Please tell me it is worth it???
Lots of good advice so far.
We did what you are doing in 1995 and in 2001. We were about 150 miles from the coast and it was difficult to not be thought of as nuts. Don''t let weak jealous people crush your dream. They envy you, whether they know it or not, and to see you do this shows them how hollow their lives will be compared to yours. People want you to fail so they can say, "see, we couldn''t do that, it''s impossible".
Commitment is the key. There will be good days and bad days, but don''t let a day go by without dreaming. Think of the boat in your mind, the islands, the people you''ll meet. If you both want it bad enough, it will happen.
We sold a 3000 sq ft house and in one day moved aboard a 30 foot boat. We''d had the mother of all garage sales, sold the cars, everything. My wife and I both thought selling nearly everything was the most freeing experience of our life.
You''re lucky if your son wants to go too. We left with a 9 yr old girl and 6 yr old boy. Both wanted to go even though they knew most of their possessions weren''t going with them. Part of the reason was that my wife and I were enthusiastic about it (sometimes only for their benefit). Another was that we were already homeschooling. There was not as big a transition for the kids. We also killed our TV and and focused on what we wanted, not what tv wanted us to have.
When you are old, either you will say that you nearly left on a sailboat to Tahiti and regret not doing it, or you will say that it was the greatest thing you ever did. You may not be in as nice of a retirement home because of it, but my philosophy is that I''m going to retire with more memories than money.
Get some cruising books (esp Sensible Cruising), subscribe to magazines and talk to people who have the same interests. You may be surprised, in Central Washington there were a few people who shared the dream.
Stay focused and keep in touch.