Hopeless to Honolulu: My first Solo Trip

I had been reading so much on people who take solo trips, and I got bit by the bug. I was curious; what is so intriguing about going somewhere alone? What the hell do these people do? Do they get bored? I thought of every question that I’m now constantly asked.

I wanted to do something big; go to Machu Picchu, go to Thailand, go to the South of France, but I decided to start “safe” and stay within my own country, but as far away as I could possibly be. After all, I had been on an airplane so many times by myself, what would be the difference if I landed and didn’t know a single soul, right?

I decided on Hawaii.

For the next few weeks I constantly looked at the map of Hawaii. You have to zoom in for a good moment to even realize this place EXISTS. I was loving it. I couldn’t stop researching what to do, what to eat, if it was safe, other women who have ventured out there on their own, and if I was insane.

This was the ultimate test to my budgeting, as well. I didn’t bring any credit cards, I was, to be totally honest, slightly treading water on even paying rent (I had it but I was skimming), but I knew mentally and emotionally it was what I needed, so I figured I’d do it on a budget. I went to Hawaii for six days with $600 (after paying for flights and my stay).

Hawaii is NOT a budget destination.

On the plane there, Hawaiian airlines gave us these cute little pineapple shaped chocolate chip cookies.

Little did I know, I would later have a love affair with these same cookies (more of that later).

I arrived and at the time, it was the bluest waters I had ever seen. I immediately felt a sense of peace and serenity. I think it’s impossible to stare at waters that blue, skies that clear, and glistening palm trees like the ones in Honolulu to NOT feel a sense of relaxation. I headed out to my AirBnb, which was actually a boat that I opted to stay in $70/night. I wasn’t quite ready for hostel life but I was ready for something different (once I was on the island, I will say I was envious of all of the people staying in hostels, though, I am grateful to have said I stayed on a boat in Hawaii).

I got to my boat and realized I highly overpacked. I had one large suitcase and a small carry on. The act of carrying it onto the boat was degrading enough to make me realize it.

I dropped off my luggage, and headed out to the beach. I was about a fifteen-minute walk from Waikiki Beach, the popular honeymoon/tourist destination in Honolulu. I strolled down to the beach and searched for some food. I got some Spam Musubi and fresh pineapple. Feeling jetlagged, I decided to go back to the boat to get some sleep.

Twists to staying on a boat: When I woke up the next day, as soon as I got off the boat, I still felt the motion OF the boat. Apparently, when you sleep, your body becomes accustomed to the rockiness of the waves. It wasn’t the most comfortable feeling, but I managed to deal with it.

I found a diner called Highway Inn Kaka’ako and ordered a loco moco. It consisted of white rice, a ground hamburger patty, topped with a fried egg, and it was damn delicious. The woman working both the counter and the floor was from the Philippines. She was sharp, witty, and strong. I wanted to come back every morning strictly just to see her.

After eating the Loco Moco, I headed out to hike it off at Diamond Head. I didn’t realize Hawaii was so far spread out, and I decided to walk (I could’ve taken the bus, but I chose the scenic route). It was a nice two-hour walk in the blistering sun, but walking along those blue waters, it’s hard to complain.

Once I got to Diamond Head, I bought a giant bottle of water (expensive!) and began my hike. The hike is moderately easy, despite the sun and consistent incline (there are stairs to guide your way up). Once you arrive to the top, like always, the magical views make all of the sweat worth it.

I felt on top of the world. Taking in views like this was exactly why I needed to come somewhere new. That feeling of simplicity; walking for two hours not knowing where the hell you’re going or if you’re even headed in the right direction, working out in the blistering sun, being led to scenery like you’ve never experienced before; I slowly felt my worries shed off of me.

I headed back and I was beat. I took a chance and thought, so far the people are good, so I hitch-hiked! I guess I was on a high. A lovely couple drove me back to Waikiki and dropped me off near the main shops. I stumbled upon a cookie shop called Honolulu Cookie Company. The cookies were pineapple shaped and I immediately realized they were the same cookies from the airplane! I was able to sample various flavors and had the epiphany that I LOVED THESE DAMN COOKIES. Maybe it was the familiar flavors of flying into the unknown, or maybe it was all of the butter and sugar, but I bought more than I could chew (ayo).

I headed to the beach and met a group of older guys who offered me a beer. Why not? I watched them opened it so I was sure I wasn’t getting roofied, at the very least.

They invited me out later and I knew I wasn’t going to go, but I said “alright, I’ll catch ya later” and never gave them my number. #bye

The following day I decided to face my fear of swimming in the ocean. As crazy as it sounds, I’ve just always had an insane fear of sea animals and sharks, but a strong desire to swim in the ocean. I took a bus to Hanauma Bay.

They make you watch a short film on what not to do, primarily focusing on not touching sea turtles and coral. They warned us of jellyfish and what to do if we were stung. After the video, we were able to go in the water!

I headed in and immediately saw some fish. “This isn’t so bad afterall!” I thought. About five to ten minutes into my journey in the water, while I desperately searched for a turtle, I heard the lifeguard blow their whistle.

“Everyone out of the water!”

I basically pushed children out of the way because I thought there was a shark. Turns out 88 people were stung by jelly fish, so Hanauma Bay was shut down for the day. Unfortunately for me, it ended up being shut down for the rest of my time there.

After Hanauma Bay, I headed over to Rainbow Drive-In, as I heard they had great deals on traditional Hawaiian lunch plates. Damn, were they right! For $9, I received a plate of various meats, rice, macaroni salad, and potato salad. The food was SO delicious, I ended up buying a T-shirt, despite my low budget (I couldn’t resist, Hello Kitty was on the shirt).

That night, I decided to go out bar hopping to several dive bars. I knew going to dive bars would be my best bet to meet locals, and save some coin on drinks. I started at Honolulu Tavern, had a few local beers, and this woman asked me to watch her dog while she went out to smoke a cigarette!

I continued to hop all around, at some point being asked to come home with an elderly man with no teeth (no thanks), and ended up at Honolulu Brewing Company where I met these two guys from New Jersey. We started talking about life in New York, made tons of jokes, and ended up going bar hopping together. We played trivia at a WWII themed bar, and they ended up paying for a taxi for me home to my boat, out of pure admiration and resepct that I was traveling alone. This night was the icing on the cake that people are, for the most part, pretty damn kind when they need to be. You put your differences aside, shoot the shit and just get to know one another, and the world is not such a scary place.

I had one day left in Hawaii with not too much money in my bank account, but wanted to try the infamous Koko Head Cafe. I headed down there, ordered the Breakfast Bibimbap and sat at the bar. I ended up sitting next to a rather outgoing woman who was there on a business trip. We ended up chatting for a while and she told me she hadn’t reached her work quota yet, and to my surprise, paid for my brunch! Now that is luck if I’ve ever heard of it.

Lee Anne Wong is the head chef of Koko Head Cafe.

After my brunch, I knew I needed something cheap or free to do. I stumbled upon Honolulu Museum of Art, which also lucky to my surprise, was free!

It was my last night in Hawaii. A new boat-mate had come on board; a 20-year old surfing chick from Australia. We cracked open a bottle of wine, chatted for hours as the sun set, got to know each other, and eventually, we were off to bed.

I woke up the next day and headed off to the airport with memories to last me a lifetime, a heated desire to travel solo, and a whole $20 in my bank account.