Kailua on Oahu – The Hawaii Town I Dream of Living In

From the moment I first saw it, way back in 2001, I knew that I wanted to live in Kailua. Who wouldn’t want to live there? Gentle trade winds, sandy beaches, lush picturesque mountains behind, and a laid back beach town atmosphere that seemed to have come right out of the movies. The first time I saw it, I wasn’t a tourist, I was breaking up a concrete driveway for my then boss with a pick and shovel for $10 an hour.

After nearly killing myself to get the job done, my boss suggested that I walk down to the beach and take a swim – her house was just a few blocks away from Kailua Beach Park. I walked down there – saw the picture perfect islands beyond the picture perfect sand beyond the picture perfect grass rimmed with picture perfect palm trees and then I got in the water and it was love love love.

Two years later when I moved back to Oahu from Kauai and decided to stay on Oahu, I rented a storage unit and mailbox in Kailua – my first step towards living there. It took a year of living in my van but finally, I found a good job and an apartment in Kailua – a large studio for the then princely sum of $750/month.  It was three blocks from the beach.

 I dream of my daughter riding her bike in Kailua, I dream of living close to my old studio there, but the cheapest small studio I could find was now in the range of $2000/month and there was no way that I could afford it. The prices in Hawai’i have more than doubled in the last 10 years – for housiing and for everything else- and there is no way to live in Kailua, at least not for now, not as an Oahu Tour Guide  – which is pretty sad, actually.

What changed in Kailua (and Hawai’i for that matter)? I can see several things. First of all, President Obama really put Kailua on the map when he took his family vacations there…next was the extreme concentration of wealth after the great recession- the rich have consolidated their holdings and Kailua is the perfect place for a rich person’s vacation home – finally, and perhaps most importantly – AirBnB and similar peer-to-peer vacation rentals have made renting an apartment or house for the night more profitable than renting it for a year – landlords have converted almost wholesale to hoteliers with managed housekeeping and outsourced concierge.

Kailua is a place where you can live if you lived there before all of this or if you have extreme wealth – but other than that – there aren’t a lot of good jobs there, the commute to jobs in town is longer than necessary, and frankly, the landlord class has determined that temporary residents increase their wealth more than long term. All of this, of course, has driven the real estate prices sky high – not just in Kailua but on Oahu as a whole. Median price for a single family home is in excesss of $1 million and median price for an apartment is over $800k – which means there is a lot of competition to buy the very shitty properties that clock in under those numbers….I don’t have the data on who the owners of real estate are in Hawai’i, but when you take out the military (which owns a huge amount) and organizations like Kamehameha Schools, Bishop Estate, and Campbell Estate – what you are left with is ultra-rich absentee landlords – and they have  priced nearly everyone out of paradise – not just out of Kailua, but out of Hawai’i in general.

We manage to survive on my tour guide wages – but it’s not easy. I sell at the Aloha Swapmeet, sell at the antique shows, cruise garage sales and thriftshops in my off time, and sell on eBay too. I’m always doing something to raise money to pay our bills – and it’s worth it even if we can’t afford to live in Kailua -yet. But my heart still lives there. I go there every chance I can. I still get my mail there with a rented post box. So, my address is in Kailua even if my apartment isn’t. Using my post box, my business is actually based in Kailua as well. I don’t plan on changing that – but I do plan on changing my income at some point and moving my family to Kailua. It will happen.

Flashback Friday: Returning to Oahu After a 9-Year Trip Around the World

In 2008, I graduated from the University of Hawai’i at Manoa, moved out of my apartment in Manoa, said goodbye to my sweet landlady Mrs. Arizumi and then I stayed in a Waikiki hotel before flying to Portland, Oregon for Christmas. From there I took trains across the USA, flew to Europe, took a ferry to Africa, hot air ballooned in Turkey, rode horses to the pyramids, hitchiked into the Korean DMZ, hitchhiked and walked across Canada, sailed in the Aegean, got married in the Sahara, emigrated to California with a foreign wife and child, started and sold an antique shop and a newspaper in Oregon, went through the citizenship process with my wife as she became a naturalized citizen, and then after nine years of being away, I came home and got things ready to bring my wife and child back to Oahu.

It was the completion of my trip around the world. I arrived back on Oahu in June of 2017. I rented a car, and then I drove to the SGI culture center on the Nuuanu Pali Highway where I chanted Nam Myoho Renghe Kyo in gratitude for returning home and the completion of my adventure. After that I drove to Kailua on the windward side of the island and went directly to Ninja Sushi where I ordered the meal that I’d thought about constantly but not had since 2008. A Shogun Dunburi from Ninja Sushi.
It was as delicious as I remembered. The years had not magnified it. I was not disappointed. I ate every bite.

There were lots of new expensive houses. I had thought that perhaps I would move my family to Kailua when I brought them to Oahu a few weeks later – but Kailua seemed to have moved out of our economic range – for the moment. Still, I stopped at my favorite beach park and bodysurfed a dozen waves before sitting on the sand and staring out at the Mokulua Islands in rapture.

I looked through Kailua a bit noting that Kimo’s Surf Hut still survived but had been moved because a shopping center had gone up filling that block. Daiea – the Korean Superstore had disappeared – replaced by Target and Safeway. Other loved businesses had also disappeared…but there were new ones. Then I drove around the South Shore of the Island with Hawaiian myth, story, legend, geography, and more flooding into my brain. All that I used to share as a tour guide started to return as I passed Pele’s chair, Rabbit Island, Makapu’u, and Koko head. I was hit hard with memories of my epic walk around the perimeter of Oahu as I saw familiar stones, heaiau, and landscapes. I drove to Waikiki, remembering the traffic, the roads, and the feel. One sad note – I saw far fewer people stopping to let pedestrians cross traffic than I used to. Especially in Kailua where people seemed surprised as I let them cross and an impatient driver even honked at me. My hotel, the Waikiki Ambassador was a fake internet bargain. Comfy bed and pillows but a concrete box with 1980s furniture and no real comfort. It was on the opposite end of Waikiki from where I began at the hotel named for deposed Queen Liliuokalani.

I drove to Waikiki and paid my respects to Duke Kahanamoku and then went up to Manoa and visited Mrs. Arizumi and her daughter Clare and her little dog Choo-choo. Mrs. Arizumi must be near a hundred now – maybe older, I don’t know. She is still sweet and I was hugged and welcomed back like a part of their Ohana. After that I returned to Waikiki and took a long walk. Being a person who doesn’t enjoy crowds or shopping, I shouldn’t love Waikiki, but I do. My whole heart does. This is home. As I stood by a favorite Niu next to the jetty I leaned against it and I swear this old coconut tree was happy to feel me leaning against it again. The waves were welcoming me home and the sunset kissed me and welcomed me home. Yes, I was home and after looking all over the world – I know for certain that Hawai’i is the best place in it. This adventure had come to an end.

And then, on that day, a new adventure began. Home is where the heart is. My heart is always here on Oahu.