Which boat do you really want?
Y'know, I think that question, when we're talking about the last boat, the post-retirement crusing boat, almost deserves it's own thread.
IMO it is the question that should be asked last.
First question: how much ready cash will you have when you retire?
Second question: how much monthly income will your investments/IRAs, etc., bring you?
Third question: Are you going to cruise for a fixed length and return to the dirt by choice, or are you going to adopt the "no fixed address" lifestyle for good?
Then ask, "Which boat do you really want?" shortly after asking "how much can i really afford?"
We've all seen folks who waste months kicking tires on boats that everybody but them knows they cant afford until they finally accept the reality that they need to look in the $50K range, not the $150 K range. That is time they won't ever get back.