I have a 31' sailboat ready to go as my ultimate escape "just in case" I can't stay hunkered down at home. She is fiberglass, shallow draft, and rigged for all safety and comfort for the two of us. I would suggest courses from Power Squadron, USCG, and lots of reading. I learned the basics of sailing, knots, dead reckoning navigation, rules of the road, and lots more from those courses, but the best teacher was experience...in little baby steps. We sailed in bays, then marina-hopped on the Texas coast, then headed out to blue water when we felt confident. Of course, have a VHF radio, GPS, Epirb, and all the goodies...harness, tether, life jackets. Welcome to the world of those of us who like to throw money into a hole in the water!