this post was submitted on 17 Jul 2026
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I know it should set off alarms when there are always sailboats for sale relatively cheap but I struggle to resist the urge to buy a cabin sailboat I can sleep in. In my imagination it'll be like an RV but in the Gulf.
To simulate sailboat ownership, turn your shower on maximum cold, stand directly under the faucet, and tear $100 bills into pieces.
(Not my joke)
That is a funny joke and I've heard others like it but I guess I just don't know enough about boats to understand why it'd be so terrible.
A fiberglass shell with an outboard is like a Costco chef's knife, it does the job and you basically just need to clean it and whet it to keep it at around 90% performance, with very occasional sharpening. Cutting tomatoes kinda sucks.
A sailboat is like owning a single-faced Japanese watered steel knife. You better clean that thing and dry it and oil it every time. You have to either learn a very very delicate time consuming process to keep it in shape that you do every month, or you have to take it to a specialist who will charge you your hat and ass. It's far harder to correctly operate if you want to get the results you see on tv.
And, if you try it once and you know you've fallen in love with sailing for the rest of your life, go volunteer at a local sailing club. Maybe get a small fiberglass catamaran with a sail.
Under no circumstances should you get a wooden sailboat unless you are floor-ckreakingly rich, or it is your lifestyle.