By Diona Young
Table of contents
I got my first passport in 2013, around the age of 25.
Not because I had dreams of international travel. Not because I had plans to sail around the world. In fact, I wasn’t even much of a sailor.
The reason I got a passport was simple: my mom had moved to a Caribbean island, and I wanted to visit her.
Growing up, my family didn’t travel internationally or even by plane. We were a family of five on a modest budget. Our vacations usually meant packing into a van and driving five or six hours to our destination. Flying wasn’t something we did, and sailing certainly wasn’t on my radar.
That changed after my parents divorced.
Like many people starting a new chapter, my mom began looking for hobbies and experiences she had always wanted to try. When she discovered sailing, she quickly fell in love with it.
Around the same time, she met Chris, who had spent much of his life sailing and owned a sailboat of his own. What began as a shared interest eventually grew into something much bigger. When an opportunity came up for Chris to start a sailing school in Grenada, they couldn’t pass it up.
So, in 2013, I got my very first passport and headed to Grenada.
Why I thought sailing was not for me
At the time, I had only been on a sailboat once when I was 18. It felt very unstable, and it made me very nervous. I didn’t enjoy it much and thought sailing was not for me.
It was something other people did. It wasn’t a hobby I was interested in pursuing, and I certainly didn’t expect it to become a significant part of my life.
On my first visit to Grenada, there was a catamaran sailing course with only two students onboard. My mom suggested I spend a day aboard to see if I would enjoy it more than my first sailing experience.
I agreed mostly because she asked, but if I’m being honest, I wasn’t going into it with a positive attitude.
I wasn’t looking for a new hobby. I wasn’t searching for a new career. I wasn’t trying to reinvent myself.
I simply said yes to spending a day on a boat to support my parents’ love of sailing.
A day aboard a catamaran changed the rest of my life
The funny thing about life is that sometimes the moments that change everything don’t feel particularly important when they’re happening.
When I stepped aboard that catamaran, I knew this experience was different from my last sailing experience.
The boat felt comfortable and welcoming. The atmosphere onboard was relaxed. The students were learning, asking questions, and having fun. Instead of feeling intimidated, I found myself enjoying every minute of it.
What started as a day sail turned into a two-day trip to Carriacou with the class and my mom.
Somewhere between Grenada and Carriacou, something shifted.
I discovered that sailing wasn’t what I thought it was.
It wasn’t reserved for experts. It wasn’t a club that required years of experience before you could participate. It wasn’t something you had to grow up around to enjoy.
It was simply an incredible way to experience the world.
How sailing became my portal to the world
At the time, I thought I had just enjoyed a fun couple of days spending time with my parents and trying to understand this lifestyle.
Looking back, I realize I had taken the first step into a completely new chapter of my life.
The older I get, the more I appreciate what my parents really gave me.
They opened a door I didn’t know was there.
Before that trip, I didn’t know it could be an incredible way to travel. I didn’t know it could connect you with people from all over the world or take you to places most travelers never see.
Most of all, I didn’t know it was something I could do.
Oh, the places you’ll go
Over the years, I continued sailing and eventually completed my certifications through ASA 114. I’ve had opportunities to visit ancient Greek ruins, have dinner in a treehouse, play with pigs that live on an island, and, most importantly, bring my friends and family along on amazing sailing journeys.
What started as a visit to see my mom became one of the most meaningful parts of my life.
None of it was planned.
None of it was part of some long-term goal.
It all began because someone I trusted encouraged me to give something new a try.
Today, I help run my parents’ sailing school and enroll students in our courses.
Every day, I speak with people who are curious about sailing but aren’t quite sure if it’s for them.
I understand exactly how they feel.
Truths and myths about becoming a sailor
Many of them think they need experience before they begin.
They worry they’ll be the least knowledgeable person onboard.
They assume everyone else has been sailing for years.
The reality is that most sailors start exactly where they are: curious, interested, and a little uncertain.
Many of the students I talk with remind me of myself before that first trip to Grenada. They aren’t looking to become sailors. They’re simply looking for a new experience.
What they often discover is much bigger than they expected.
If you’ve ever found yourself curious about sailing, consider this your invitation.
You don’t need a sailing background.
You don’t need a family boat.
You don’t need years of experience or extensive knowledge before you begin.
You just need a reason.
Finding your reason
Maybe you’re looking for a new adventure. Maybe you want to travel differently. Maybe you’re searching for a challenge, a new community, or simply an excuse to spend more time on the water.
Start there.
Ask yourself why.
Why does sailing interest you?
Why does the idea keep showing up?
Why not this summer?
You don’t need to have the entire journey mapped out before taking the first step.
I certainly didn’t.
You never know what opportunities might be waiting on the other side of yours.
About the Author
Diona Young took her ASA 101 in Grenada with LTD Sailing in 2024. Since then, she has earned her ASA 103, 104, 111, and 114 certifications and continued to build real experience on the water. She has bareboat chartered in destinations around the world, including Greece, Sicily, Tahiti, Belize, and beyond. When she’s not sailing, Diona works in sailing education and community, helping other sailors find their own confident first step onto the water.
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