I believe what you are talking about is more about "character building" than "learning how to sail".
The time I spent aboard the Endeavour Replica showed me less about "character" than most other places I have been. Most aboard were more concerned about their "trendy, political correct, I'm tough and cool" image than anything else.
If you really want to learn about "character", read Alan Villiers' "The Set of the Sails".
OR
Do an ocean passage on a 40 foot yacht with three people aboard. You WILL learn something.