The Simpsons join other Springfield families on the Van Houtens’ annual trip to Costa Rica, where Homer befriends Patty’s new girlfriend and Lisa discovers how the Van Houtens are able to afford this trip every year.
Marge becomes a competitive lumberjack and goes on a month-long retreat to Portland with her trainer, whom Homer fears will take his wife away from him.
After a trip to Aquatraz Water Park, Lisa becomes determined to set free Springfield's most vicious animals in captivity. Meanwhile, Homer fulfills a lifelong dream of buying a boat, and quickly realizes boat ownership sucks.
Horrors include a demon Maggie, a mission to rescue Milhouse from another dimension, dead-Homer’s spirit trying on some new bodies for size, and Selma finally finding love in an unlikely place.
When the wrong man is arrested for pickpocketing Springfield during the San Castellaneta street festival, Chief Wiggum sets out to catch the real criminal.
Homer is demoted to supervising interns, among whom is go-getter millennial Mike, a 35-year-old who asks Homer to be his mentor. However, when Homer inspires Mike to start a business of his own, the two find themselves being chased by the mob.
When a video goes viral of Bart and Homer fighting, they begin a journey as social media celebrities. Meanwhile, Lisa battles the school’s new industrialized detention system.