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Taking the initial steps....
I am reading an EXCELLENT reference right now on this subject, and recommend it highly. It is "The Crusing Life" by Jim Trefethen. What I like most about it is that it does not try to teach you how to sail, navigate, choose ground tackle, shorten sail in a storm, blah, blah, blah. All good stuff, mind you, but this book is written about the LIFESTYLE, and speaks to the questions - do I DO this, and if so, HOW?
Once you get through this book, if you are still up to the challenge, the next one to read is Beth Leonard''s "The Voyager''s Handbook." This is the first book you want to read to learn the "WHAT I need to know" before you set out on a boat and try to "wing it." I''ve seen enough bad weather on boats (without having serious blue water experience) to know there''s a whole lot of respect owed to the seas... I got caught in a serious Gale in the BVI last December, and without my boat handling skills, I could have been in some pretty serious trouble. Not tooting my own horn here, but I was VERY happy that when put to the test I didn''t have to think too much.
After you get through Beth''s book, then move on to Jimmy Cornell - "The Cruiser''s Handbook" and "World Cruising Routes." I haven''t gotten this far yet myself, but I''ve heard from more than one source that these are must-read''s in the planning stages.
Also on my reading list will be one of Lyn and Larry Pardee''s books because I think the minimalist approach is the best way to do it and I understand that''s their philosophy as well.
Hope these recommendations give you some confidence in these resources. There''s a lot to read, and if you''re like me you hate wasting your time and money on books that are all a bunch of fluff.
As for selling off your stuff... Just do it. I left a 2,700 sqf home and now live in a small, 3 br, rented house paying 1/3 the housing expense. I have 1/2 as much stuff, and am "that much closer" to the water. Let me tell you something... It feels great!