Go now. Don't wait to build your kitty for another 3 years, especialy if you have a gf that is game to join you.
Well, there is the technicality of getting a boat first...that takes SOME saving
Though she's quite open to the idea, and loves to travel (spent her junior year of college in Moscow), she's actually never been on a sailboat before, and wants to make sure she likes it before diving in all the way. Since we live quite a ways from the water right now, the general plan is to move back to the Baltimore/Washington area next year and get some experience on my Dad's 25-foot friendship sloop while continuing to save.
When the kitty and our sailing skills are a bit more mature, we would then take off...in our own boat. Dad built "Amnesty" together from planks, and I doubt he'd just let us go bouncing off in her. Besides, she's not much of a blue-water boat, from what he tells me.
In the meantime, though, I fantasize about the life by putting "Old Bay" on EVERYTHING.