Why I sail, by Stefano
There’s nothing inherently special about sailing. It just happens to be one of the many very cool things humans can do.
But when I ran my personal “how to live a life” question through the optimiser, feeding it my requirements for efficiency, independence, self-reliance, long-term viability, adventure, and the ability to explore the world, the algorithm spit out a single answer: living aboard and cruising on a small sailing boat.
Let’s examine the other candidates.
A traditional home? It fails almost every requirement, except for being long-term and comfortable. Comfort is nice, but it tends to remove the very friction that makes things interesting.
An off-grid cabin in the wilderness? It ticks most of the boxes, but exploration becomes a separate logistical problem. Not very efficient in that sense.
Backpacking? Amazingly minimalistic, but not truly sustainable for decades. (Though sometimes I do wonder…)
A campervan? This is sailing’s closest competitor. But van life usually means highways, campsites and parking lots. With a boat, you gain access to a far greater number of stunning, remote places; places that simply don’t exist on land in the same way.
There’s also a timing issue. I can do van life later, when my back starts complaining. Sailing is harder on the body. It demands more of you physically. It’s a now-or-may-regret-it-later situation.
And sailing does more for me than just moving me around. It forces me to learn: navigation, aero- and hydrodynamics, weather, geopolitics, survival, environmental awareness, teamwork, patience, and surrender to the power of nature.
A sailing boat can circumnavigate the planet powered almost entirely by wind and sun.
To me, sailing represents the last meaningful piece of freedom left in our society. Maybe one day we won't be able to sail across oceans anymore because private owners have robbed us of this shared resource, as they've done already with most of our land. Until someone invents an efficient personal spacecraft, sailing feels like as much freedom to wander as we’re going to get.
There’s probably some romantic nonsense mixed in, too. The seafaring stories I heard as a kid. The (absurd cultural) admiration for pirates who were, let's be clear, dirty criminals, but fascinating ones. Maybe a bit of that infected me.
And then there’s something I can’t quite explain, but the world looks more beautiful from the water.
I live on a sailing boat because for me, it’s the most efficient and interesting way of living I can think of.
Stefano, Feb 10th, 2026
