We’re Steph and Travis from Sailing Jibsea, just a couple of noobs that didn’t know much about sailing, who took off from Canada during a global pandemic with very little sailing experience.

We are full-time liveaboard cruisers currently exploring the Caribbean on our 1990 Hunter 42 Passage. We have been living on the big blue since we left our home port in Port Credit, Ontario in the fall of 2019. In our first year of cruising, we made it from Ontario, Canada to Grenada where we spent hurricane season and have shared our journey via vlogs on our YouTube Channel (Sailing Jibsea) and our social media accounts (Instagram @sailingjibsea, Facebook: Sailing Jibsea). 

The first question we often get asked is “What made you guys decide to do this?”

No great stories start with logic, this is how I (Travis) have lived most of my life! So when people ask us how we started cruising, we usually get a get a good laugh while telling the tale.

“Somehow found myself looking at sailboats”

It was winter 2017 and I was searching the web for used kayaks, looking forward to kayaking over the summer months up in northern Ontario, the province of endless lakes. I fell down the wormhole as one posting led to another and then somehow found myself looking at sailboats and reminiscing in an old dream I had of sailing the world (laughing silently to myself thinking you need to be rich and extremely intelligent to sail). Amongst the beautiful sailboats I was daydreaming about, a small and old 1978 Chrysler 22 with sleek lines caught my eye, with a price I couldn’t refuse. The very next day, I drove three hours from Mississauga to Kingston, Ontario, in the snow, to buy a sailboat I knew nothing about. The sense of adventure took control and I was just along for the ride.

It was a trailerable sailboat with a swing keel and rudder, a hoisting mast and a little outboard. With the masts, rigging, sheets and halyards laying all over the decks. I had no idea what I was looking at or even what questions I should ask. I just knew I was too excited to care. I asked the only question I could think of at the moment … “Does it float?” “Yes!” the owner replied. “Perfect!” I responded, as I handed the owner the cash. As I was about to hook the trailer and the boat up to my truck, I walk around the trailer and notice that all the tires are flat and the trailer had no lights. I quickly jet off to closest Canadian Tire to find some trailer lights and sort out the tires. I get everything in order before the early winter darkness sets in. Now it’s time to start the three hour drive home in the snowy dark!

At the time, Steph and I were just starting to date and she messaged me that evening asking what I was up to. I told her that what I had just purchased and I’m pretty sure she thought I was crazy. To her knowledge, I was only in the market for a kayak, but I think she was secretly as excited as I was.

“I meant to buy a kayak but ended up with a sailboat that changed our lives”

Now at this point, Steph and I had no plans on selling everything and sailing away, what every sailor dreams of. Over the next few winter months, I spent a lot of time staring at the boat and googling what things were and what they did. I painted the interior bulkheads and trim making it as clean and aesthetically pleasing as I could in hopes Steph would join me in some sailing adventures in the upcoming summer months.

The long Ontario winter is coming to an end and with a whole lot head scratching trying to figuring out how to set the mast up, I was feeling confident enough to take it out on the lake to test its ability to float. Steph and I get it in the water just shy of a boat launch fail video.

“Yay, The boat floats!” We look at each other in utter confusion, unsure whether we felt safe or not. We swallow the fear and I start the outboard and with a cloud of white smoke, we set off the dock for the most comical first sails I’m sure anyone could have ever witnessed.

No wind, depth, speed, or navigation instruments of any sort, not even a flag to show us where the wind was coming from. The cloud of smoke from our old two stroke outboard showed us which way the wind was coming from. We get past the safe harbour break wall and turn off the motor. Suddenly, we were going overcome by peacefulness and beauty…until we tried to set up the sails up. I held the jib sheet in one hand, the main sheet in the other while trying to steer with one foot on the tiller. Sails and sheets were flapping everywhere. I remember looking at Steph laughing and telling her “I don’t think I’m doing it right.” “I thought you googled how to do this, are we going to die?” All I could respond with was, “Can everybody just give me a minute?!” as I chuckled with how ridiculous I must have looked trying to maneuver the small, yet what felt like at the time, massive sailboat.

That day, I learned what it takes to become a good sailor. You need to be able to control your stress level in order to think clearly in whatever the circumstance. As we drifted further off shore on our lovely (and hilarious) sunset sail, we decided to drop the flapping sails and motor back to safety before it got too dark. I realized I needed to read a little more on how to sail.

Summer was my busiest time for work and it took a while to set up and take down the mast, the sails and to put everything away. I had difficulty finding time during the week. My weekends were spent BMXing, so we decided that the next time we’d take the boat out would be for a long weekend up in Tobermory, Ontario on Lake Huron.

We took the sailboat up to Tobermory twice that summer and both times learned a little more how to sail but we mostly motored. Now that I know more about weather forecasting, I can’t believe what we got away with and how lucky we were in going where we went with no weather forecasting, VHF, navigational instruments or really much of anything. At the same time, it felt very ‘Christopher Columbus’ having nothing but our senses.

The next winter is when I found myself spending countless hours online. I spent all my free time reading and watching anything related to sailing. That’s when I came across various young sailors on YouTube, making it seem possible for us to go for that dream.

Steph and I playfully tossed the idea or buying a bigger sailboat and sailing off to travel the world. Steph was on a bit of a different path with her golden handcuff career and I was building a company. For me, life is more about living for the adventure than it is to be living for the money. One day, I realized I was going to give it my all to bring this wild dream to fruition. Steph expressed that she was ready for a change in her life and was ready for a big adventure. In 2018 we decided to turn the dream into a goal. Once we set a date on our goal, it become our reality and there was a drive instilled in us like no other. We changed many aspects in our day to day living from no longer dining out, going to different grocery stores to get cheaper prices, price matching and selling possessions that were no longer of value to us. We lived very frugally, spent only what were necessities and banking the rest knowing we had a certain period of time before our departure date.

Next month, I’ll go into how we unexpectedly find Jibsea, why we chose her for our adventure and as our floating home.