Just getting webbing between my toes

Hey everybody,

Whoever out there is a seasoned vet of the seas, your opinion is greatly appreciated and needed. I am 26 years old and believe that I need to get started now if I want to get in a boat and live the dream by 35. I really want to get a sailboat and be able to cruise from one place to another and pick up odd jobs here and there. I am a seasoned veteran of the service industry and believe I will be able to find jobs no matter where I go. I am looking to get my feet wet and help out anyone on there boat locally or close by, free of charge to help get a sense of what I need to get into if I am to follow my dream. So any advice about boat size, type and anything that could help me out would be greatly appreciated. Some pertinent info would be that by five years from now, I want to have a boat that would house my wife and myself. By four years from then I want to be on our boat in FL, at least, and beginning our journey. We don't need a lot of frills, the bare minimum so any help, please throw my way. Thanks everybody the first leap of faith is usually a blind one and i am throwing my head around like stevie!