Join Chef Ben Robinson and eight new crew members as they prepare the Ionian Princess, for a new charter season around the Greek Islands. Fresh faces present new challenges as the crew learns to work and live together while preparing to welcome their first guests. Bosun Bryan gets an unexpected promotion, while chief steward Hannah has her hands full with her ambitious third stew. Trying to meet the guests' one non-negotiable, they run into an unforeseen obstacle: streaming a live football game in the middle of the Mediterranean.

The crew's effort to stream a football game in the middle of the Mediterranean doesn't go as planned, but their efforts don't go unnoticed by the charter guests. Bobby crushes on Julia, and Jen feels like she's getting assigned all of the tedious tasks by Bryan. And after staying up all night with the Primary's husband, Tiffany breaks down after Hannah confronts her for not finishing her duties.

After the crew's first night off, Hannah puts her foot down when Bobby and Danny bring girls back to the yacht. Bryan attempts to smooth things over with the captain, but the boys are given their first strike. When an all-female group charters the yacht, the crew struggles to keep up with their demands. Danny breaks yachtie rule number one and drama ensues.

Danny disobeys a direct order from Captain Mark when he decides to give a love poem to a charter guest. Julia calls her boyfriend, while Bobby's feelings for her grow stronger. Tiffany works harder on her stew skills in hopes of Hannah noticing. On their night off, Ben is torn between two stews, but is shocked when he finds one of them in his bunk with Bryan.

The crew prepares for their next charter hailing from Oklahoma. The stews are tasked with putting together a country hoedown. Meanwhile, the deck crew unravels when Danny accuses Bobby for not being part of the team. After hours, the charter guests seem to have a threesome in the jacuzzi and once again, Danny is in hot water for overstepping his boundaries.

New charter guests come aboard to celebrate their seven-month dating anniversary, and the crew must provide the romantic trip of their lives. Ben takes Hannah on a date, but a major galley miscommunication during the guests' dinner could tarnish any romantic hope for the two. And, when a nearby vessel begins to sink, the Ionian Princess crew has to spring into action to help save it.