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.

There are a lot of annoying things needed that aren't accounted for......like heating and running water and waste drainage. But if you're willing to get creative then anything is possible.

I know people who have done the ski bum/beach bum thing at various phases of their life (probably most fun between the ages of 20-30): get seasonal jobs in tourist areas where the job gets you subsidized employee housing and free passes to something like a ski mountain, use the local favor economy to give and get free or heavily discounted stuff, and just have fun.

Eating well is definitely the most expensive thing.

You live in a van on the beach, just bulk buy grape juice and leave it outside for a few years.

Yeah I think the problem is that to have any money you'd still need a job. The core fantasy with all these things seems to always come down to having no job or very little hours at a job. But I agree this could probably be fine for $20,000/yr in most places. Still would need like 400k+ to retire that way depending on age, but that's a realistic amount for a good amount of people at least... The hardest part is having the good friends around tbh. You pretty much have to get lucky with finding cool people near your same beach.