When I moved to Hawaii – I had $100. I booked a dorm bed into the Polynesian Beach Club Hostel in Waikiki for seven nights and bought some rice and cheap veggies in Chinatown. During the next week, I ate rice and beat the streets looking for a job. I found a job painting houses and then moved into a longer term hostel down the road called the Beachside Hostel. I got a discount for waking up early and cleaning up the common areas.
Painting houses wasn’t very fun and while the owner of the hostel I was in was giving me a discount, she wasn’t a particularly nice woman – so my life wasn’t the Hawaii dream I’d been expecting. I’d made friends with some of the people who worked at the Polynesian Beach Club Hostel and was down there when the owner came in and told everyone that the manager had stolen a bunch of cash and left the island. I’d talked with the owner a few times in the past and had a friendly relationship – I volunteered to be her new manager. She agreed. I quit the painting job and moved into the manager’s apartment. My Hawaii dream life was taking shape.
A little over a year after I started, she took a month long vacation and left me to handle everything. It all went good except I’d gotten a dog while she was gone. She told me to get rid of it. I’d grown attached and honestly, I don’t respond well to orders. During her absence a shady character who was opening a new hostel on the windward side had been trying to recruit me to come help him build his place. She gave me the ultimatum about the dog and I resigned and moved to the new hostel “Countryside Cabins” in Punalu’u.
Punalu’u was AWESOME. We built this amazing country Hawaiian hostel where our guests regularly decided to skip their flights home and stay longer. We had bonfires every night, we had an outdoor kitchen we cooked communal meals in every night, we integrated with the local Hawaiian community and they taught us how to cook in an imu, spearfish, hunt pigs, catch prawns, and much more. It was like a Hawaiian dream. Then it became a little like ‘The Beach’. The owner was older and single and all of us young guys were regularly hooking up with our guests and he wasn’t. He started drinking more, getting sort of abusive to the staff, and frankly, being a dick. People stopped staying longer. It was unpleasant. Some of the locals had developed some heavy ice habits (smoking meth) and there were a couple of scary incidents. The owner kept driving away our guests and then when I took issue with it – he drove me away. We’d made a gentleman’s agreement – I would come, help him build, recruit a staff, and set up tours and activities. I would be paid a salary and the tour revenue would be mine. He renegged. When I complained he said “What are you going to do? You have a dog and you don’t have anywhere to go?”
I gave my dog to a local guy who liked him and I put my things in a storage locker at Kailua Mini Storage. Then I bought a ticket to Kauai where I hiked out the 22 mile trail to Kalalau where I set up a camp in the jungle and stayed in solitude for a couple of weeks before I met some of the other outlaws out there and began to take part in the Spiritual Pizza parties, pakalolo sharing, and heavenly communal living in the valley.
When I finally hiked out of Kalalau, I was in love with Kauai. I got a job at the Blue Lagoon Hostel in Kapa’a and then got hired as a kayak river guide at Paradise Kayaks. I bought a VW van and lived on the beach in Kapa’a next to the Kayak shop. For the next two years, I was a river guide – then I fell for a flight attendant and went to Portland where I published Rough Living: Tips and Tales of a Vagabond before coming back to my senses and returning to Kauai. After that I took a trip to the Philippines and when I returned I decided to live in Kailua on Oahu and write a novel. I bought another van (I’d sold the one on Kauai) and wrote my first novel, Slackville Road. When the book was finished I was ready to do something else. I got a job as a tour guide and limo driver and rented a studio in Kailua. It was one of the best places I’ve ever lived. I began blogging and creating an online used bookstore and everything empire. I was the Chairman of the Fukn Bored and CEO of Fukn Books, Fukn Records, and Fukn Clothing. I met an amazing woman, we fell in love, we got engaged, and she went to Africa to help the people of Sierra Leone. Then we mutually fucked everything up. For the next couple of years we tried to fix things but were unable. We lived in Lanikai and then on the Punchbowl. Finally, I enrolled at University of Hawaii and rented a studio in Manoa. Our relationship never recovered – which is a pretty huge bummer. She was one of the most awesome people I’ve ever known – and today, we’re not even in contact. I miss her friendship.
Anyway, I did my best to make myself important but school took all of my energy and the Fukn Empire began to fall apart. I put my energy in becoming the managing editor of Ka Leo, the University of Hawaii student newspaper, the president of the Honor Student Organization, an Osher Scholar, the President of the UH Sierra Club Chapter, and a dozen other things. I made student films, wrote an undergrad thesis, and graduated with honors. That was December of 2008 and the economy was fucked. So I gathered what money I could, sold all of my possessions, and decided to take trains across the USA and then go travel the world – that’s when Vagobond.com was born.
Kapa’a, Kauai
Kapa’a is a small town on the East side of the island of Kauai. It’s beautiful and not really a big tourist destination – at least it wasn’t when I lived there, mainly because there were few hotels there. The population is about 10,000 today – to the south is the Wailua River and the once famous Wailua Beach – home to the destroyed Coco Palms Hotel that was devastated by the 1992 Hurricane Iniki. The Coco Palms was where Elvis loved to stay in Hawaii, many movies were made there. Frank Sinatra stayed there too. The Wailua River is a popular kayaking destination. There are waterfalls, a Hindu Temple, some surprisingly tasty restaurants, and large empty stretches of beach nearby.
Over the past year, I’ve written a large number of posts that detail the different neighborhoods, cities and towns of Honolulu – which includes the entire island of 
Kahalu’u means diving place. All told there are about 2300 people in Kahalu’u. Most of them are Chinese and Hawaiian descent people. This was an area where many Canton Chinese settled in the mid 1800s. The most famous resident was probably Senator Hiram Fong. He was the first Asian American to be a U.S. Senator, the first to run for his party’s nomination for President of the USA, and to date, the only Republican Senator to ever come from Hawaii. I used to take people to 
Past the Kualoa Ranch, you will come into sweet little Ka’a’awa. K’a’a’awa means Wrasse. About 1,379 people live in Ka’a’awa. Nicholas Cage’s character gets stuck there in the movie ‘Honeymoon in Vegas’. You can bet some pretty decent Southern BBQ at Uncle Bobo’s restaurant. I love the beaches in Ka’a’awa. They are narrow strips on the ocean side of the road but rarely crowded and usually the people there are local people fishing, swiming, and talking story. On the North Side of Ka’a’awa you will find the popular Crouching Lion hike behind the now being refurbished Crouching Lion Inn.
Punalu’u means ‘coral dived for’. It is home to about 881 people – and is where some of the oldest inhabitation remains found on Oahu are located. Ching’s Market and Kaya’s Market are the only two stores. These are windward everything stores and carry everything residents might need including food, fishing supplies, hardware, and 5-toed reef shoes called tabies. The Kawananakoa Beach House is located here – it was the summer home of the Kawanakoa Family (heirs to the Hawaiian throne). I lived in Punalu’u back in 2002. I managed and helped build a hostel called Countryside Cabins – it was an amazing period in my life and I learned much of what I love about Hawaii from the residents in Punalu’u who taught me about aloha, the Hawaiian way of life, and local Oahu culture. Punalu’u has fallen on some fairly hard times these days. The cabins fell into disrepair when I left and eventually folded. You will find the first of the 