I mean save up a big bunch of
money or go for a big business idea and do all you can to make sure it pans out. I guess that's what I've been doing. I wouldn't say its the very best way, but developing the sailing skills takes time anyway. There is a reason that even the most basic US coast guard captains lic requires 360 days on the
water.
The whole thing can be done for a lot less money than expected as well . Generally, there are lots of ways to econimize that don't hurt too bad, like
anchoring instead of paying for marina space, you just have to find them. Also, I think someone here said it before, but there are a lot of
fiberglass boats from the 70s. supply and demand makes them
cheap. My first real sailboat cost $1200, 25 foot. My next, the one I own now, cost $4000, 27 foot. Don't think you'd want to take them
offshore, but I feel like it takes some real
learning even to get to that confidence level (for me at least). Weeklong coastal trips with a total crew of 4 or 5 are fine though and lots of fun... That's a start. Learn the skills, save some money while you do this. If you can get a passive
income from some rental property or arrange a
remote work setup in the meantime, even better. People have different ways of doing things, but one way is to get a boat now and start chipping away towards the dream.