My dream is to retire on a sailboat in the Caribbean. It started with day dreaming about winning the lottery, and "what would I do if I won". The as I got older, I started thinking "I can do this". Then I started doing research on the subject and what it would take to make it happen. Some of my early concerns:
Having this in the back of my mind for years, as a common daydream, I really started looking hard, and was surprised at some of the answers I found.
I took some basic sailing lessons at Tempe town lake. Not much use, but some of the basics. I read quite a bit from people that have done this, what it cost, the down sides, etc. I have also signed up to take a week long sailing lesson in St Vincent and the Grenadines, where I will spend a week in the southern carribean, living on and learning to sail a catamaran similar to what I want to purchase.