Finding the right boat is easier said than done. For the past few days, I’ve been deep in the rabbit hole—endlessly scanning market listings, scrolling through boat brokerages, and comparing specs. The market is flooded with options, but filtering through them quickly reveals two main categories: overpriced rigs way outside a practical budget, or cheap project boats that simply aren’t worth a second glance. Finding "the one" is clearly going to take some time. But instead of letting the search stall my progress, I’ve decided to pivot my strategy: start small. Before committing to a larger,…
The most expensive mistake in boating is buying a boat before you know what you are looking at. So I am learning first.
And since I am building this site with Claude anyway, I made learning part of it: the Library. Playful lessons for everything in boating. You label a boat, tie the knots, read the wind, and now you can even tune a radio and hear what a Mayday call sounds like.
You earn points and ranks along the way, from Deckhand up to Captain. I am a Deckhand too, so we start at the same place.
If you are also dreaming of the water, join the crew. It is free, and you do not have to be perfect. You just have to start somewhere.
Looking through boat listings is a full-time job. So I asked for help.
Together with Claude, an AI assistant, I set up a "vessel scout". Its job is to go through boat offers, check them against what I want (size, condition, price, how far away), and write me a short report on what is worth a look and what is not.
A few rules I gave it: it does not contact sellers, it does not decide anything for me, and the first real search is still ahead. I look at Facebook Marketplace by hand myself.
What I like about it: it never gets tired of bad listings. I still make every decision. But I no longer have to scroll for hours to find one boat that makes sense.
I changed the plan a little. Not one boat, but two.
Boat one is a tiny starter boat. A dinghy or a small sailboat, something I can handle alone and fix myself. This is where I learn to sail, make mistakes in shallow water and earn my licence.
Boat two is the project boat. A real cruising boat that I can slowly bring back to life. But only after I know what I am doing.
This way I do not have to learn everything on a boat that can hurt me, or my wallet. Small first. Then bigger, when I have earned it.
Finding both will take time, maybe months. That is fine. The hunt is part of the story.
This project needed its own place. So it got its own name: Almost Captain. Because that is exactly what I am. Almost.
Today the pieces came together: - a YouTube channel, @Almost-Captain - an Instagram account, almost.captain - this website, almostcaptain.com
I made one rule for myself: start clean. No ads, no sponsors, no affiliate links, no money of any kind. It is a private project, and I want you to see it the way it really is. Followers and a crew first. Everything else can wait.
You are welcome to follow along on any of them. The website is where everything ends up.
For years I have watched sailing channels. The guys who actually do it. The ones who show that it can be done. And the ones who only talk about fancy things.
At some point I asked myself the simple question: what do I actually want? The honest answer is a life on the water. A boat to live on, and the freedom that comes with it.
A big, shiny yacht is not the way there. It costs too much, and I would be the captain of something I do not understand. So the dream got smaller, and that made it better: one project, one boat I can afford, learn on and fix myself.
I am not 20 anymore. I want to do this properly, step by step, without breaking the bank. This is where it starts.