The 5 biggest fears of living aboard a sailboat (and what really happened)

When we first decided to cut the dock lines, we were equal parts excited and terrified. Selling everything, moving aboard full-time, and leaving behind stable careers was not a small decision. Friends and family asked if we had lost our minds, and many of their questions reflected the very fears that were already swirling in our heads.

Before we left, we carried five big worries about the cruising lifestyle. Would we run out of money? Would we die at sea? Would we feel lonely? Would the boat constantly break? Would we regret the decision altogether? Now, after years of sailing full-time, here’s the reality behind those fears.

Fear #1: Running out of money while cruising

Even though we worked hard at preparing, we feared that living aboard a sailboat would drain our savings fast. The fear of being a poor boat bum was real. We had good jobs, sold all of our belongings, and lived aboard in the marina for a couple of years to save even more. We figured we had enough to fund a couple of years (max) of sailing without draining all of our money.

Selling and leaving the apartment was more traumatic for some than others.

What actually happened

The first year, our biggest mistake was treating cruising like a vacation. We spent freely on dinners out, clothes, and every activity that crossed our path. By year two, the fear of burning through our funds forced us to rethink our spending.

We adjusted by:

• Tracking expenses closely.

• Cutting back on “vacation mode.”

• Finding new income streams through content writing, IT consulting, investments, and even some day-trading.

Working isn’t everyone’s favourite, but it’s extending the cruising.

What we learned

Originally, we were convinced that running out of money would send us back to land life. Instead, adapting helped us extend what was supposed to be a one-to-two-year adventure into multiple years, with no end in sight.

Related: Cruising Budget: Our Real Costs of Living Aboard

Fear #2: Dying at sea or facing real danger

This one is mostly my fear, and honestly, it still lingers. I’d sit in the cockpit at night imagining worst-case scenarios: pitchpoling, knockdowns, waterspouts, even hitting a whale.

Calm and peaceful, but mentally I’m going through ways to die at sea.

What actually happened

So, is sailing dangerous? Yes, but no more so than driving a car or crossing a busy street. We’ve had rough passages down the U.S. West Coast, weathered a few storms at anchor, and dealt with conditions that kept us on our toes. But we survived, and we’ve learned.

Our safety practices include:

• Wearing lifejackets (always at night and in rough seas).

• Tethering into the cockpit or jacklines.

• Choosing conservative weather windows.

• Carrying redundancies like a liferaft, dinghy, safety gear, and insurance.

What we learned

Fear is still there, especially on dark overnight passages, but experience has made it easier to manage. The reality of full-time cruising is that safety is about preparation, not panic. As best we can, we managed the situation.

Related: Cruising 101: Must-Have Gear We Actually Use on Board

Fear #3: Not making friends or feeling lonely

Before we left, we worried about losing community. Our land life revolved around mountain biking and the friendships that came with it. Once we stopped biking, we already felt friendships fading. Sailing away only amplified that fear.

What actually happened

At first, it felt justified. Along the coast of British Columbia, boats kept to themselves. But by the time we reached San Francisco, everything changed. We discovered that making friends while cruising is often as simple as paddling over to a neighboring boat and asking about a bonfire, spearfishing trip, or some surfing.

Over time, some of these friendships have felt like family. Cruisers help each other out. When Mark flew back to Canada, I had people offering to sail with me, fix things, and drop off fresh food.

Life’s pretty social these days.

What we learned

The downside? Goodbyes. Friends scatter to new destinations or even back to land life. But the upside is having a global community that makes the world feel smaller and friendlier.

Fear #4: Constant boat breakdowns and maintenance

YouTube loves to say, “Cruising is just fixing your boat in exotic places.” We braced for constant breakdowns and expected non-stop headaches.

What actually happened

Reality? Things break, but it hasn’t been the endless nightmare we feared. Yes, we’ve had issues—like a failed seacock, a dead dinghy, and even a lightning strike—but they’re balanced by stretches of smooth sailing.

What we learned

What keeps it manageable:

• Regular haul-outs.

• Preventive maintenance schedules.

• Budgeting time and energy for repairs.

Compared to land life, it feels about the same: ongoing projects, occasional emergencies, and plenty of problem-solving.

There’s still work, but it’s not all that bad.

Related: Cruising on a shoestring

Fear #5: Regretting the decision to sail away

What if we hated it? That was the scariest question of all. We had sold our apartment, given up promising careers, and traded stability for the unknown. Sailing under the Burrard Bridge in Vancouver, we both silently wondered if we’d made the biggest mistake of our lives.

What actually happened

Regret still creeps in on hard days, like lightning strikes, but the balance tips when we see whales breaching, turtles swimming past, or sunsets that rival paintings.

What we learned

When people ask if we regret it, our answer is no. The worst-case scenario is simply going back to land life and jobs, which is the “normal” path we left behind. The cruising lifestyle has challenges, but it also gave us more than we imagined.

A good day surfing cures all.

What we learned about fear and sailing life

Looking back, we realized that most of our full-time cruising fears never came true in the way we imagined. Money fears pushed us to find creative income. Safety fears taught us to prepare, not panic. Loneliness fears gave way to a strong community. Maintenance fears turned out to be manageable. And regret? Not even close.

The reality of living aboard a sailboat is that fear never disappears—it just gets quieter with experience. Sailing full-time is not without challenges, but it is a life worth choosing.