Eight Years Afloat: What Living Aboard a Sailboat Really Teaches You
Back in 2018 I Thru-Hiked the Appalachian Trail (2,200 miles over 172 days). So when that ended, I went looking for the next great challenge. That’s when I discovered you could actually live on a boat. I hadn’t known it was even possible before. But once the idea lodged in my head, it stuck. I went on a vision quest, found a boat, consumed every book and video I could get my hands on, and stepped into the liveaboard lifestyle. I stayed there for eight years.
It was, without question, one of the hardest and most rewarding choices I’ve ever made.
Downsizing and Priorities
When you live aboard, priorities change fast. Boats come in all shapes and sizes, but compared to a house or apartment, storage is always scarce. If you try to bring your old life with you—every appliance, every box of stuff—you’ll sink under the weight. You learn to downsize. You strip things down to what matters.
Daily life changes, too. People used to ask me what I missed the most. The answer wasn’t TV, or a big bed, or even space. It was a dishwasher. Washing every dish by hand is a chore that makes you appreciate the conveniences of land life in a whole new way.
And the weather becomes part of your routine in a way most people never experience. Winters weren’t bad—I had a heater. Summers, though, without air conditioning, were brutal. Living aboard makes you live with the elements, not separate from them. Time slows down on the dock, and your mind starts to wander.
The Cost of Freedom
Boating is expensive. Repairs are expensive. And every boat is different enough that professionals seem to charge a premium for even basic work. You either need a pile of cash—or you need to learn.
I chose to learn. Living aboard turned me into a forever DIYer. You read forums. You hunt for obscure advice. You try, you fail, you fix. It’s frustrating, but it’s also empowering. Unlike living in a house—where most people just call a repairman—on a boat, you’re often your own last line of defense. That builds a kind of resilience and problem-solving instinct you don’t get anywhere else.
The Liveaboard Community
Every marina has its liveaboards, and it’s always a mixed crowd. You’ll see the ultra-wealthy tied up next to someone barely scraping by, and yet both share the same bond: a love of boats and a desire for freedom.
The community is tight-knit. People help each other out. But it also attracts a certain fringe element—the modern-day pirate mentality. Some people see living aboard as being beyond rules, beyond accountability. Freedom to a fault.
And relationships? They get tested hard. I’ve seen countless couples move aboard, only to split up. Usually one partner dreamed the dream and the other just went along. Living aboard magnifies every tension, and if you’re not aligned from the start, the boat will expose it.
The Biggest Problem: Not Using the Boat
Here’s the sad reality: a lot of liveaboards never actually use their boats. They buy into the dream, tie up at a marina, and then the fear sets in. Fear of docking, fear of weather, fear of not knowing enough. The boat becomes a floating apartment. Dreams fade.
That’s why education matters so much. Confidence is what keeps the dream alive. Without it, you just end up paying rent for a fiberglass condo that doesn’t move.
What It Really Gave Me
For me, though, those eight years were transformative. I learned sunsets never get old. I learned that traveling by boat gives you access to coastal towns and anchorages in a way no other lifestyle can. I learned that constant problem-solving keeps your mind sharp.
It wasn’t all rainbows and quite often it was uncomfortable. But it shaped how I see the world, what freedom means, and what life is really about.
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