With Hannah's back against the wall, Captain Sandy faces a difficult decision that could change the trajectory of The Wellington. Bugsy grapples with a new challenge, while Malia worries about Tom's ability to navigate a chaotic first charter.

Baseball legend Johnny Damon returns to charter in Ibiza, putting pressure on Tom to rectify the Damons' poor experience with the food they were served last season. With Aesha onboard, Bugsy ups her expectations for the interior team. Meanwhile, Rob's personal life begins to interfere with his work, and Jess notices some red flags with his behavior.