Jake comes face-to-face with his old nemesis Doug Judy as he and Amy go on a cruise. Meanwhile, Holt's sister comes to town for a visit, and Diaz and Boyle fight over a rent-controlled apartment which was a crime scene.
Jake and Amy are excited to go on their first real vacation together, but Amy's perfectly planned cruise ship itinerary is thwarted when they discover an old adversary is on board with them. Meanwhile, Gina and Terry help Captain Holt survive a visit from his sister, Debbie, and Charles and Rosa vie for the same apartment.
Jake wins two tickets to a cruise without entering a contest, and brings Amy along with him. Once aboard, they realize why they are truly there. Meanwhile, Captain Holt's sister, a total drama queen, visits. Rosa and Charles fight over an apartment only made vacant because the tenant was murdered.