[camaraderie]

While I don't agree with the whole teenager thing, I do think it is both possible and important to plan ahead and have specific goals along the way rather than some vague notion of leaving in 11 years. We dreamed of sailing away for 30 years...but had a firm plan 15 years out that (if achieved) would allow us to cruise comfortably and meet our family obligations and be competent at sea. Things to consider:
1. Kids college education fund
2. Nest egg required to allow cruising budget
3. Learning to sail in increasingly more difficult situation...both parents.
4. Navigation/Weather and systems repair skill building
5. Initial cruising plans and data gathering required
5. Buying the right boat and deciding how to outfit.
6. Downsizing and making arrangements to live on the move (mail, banking etc.)

Each of these points (and more) require a plan and some goals along the way and adjustments. There will be setbacks and surprises but without such planning, the likelihood of ever being able to leave AND be safe AND sustain the cruising lifestyle goes way down.

Example: It will be 16 year until your son attends college. Public University annual costs average $13K today. In 16 years we can reasonable expect that cost to be $30K or $120K for 4 years at the LEAST expensive type of college. How will this be funded. Lots of possible answers including..."if he wants to go he will find a way" and "he can join the army and get educated there" and "we need to set aside $10k per year for the next 11 years in order to fund his education" . Point is...a plan is needed. You are right to start putting one in place now if you ever hope to go.