How We Made the Leap to Full Time Cruising

Before full-time cruising entered the picture, we had what many would call the perfect life on Canada’s West Coast: a sleek apartment, career success, adventurous vacations, and all the gear for expensive hobbies like mountain biking and road cycling.

We thrived in our demanding tech and real estate careers and escaped on weekends with mountain bikes and sushi. Our apartment had everything a city dweller could want—espresso machine, flat-screen TV, and a cozy designer couch.

Who would want to leave this? Us apparently.

From the outside, it looked like we had it all. But something was missing.

The Dream Begins

Just as we were preparing for a long-awaited vacation, the Covid-19 pandemic hit. Like many, we started rethinking our priorities.

A sneaky trip to Mexico introduced us to a different kind of life—one filled with digital nomads, expats, and sailors. People were living at the beach or traveling on their boats full-time.

That short trip changed everything. The idea took root: If they can do it, why can’t we?

The trip that changed it all

Making the Decision

Back in Canada, we committed to making the liveaboard lifestyle a reality. Sailing felt like the right fit—we had two dogs, so flying wasn’t ideal, and RV life felt limiting.

We kept our decision quiet at first, knowing it might be hard for our friends and family to understand. But the fire was lit.

Planning & Preparation

From our small city apartment, we worked full-time jobs by day and binge-watched sailing YouTube channels by night. These videos showed the dream—sunshine, cocktails, and anchorages in paradise.

What they didn’t show? The struggle. The transitions. The reality of going from land life to boat life.

Then we met Max, our future yacht broker, fresh off a seven-year sailing trip with his family. He was a wealth of knowledge. Of both the positives (many) and downsides (also many). We told him we were on a five-year plan. He laughed and said see you soon.

We signed up for sailing lessons—but Covid had other plans. So we did what any desperate dreamers would do: we bought a sailboat off Craigslist, with no experience.

Yes, really.

The Craigslist boat

We’d never even stepped on a sailboat. But we had one now, so back to Craigslist we went—this time, to find a willing teacher.

After some moderately successful early attempts and only one dock collision, we took a proper CANSail course, gaining real experience and confidence.

Not long after, Max found us our “perfect” boat—sturdy, refit, and in our price range. We bought her, joined the Bluewater Cruising Association, and dove headfirst into learning. I started crewing on race boats. Mark studied every system on our new home.

We weren’t just dreaming anymore—we were preparing.

Downsizing & Letting Go

We made the call: it was time to move aboard.

We sold the apartment and cleared out nearly everything. From Craigslist sales to donations, we got rid of 95% of our belongings. We stored only a handful of sentimental items with family and kept a few things to make the transition easier—some bikes, work clothes, and a few small appliances.

Move out day

At this point, people started asking questions. Most assumed we were just “trying out boat life” or “just living on a boat.” We didn’t correct them. Some friends were skeptical, so we kept it vague.

Remember that five-year plan? After two snowy winters—sometimes frozen in place on a river —we ditched it.

Thanks to savings, promotions, and the apartment sale, we were financially ready. All we had to do was quit our jobs.Surprisingly, that was the easy part. Mark turned down a remote-only offer from his company. I arranged a very part-time gig to keep my real estate licenses active. The sailing sabbatical (ha-ha sabbatical) had officially begun.

Departure Day

After all the prep, we were finally ready.

We threw a farewell party, said our goodbyes, and untied the dock lines from the city we’d called home for 15 years.

We didn’t sail far that first day—just a few hours away. But the freedom was real. We were no longer tied to land. The horizon was open, and our new life had officially begun.

It felt terrifying. It felt incredible.

We didn’t go far, but the views were worth it.

Reflections & Advice

Looking back, the hardest part of transitioning to the sailing lifestyle wasn’t learning to sail or selling our stuff—it was walking away from the version of life everyone else expected us to live.

Full-time cruising isn’t just about sunsets and sandy beaches. It’s uncomfortable, uncertain, and occasionally overwhelming. But it’s also deeply rewarding. We’ve become more resilient, more resourceful, and more present.

If you’re dreaming of a big life change—trust that dream. You don’t need all the answers. You just need to take the first step.

The day we untied the lines, we stopped living for weekends and started living for ourselves.

We weren’t expert sailors or millionaires. We just made a decision—and backed it up with action, one imperfect, brave, and sometimes stupid step at a time.

If full-time cruising is calling to you, don’t ignore it. It just might change your life.