Inferno

In Dante's Inferno, the Roman poet Virgil guides Dante through Hell (and, later, Purgatory), showing the various circles of Hell and some of the residents thereof. Dante's Inferno is a sim that recreates that journey, down all nine circles, with notecards describing each stop. And then one climbs back again through a fictional story set in modern times, with each stop recreating one of the sins of the accompanying circle. Very educational.

My knowledge of the Inferno came from the Larry Niven/Jerry Pournelle book of the same name, so it's possible my recollections of the place were warped by a pair of 20th century science fiction writers.