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. Ben redeems himself after the previous night's Moussaka mishaps. Bobby crushes on Julia, and meanwhile a homesick Jen feels like she's getting assigned all of the tedious tasks by Bryan and is being underutilized. 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 for their upcoming calendar shoot, the Ionian Princess crew struggles to keep up with their demands. As the crew assist the charter guests with their photo shoot, 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 in England, while Bobby's feelings for her grow stronger. Ben and Hannah's work relationship has reached smooth sailing, while 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.

After Ben apologizes for shutting down Bryan and Tiffany's fun, the crew prepares for their next charter hailing from Oklahoma. The stews are tasked with putting together a country hoedown complete with bales of hay. 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.

Hannah feels betrayed when Ben goes to the Captain about their galley miscommunication. The Crew finally enjoys a day off until Bryan gives Danny an etiquette lesson. An all-male charter group has Danny and Bobby finding them arm candy in Mykonos.

Hannah's migraine explodes when the charter guests bring back a large group of girls on board. Upon their exit, the bachelors anoint Danny as the charter MVP, much to the chagrin of Bobby and Bryan. And, Danny continues to lose the respect of his crew by breaking yet another yachtie code and inserting himself into Hannah and Ben's business.

Hannah and Ben redefine their relationship, while Bobby realizes he can't shut off his feelings for Julia. After the crew pulls off a beach BBQ, Ben has to make American S'mores in Greece. And Bryan confronts Julia about not completing her duties.

While Danny is away at the hospital, the crew revels in his absence; Jen finally stands up to Bryan; Tiffany's feelings for Ben increase; as one easy-going charter leaves, the crew is blind-sided by a new group of highly demanding guests.

The demanding charter guests extend their stay, and Hannah puts on her best stew face to regain their trust. Julia and Ben have a class war after a miscommunication goes awry. Meanwhile, the Captain gives Danny his phone back, putting Bryan on high-alert. And Ben's friendship with Hannah deepens when he confides in her about his deep-seated issues.

As the guests finally prepare to leave the yacht after their extended stay, Hannah hopes her charm wins them over with a generous tip. Meanwhile, Captain Mark is left with a big decision that will shake up the dynamic of the entire crew after things escalate between Danny, Bobby, and Bryan. On the crew’s night off, Ben and Tiffany take their flirtation to the next level, unbeknownst to Hannah. And Bobby’s plan to bring a date back on the boat backfires in more ways than one.