this post was submitted on 06 May 2026
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You could do all of this with very little money ... if you're willing to live semi-homeless near the beach. Maybe live in a van. Most expensive thing here is the wine, and wine doesn't cost that much.
I actually did this for a while. I bought a sailboat with a friend, moved onto said sailboat, and bummed around for a bit. It's cheap in bursts, but then you need things. What happens when you have a sudden need for money, like an engine breakdown or a medical emergency? What happens when you suddenly need to travel, like for a funeral or a friend's wedding?
What happens when one day you need to afford anything beyond the daily living expenditures and you need to get a job and now employees side eye you for having a year or two gap on your resume? This is possible, obviously, but it's definitely a lot more than it sounds like on the surface.
What gap? You weren't unemployed, you were a ship's captain and chief of engineering.