If Milton Bradley were a medieval company, they'd never have called it "The Game of Life." Instead of a car marker, you'd use different pilgrim's symbols, a sea shell for St. James Compostela, a key for Rome, a cross for Jerusalem.
Instead of going to college or getting married, you'd meet up and see how long Fellowship stuck around; then you'd see how long your worldly goods helped. And there'd be progressively less explanation, because by the end of the game, you either get it or you're going down. You could have a fiery pit going for anyone who didn't "win" and watch their little symbol burn to a crisp!
Maybe we could make it into a mmrpg! WOW watch out! Think of the fun. Think of the quests.
You'd go up to the old looking dude with the red exclamation point over his head at the beginning of the game, and off you'd go. We could even have the protestant version with a Spenser zone, where you slay the printing press dragon and beat Orgoglio, and then face off with the Blatant Beast!
I need to get a life.