As of this episode, the Simpsons have been on all seven continents.
The episode title refers to "A Supposedly Fun Thing I'll Never Do Again", an essay by David Foster Wallace, about his experiences on a vacation cruise.
The cruise ship the Simpsons travel on features go-kart racing. When this episode first aired in 2012, no actual cruise ship featured go-kart racing. In June 2017, the Norwegian Joy became the first cruise ship to feature go-kart racing.
The episode's sub-plot references a real life incident on a Carnival cruise ship in Febuary 2013 when an engine fire stranded the ship out at sea for five days.