How We Keep Cruising: Making Money at Sea

Yes, You Can Make It Work

When we tell people we live full-time on a sailboat in the tropics, most assume we’re either retired or sitting on a hefty trust fund. Truth? We’re neither. We’re just two regular people who decided that time was more valuable than stuff—and figured out how to make money sailing so we could keep doing what we love.

Surprisingly, most younger cruisers we meet are still working. Just… not in the traditional sense. Same goes for us.

This isn’t a “Top 10 Side Hustles for Cruisers” list. It’s a look at our real experience with making money at sea, how we afford cruising, and what we’ve learned along the way.

What We Did Before (and Why We Left It Behind)

Before boat life, we both had stable, well-paying careers. Mark worked his way up from an IT technician to managing large tech teams in industries like hospitality, real estate, and mining. I worked in real estate—specifically strata management—for over 15 years, eventually earning my Managing Broker license.

We were doing well financially, living in Vancouver. But over time, our priorities shifted. We started to value our time more than our paychecks. That shift in mindset led us to sell it all and chase a different kind of life at sea. (You can read more about that leap [here].)

Honestly, quitting the 9–5 should have been scarier. But we had savings to float us for a couple of years and figured we’d deal with the money part later—either pausing boat life to work or figuring out how to work while sailing.

What We Do Now: Remote Work on a Boat

For the first year, we took a break from work entirely and lived like retirees—no deadlines, no meetings, just maintenance and margaritas.

No meetings here.

But eventually, real life caught up. Here’s how we’re currently keeping the bank account above zero.

Jaclyn: Freelance Writing & Content Creation

Freelancing wasn’t the plan when we left. I actually kept my real estate job at 2 hours a week, just enough to pay the Starlink bill. When my license expired, that ended—and, thankfully, writing work started to grow.

Thanks to a referral from a friend, I picked up a couple of freelance content writing clients. Word spread, and soon I had a small roster of real estate and lifestyle clients. Real estate is my niche (because of my background), but travel and lifestyle writing requires more effort—more research, more pitching, and more hustle.

I’d love to say I spend my days writing from the bow with the sea breeze in my hair. In reality, I’m below deck, sweating in front of a fan, writing about bylaws and condos while everyone else is out surfing. It’s not glamorous, but it works.

Mark: Freelance IT & Crypto Enthusiast

Anyone who’s talked to Mark for more than ten minutes knows he’s had success with cryptocurrency and is a Bitcoin enthusiast. In fact, crypto helped us afford the boat. We were lucky to sell off most of our Ethereum(ETH) near it’s peak in 2021. While it’s a small part of our income, it’s part of a long-term investment strategy that he keeps a close eye on.

Most mornings, you’ll find Mark watching the markets. When it’s good, it’s really good. When it’s bad, we lean on our other income streams.

Mark also fell into some IT consulting contracts through friends we met cruising. He helps companies with everything from security compliance to long-term technology roadmaps. Since his previous roles were project-based, switching to freelance wasn’t a huge leap—though managing multiple clients remotely does take some extra effort.

How We Set Ourselves Up for Success

We didn’t set out planning to work right away. We wanted some time away from our previous careers to figure out how we actually wanted to spend our days. We didn’t over-plan or map out our next steps - we just knew we needed a break and trusted we’d figure the rest out as we went.

Thankfully, we already had the tools we needed onboard—Starlink, good laptops, and reliable phones. We also had enough savings to not worry about work in the early days, which gave us the space to figure things out.

We agreed on a financial “hard stop”—a number in our bank account that would mean putting the boat in storage and going back to full-time work. So far, we haven’t hit it. Between Mark’s trading and consulting contracts and my mix of short-term freelance projects, we’ve been able to stay afloat. We rarely touch our investments, treating them more like a rainy-day fund.

Other Income Ideas We’ve Considered

We’ve toyed with other ideas to avoid going back to land life.

Like many cruisers, we briefly considered YouTube. But the return on investment just wasn’t there for us—it’s a ton of work for very little financial payoff unless you really commit.

Instead, we started a website to keep family in the loop, which has slowly grown into something bigger. The ad revenue is small (think: a beer or two a month), but it helps.

We’re also constantly looking at ways to diversify—without having to sell feet pics. (We’re not there. Yet.)

Challenges and Lessons Learned

Working from a sailboat is not a YouTube fairytale. We’ve had to adapt, problem-solve, and laugh through the frustrations.

Workspace Woes: Our 1970s boat wasn’t built with remote work in mind. We bounce between a retrofitted nav station, the cockpit, and the salon—none of which are particularly ergonomic. Add tropical heat, and you’ve got a sweaty, sometimes cranky freelancer situation.

Sometimes working means sharing spaces.

Time Zones: As we sail south and east, time zones get tricky—especially since most of our clients are on the West Coast. There have been more than a few times I’ve shown up to a call an hour early (or late).

Work vs. Play: During busy cruising seasons, carving out focused work time can be tough. There are potlucks, surf sessions, and endless reasons to close the laptop. But deadlines don’t disappear. We’ve had to learn how to say no to the fun sometimes, even if it’s hard.

Why It Works (For Now)

It’s not all doom and gloom, though. In fact, this flexible work lifestyle is exactly why we started cruising.

We don’t have weekends in the traditional sense. We might work a few hours in the morning after a surf session, meet friends for happy hour, then pick up another project later in the evening. Working through the weekend just means taking time off mid-week—when the anchorages are quiet and the tourist spots are empty.

This life gives us freedom. We’re not tied to a desk, and we’re not stuck in one place. Freelancing gives us the ability to travel, explore, and still keep our finances afloat.

Would we like more financial stability? Sure. But for now, it’s working.

And if it stops working? We’ll adapt—hopefully before we have to resort to selling feet pics.

Not that desperate yet.