The Beginning of the Lady Pirate’s Life

by Jessi Schultz about a year ago in female travel

Living and Sailing on a Boat in Hawaii

The Beginning of the Lady Pirate’s Life

The life and times of buying my first boat (home) in Hawaii.

It seems like a normal routine to live close to or even on the water when living in a place like Oahu, Hawaii. One would think everyone had their toes in the water, alas, the city cries day and night for the attention of those who will listen.

When I arrived many years ago, I struggled to pay the high rent in Honolulu. I worked in bars, late night strip clubs, restaurants with terrible food, and then I left the island for a long time.

I went overseas and saw the Buddhist culture of Thailand. No one had money, but everyone had a smile. As far as the eye could see there was nothing but rice fields and dirt roads where I found work in Thatum, Surin. I was right on the border of Cambodia. Before finding this place, I had been wandering for several months before running out of funds and beginning a short stint as a teacher.

I was landlocked here. It was almost painful to me. I craved the ocean. All I had was a baby Lima bean shaped pool at the school where I taught. I swam there at nights when no one else was there. It made me realize how badly I needed to return to the islands.

I went to Australia and found a job cleaning boats. It gave me the opportunity I needed to be around the water all day. Ever since then, I have been working on boats for years. At the end of the year, I saved enough to get back around the world. (A short surf trip to Costa Rica but that’s another tale.)

When I returned to O’ahu, a boat repair shop owner found me (finally, after months of communicating) and picked me up at the airport. We struck a deal.

I began cleaning boats for his repair company and learned the harbor culture. If you didn’t know, it is quite lively and vibrant once your welcomed. I saved up enough money to buy a little boat of my own, so I could stop depending on friends’ couches. I wanted my own space.

I looked at several boats, but when I saw my little Ranger I fell into a deep love with her, even her black rot and holes in the hull. I knew I could fix her back to health and begin sailing her.

My boss offered to help me tow the rotting vessel across the island and when we arrived at Sand Island, I was finally home. It took oceans of travel, nameless cities, Jobs, one time friends and that feeling of oneness you get when you’ve found the right place at the right time.

For the past two years, I’ve been living and sailing on a Ranger 23 and I would love to share the ins and outs of doing so in Honolulu as a 27 year old girl.

The Ranger, under sail, heading toward the west side.

female travel
Jessi Schultz
Jessi Schultz
Read next: Camping > Hotels
Jessi Schultz

I am mostly a gypsy but all the time a sailor, painter and lover of literature. The arts have me forever intrigued. I hope to catch your eye with my tales of the high seas and what it takes when a repair is needed and one is simply broke.

See all posts by Jessi Schultz