Traveling to Hawaii Alone - Kauai Solo Travel
In 2017 I graduated from university at the top of my class. With a bachelors degree in hand, a prosperous future was surely on the horizon. Right…? Wrong! I found myself stuck in a dead-end receptionist job in a small agricultural town. Where was my house with the white picket fence, high-paying office job, and happily ever after? I was engaged to be married, but something wasn’t quite right. So what did I do…? I booked a 2-week solo trip to Kauai - the Hawaiian island known for laidback hippie vibes, chickens, perfect weather, and surfing.
>> Check out my IG reel showing what it was like to travel alone to Kauai, Hawaii here! <<
Checking out the surf conditions with my surfboards at Wailua Beach on Kauai, Hawaii
Booking my first solo trip to Kauai, Hawaii
Booking a trip to Hawaii is something lots of people dream of doing at least once in their life. It sounds like a pretty normal thing to do if you have the money, right? Well… not for this girl. For most of my life I’ve suffered from crippling anxiety, depression, and an overwhelming fear of the unknown. I was not well-equipped nor well-tempered to go anywhere alone; most certainly not to an island in the middle of the Pacific Ocean.
Did I let that stop me…? Almost! But I somehow summoned up the courage to go! I convinced myself that, in order to get out of the rut I was in, I needed to do literally anything other than what I was currently doing. So I packed up my suitcase, kissed my fiancé goodbye, hopped on a plane, and spent the next 22 hours of travel immensely regretting my decision.
Sitting on the grass after my graduation ceremony dreaming of my bright future
Traveling alone for the first time
Three flights and twenty-two hours later I arrived to Kauai exhausted, anxious, and feeling helpless. I arranged a rental car, but it was a complete disaster. If you’ve rented a car on vacation, I’m sure you know what I mean. The island stunk of what I could only imagine was rotting foliage. I lived in a big, polluted city most of my life, so I didn’t know what fresh air smelled like. The Airbnb I booked was a combination of bizarre and disgusting, and the host had picked up a vagabond during her hike and decided he would be better off staying with me rather than her.
So there I was, smack dab in the middle of the Pacific Ocean with no one to turn to for help. My very first solo vacation. I knew I needed to sort myself out and figure out better accommodations because this trip was costing a fortune.
Donkey Beach on Kauai, Hawaii is a beautiful virgin clothing-optional beach
Luckily I had my rental car, which provided me freedom of movement to explore the beautiful island of Kauai (and somewhere to store my valuables away from the vagabond). I soon found myself lying on Poipu beach, remembering that the main goal of this trip was learning to surf. This is how I stumbled upon one of the most amazingly genuine human beings who, unbeknownst to me, would become my surf coach, landlord, roommate, and mentor. Let’s call him Tim.
Laughing at some silly joke on the Makawehi Cliffs of Poipu, South Shore Kauai
I think I’m falling in love
Tim welcomed me into his home just 5 minutes from the beach. He showed me a side of life I had never seen, gave me surf lessons, took me to beautiful places, let me use his surfboards, listened when I needed a shoulder to cry on, taught me valuable life lessons, and introduced me to his friends. I have Tim to thank for easing me into the nomadic lifestyle and helping me build the confidence I needed to be out in the world alone.
All this happened within the first two weeks on Kauai. My plan was to extend my vacation by a few weeks. However, before I could mention this to my employer, I was informed my schedule was being reduced to 16 hours per week (something I couldn’t support myself on). While debating whether or not to ditch this dreamy new island lifestyle and return home, I did what many solo travelers do and fell in love. Oops… (side note, it wasn’t with Tim).
Skateboarding down the Kapaa Bike Path from Kealia Beach on the Hawaiian island of Kauai
How my vacation to Kauai inspired me to embark on a nomadic lifestyle
I’m sure by this point you know where this story is going. Don’t get me wrong, I didn’t break off my engagement and sell everything to extend my vacation on an island in the middle of nowhere JUST because I fell in love with a random dude. Rather, I realized there was more to life than the one I was living. The island way of life was what I had dreamed of and it awakened a joy and freedom in myself I never knew existed.
So I purchased a flight home to break off my engagement. This was a very difficult decision and my guilt alone was unbearable. I packed up a handful of my things and gave my ex-fiancé permission to sell everything else and keep the money. As if this would somehow undo the damage I had done. Luckily my ex moved on and is now happily married to the love of his life! In the end, we both knew something wasn’t right, but neither of us had the ability to end our relationship any sooner. After this short trip back home to Canada, I was soon back on a flight to Kauai, Hawaii to continue exploring a new island type of life!
Me enjoying the sunshine and ocean at the clothing optional Donkey Beach on Kauai, Hawaii
So that’s how my 2 week vacation to Kauai ended in embarking on an exciting nomadic lifestyle which, unbeknownst to me, would completely change my life for the better. If I hadn’t booked this trip, I might still be stuck in an unhappy relationship with a dead-end receptionist job in a farming town - chasing the ‘dream’ of a 9-5 office job and house with a white picket fence. Thankfully the universe had something greater planned for me. I’m now writing this in a swanky Mexico City apartment, happily living my digital nomad life and dreams of travel. Find out how I ended up moving from Canada to Mexico here and stay tuned for more tales of adventure, travel, and heartbreak.
Have you always dreamed of taking a trip to Kauai, Hawaii? Maybe even fantasized about abandoning your dead-end job and unhappy relationship to live your dreams of finally living in Hawaii?
Pin this to your digital nomad travel inspiration board and refer back to it whenever you need a reminder that anything is possible. Even your dream of living in Hawaii!
