look back and laugh as I dug in and tried to keep up. I joked back that he would have us paddling to the next island over before we were done. It was awesome.

Being out on our favorite water again was magnificent. Kailua Bay is crescent shaped with two striking points defining it and the Koolau Mountain range rising in velvet greens behind the palm covered town. The water is warm and usually clear. On this morning, it was a bit green, but I guess we can put up with that… Zack caught a few waves. I only caught one on my belly, but it was still a great time.


Soon after we arrived, the Polynesian sailing canoe Hokulea made her homecoming voyage into Honolulu after a three year around the world trip using traditional Polynesian sailing techniques. I was interested in the journey, and as it turned out Brian and Etta were planning to go to the homecoming. Perfect!

The crowd for the homecoming was dense and happy. Five other boats came in before Hokulea, and each received a lavish welcome. Finally, Hokulea glided into the harbor to cheers and horns. People were exuberant, proud of the Hawaiian culture and for what Hokulea stands. The motto of Hokulea is “Malama Honua,” which basically translated means, “to care for our island Earth.” Of course, most translations are a bit more complicated and according to the Hokulea website, it really means to take care of everything, each other, earth, living things, cultures, and communities.

Hokulea Homecoming
The Polynesian Fleet
Hokulea Homecoming
Hokulea Under Sail Coming Home (Diamond Head in Background)
Hokulea Homecoming
Traditional Sailing Craft Against Modern Honolulu

Taking care of Earth is taking care of each other. They are one in the same. To be indifferent to Earth is to be indifferent to each other. It’s simple and beautiful. Watching the Hawaiian community acknowledge their past traditions and cultures while looking forward was inspiring. I admired how the homecoming honored a heritage but didn’t cling to or long for the past. It used the lessons from that time to find solutions for a modern world. You can read more about Hokulea and its epic adventure at the official website.

Jumping Out of a Plane

We had discussed skydiving in Hawaii when we lived there, but I was still apprehensive. After we decided to go to Hawaii this time, I suggested it and Zack immediately agreed. So, we booked our jump and drove up to the North Shore. About twenty minutes after arriving we were climbing into a Cessna.

Once the plane was full, we took off and in just a minute one of the instructors opened the garage style door letting in a welcome rush of cool air. The pilot made wide circles over the North Shore ascending. It was a sunny and bright day with some puffy clouds dotting the sky. As we approached jump altitude, our instructors joked and clipped us to them.

The plane leveled out, the little light turned green, and people began disappearing out the door. We shimmied on the bench toward the door awaiting our turn. As each couple went the plane felt lighter and lighter. Zack and I were last. He went, disappearing in a split second.

Zack and the Northwest Point of Oahu

We approached the door in the empty cabin and I looked down. Below us lay ocean and coastline, North Shore Oahu looking absolutely stunning, and 14,000 feet of air. The beauty of it seemed to almost fill my mind. Almost. Rushing cold air reminded me of the jump and the thrill came. This is against the natural laws my body knows after millions of years of evolution, but somehow so awesome. The instructor rocked back and forward once, twice, and jumped.

Freefall. I let out what had to be an ear-piercing scream; it was easily swallowed by the roaring nothingness around us. It was so loud! The sensation of falling to the earth was thrilling, amazing, exhilarating, everything. I was smiling and screaming soaking up every second. I felt so small as the earth rushed toward me, like a fly it could flick off if it so desired. My eyes watered, I could barely keep them open and the crashing waves below, blue to white to green, turned blurry. My mouth became dry, stuck open in a now silent wide awe-filled grin.

Um, OMG?

A quick flapping sound, a jerk, and silence. The parachute had opened. Everything slowed way down, I licked my dry lips and blinked away my tears. After loosening our connections the instructor put the risers in my hands and let me steer. We did a spin over the beach and made our way back toward the airfield. We lined up to the runway and approached not unlike a small plane, except that we were only two humans under fabric.

Floating over North Shore

Soon the ground was closer, the people distinguishable, and just like that, we made a gentle landing with a few steps in the grass. Sixty seconds of freefall and five minutes under the canopy was over so quickly! Zack and I high-fived and kissed and beamed and headed in to finish the admin still flying high.

What next? Well jumping out of a plane made us hungry, so we stopped at the Dole plantation to get some pineapple whip before heading back to Kailua Whole Foods (the best Whole Foods) to pick up lunch before spending another afternoon hanging out with friends. It was a great Hawaii day.

Pineapple Fields
Inland Oahu – Pineapple Fields


The house was full with Zack and I visiting and our good friend Andrew also in town, making do with the couch. Brian and Etta were super gracious and let us essentially take over their house, use their surfboards, and eat their food. One Saturday, Zack, Andrew, Brian and I got up and headed to one of the beaches on the Marine Corps base. Brian, Zack, and I headed into the waves to surf and Andrew set up shop with his book on the sand.

Zack raves about the two surfing spots on base, but I had never been as they can have bigger waves and frankly I was chicken. But sometimes time away from something can be a good thing and I felt ready to brave the waves at Pyramid Rock. As Zack and I headed out, though, I was questioning this decision. They seemed a lot bigger in the water and I wondered how I would even get past them let alone get back in!

This was a lull, I swear!

A leash broke, Brian found something in his truck to fix it, and we went back out again. This time we made it past the whitewash and out to the lineup. It was just the three of us. The water was deep and dark blue-green beneath us and clouds were still perched up on the mountain tops. One of the awesome things about surfing in Hawaii is that even if you don’t catch a wave, heck, even if you don’t go for a wave, the views are stellar. Just being out on that water is lovely.

The sharks like it, too. One of the reasons I had been afraid to go to the base surf spots was all the stories I had heard about shark sightings there from the people at work and Zack. On this peaceful morning, every shadow and movement had me jerking my head around, sure they were underneath watching and waiting to make their move. Eventually, I relaxed, no shark sightings that day.

Zack and Brian caught lots of good ones. I went for what felt like lots, but mistimed most, or was in a bad position on the board, or just wiped out somehow. Boy, it was hard work, but it was fun. After hitting the bottom a couple times and knowing I would be fine my confidence grew a bit and I tried for more waves and larger ones. I didn’t catch any, but toward the end a couple caught me and those rides were reward enough. As I approached, Zack ran up beaming. He threw his arms around me in a huge hug, picked me up, and kissed me standing there in the lapping shore. Well, cool. I guess I did alright.

Hiking Oahu’s Trails

As much as Hawaii is a surfing mecca it is also a hiker’s dream. One morning our little motley crew rose early and hiked to the Lanikai Pillboxes to watch the sunrise. The Pillbox Hike is an easy twenty-minute hike to old WWII concrete lookouts, nicknamed pillboxes. Facing east, the pillboxes have clear views to the sun rising over the Pacific and the tiny Mokulua Islands sitting just off Oahu.

We all made our way up and found a spot on the boxes to watch the show. Chris, another of the old friends, broke out a bottle of champagne and passed it around. It would have been perfect save for half the champagne getting spilled, but it was still rather great.

Pillbox Hike
Relaxing at the Top
Pillbox Hike
Sunrise over the North “Mok”
Pillbox Hike
Graffiti with a Message
PIllbox Hike
Morning Glow
Pillbox Hike
Looking South to a Rainshower
Pillbox Hike
Front Row Seats
Pillbox HIke
Hiking in Kailua
Pillbox Hike
Lanikai Glowing Golden
Pillbox Hike
Graffiti Art
Pillbox Hike
One by One

After breakfast, Andrew, Hannah, Zack, and I set out for another hike, the Olomana Trail, known locally as Three Peaks. Once again, the vistas were fantastic. Although we only made it to the first peak the views stretched out in 360 degrees below us. Kailua sat nestled in the flat land near the water and the mountains rose majestically, as usual. Andrew picked up some smoothies afterward and all was right with the world.

Olomana Trail
Go Up
Olomana Trail
How far have we gone?
Olomana Trail
Andrew Starting up the Rocks
Olomana Trail
Peaks Two, Three, and Koolau Range
Olomana Trail
Enjoying the View
Olomana Trail
Peak One
Olomana Trail
Olomana Trail
Attempting a Trick Shot – We failed, but what a smile!
Olomana Trail
Friends who hike together, sweat together…

Hannah had just moved to Hawaii and was eager to try everything, every hike, every beach, and surfing. Too lazy to make the drive to Waikiki, Zack and I were going to go surfing one afternoon at Kailua Beach and invited her. Kailua Beach isn’t a surf spot, the waves are short and crash right on the beach. However, it’s beautiful and it’s where Zack and I both have learned a lot and had tons of fun right in our back yard. After all, they are still waves.

Zack gave Hannah a mini lesson while I played on the same board I had used at Pyramid Rock, shaped by our friend Evan, who runs his own furniture and board shaping business. The board was great for me and I had more success the second time with it in the easy-to-time shore break. I felt like I was zooming through the water; I was getting up and enjoying myself which I think, is the point.

The normally clear water was a bit milky and green, but we kept on in the water anyway. All three of us separately noticed things stinging us. Eventually, someone said something and we all commiserated. Hannah was a great sport, but we went in after some rough and tumble waves. Zack had a sting in his shorts, so we made quick work of the walk home!

Returning to Friends

Returning to Kailua felt a little bit like going back to another life. We saw lots of old friends and enjoyed catching up with them. Being back in the military tribe from a few years ago was a bit peculiar. Many friends were in town for one reason or another, and to be all together in our favorite place made the visit even more gratifying. Everyone shared one common time together, and everyone’s lives have spread out in different directions since. Old stories were shared once again and new stories were added.

When we weren’t catching up with friends, we were hiking, surfing, trying out the many new beers, running errands in big American stores, and watching clips of Moana, the Disney movie. Essentially, we were living the life.

Often it hit us just how different our everyday life is now and how much has changed, but mostly we just enjoyed feeling happy in a warm blanket of friendships that are just always there, that don’t need to be defined by anything other than the present. And that is when humans really shine. Cheers!

Kailua Beach
The Best Beach
This 100ft piece of shoreline remains one of my favorite places. 
Kailua Beach
Memory Lane – The Old Home Beach at Low Tide

Leaving the Pacific, Again

Soon enough, our last night arrived and we all sat down to watch Moana (all the way through this time). It hit me that we would once again leave the Pacific the next day after months of island life. Some people complain about getting island fever, but neither of us has felt this in all our time living in and exploring Pacific islands. Hawaii is a fantastic spot for just about all our hobbies and we love the culture. We like the isolation from the mainland, the feeling of nature being part of our life, and the constant reminder of how small we are in a big world in a vast universe.

When we left Hawaii years ago, I felt a heavy sadness at leaving what had become home. More than anywhere else, we had built a life there that we loved. We knew that we would never have that specific experience again, and that thought was depressing. Years later, I still felt sad at leaving. But not depressed. Now we know – the return trip confirmed our feelings on Hawaii. It may be different for us when we return, but it will always be Hawaii. It wasn’t just nostalgia for another time in life, Hawaii is marvelous. And we’ll be back.


Check out our video for skydive footage, peaceful sunrise views, and more!

© Cheers Life Partners 2017

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The Cheers Life

We make every day worthy of a toast! We quit our jobs in October 2016 to travel the world full time.

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