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.

After a tumultuous night in Ibiza, Rob and Jess struggle to reconcile. A mechanical error during docking has Captain Sandy scrambling to avoid a catastrophic disaster, while the new charter guests arrange a bet with Bugsy that threatens to disrobe the crew. Meanwhile, a guest request sends a sleep-deprived Tom over the edge.