I'll second Cap'n Pollard.
People manage to cruise the world after decades of hard work and years of preparation. But it ain't easy, and frankly there's something about the tone of your post that sounds a bit pipe-dreamish to me... Somebody on this forum once said "You have to EARN the right to cruise." My sense is that you might think the process is easier to do than it really is, that things will naturally fall into place and one day you'll wake up in paradise with a boat in the backyard. I've had the same dream, and in five years I've made it from northwest Colorado to Hilton Head Island with a 28-year-old Catalina 30 parked twelve minutes away by bicycle. Ain't the South Seas, and it isn't a big boat... but it's a move in the right direction.