The film is inspired by Robert Louis Stevenson's Treasure Island (1883) which is mentioned several times in the film by both John Cusack and Robert Loggia. Cusack is the young steward character and Loggia the captain of the ship character. The pirates in this case are the father and son team of Jerry Stiller and Ben Stiller, who are real life father and son. The damsel in distress is Wendy Gazelle, who plays Cusack's girlfriend in the film and who can be loosely claimed as being the treasure as well.
First big screen appearance of real life father and son Jerry Stiller and Ben Stiller together in the same movie who actually do portray a father and son. The pair also collaborated together in two shorts the same 1987 year: Shoeshine (1987) and The Hustler of Money (1987).
The name of the educational institution was the "Burnham Preparatory School for Boys". This was actually in reality portrayed by the real-life St. Michael's University School in Victoria, British Columbia, Canada.
According to the book "My Life as a Mankiewicz: An Insider's Journey Through Hollywood" (2012) by Tom Mankiewicz, Anthony Michael Hall was considered for the lead role of Dan Bartlett which in the end was cast with John Cusack.
Star John Cusack, who appeared in a number of 1980s teenpics, later on went on to revisit the genre about twenty-three years later after this film, with Hot Tub Time Machine (2010). Both of these two pictures have titles which are prefixed with the word "Hot".