I'm in my early 50's - don't know if that is old or young. Maybe I'm a "tweener"? Both of us were research scientists at the very frontier of the field, so you cannot reenter that after leaving because one quickly becomes many years behind the curve - no way to catch back up.
We did use our house equity - sold it right before the housing crash. In the past 5-6yrs since we sold, that house's market value is still much lower than we sold it for. Our boat is insured for a total loss that would compensate us fully for it.
Everything else was also sold and we live off the proceeds as well as the savings/investments we squirreled away while we worked and made our plans.
On the other hand, like you imply here and Larry states later, cruising is definitely not for everyone. I don't think it is for many people at all, and we are rare and maybe a bit touched in the head. The VAST majority of people we meet who have retired, sold stuff, bought a boat and took off for that romantic adventuresome cruising life actually hate it. You can see it in their eyes and the way they are always jumping about looking for something to do.
It is very important to know what you like and not be fooled by some vague idea of an undefined "something else". For us, this is the life. You and Larry sound like you have yourselves figured out well also.
Mark