Captain Sandy embarks on another season in the Mediterranean out of the world famous yachting hub, the French Riviera. Hannah returns as chief stew determined to put her head down, focus on her work and her relationship with Captain Sandy. After enduring heartbreak, Joao returns with a promotion as Bosun hoping to prove to Captain Sandy he can lead a deck team that includes his best friend and partner-in-crime, Colin. Cordon Bleu trained chef Mila takes control of the galley, but immediately falls ill on day one, forcing the crew to rally and help get the boat in shape in time for the first charter. When the first guests arrive and chef Mila, who is a department of one, is still battling illness, Sandy and the crew wonder if she'll be able to perform her most basic duties.

The Sirocco crew comes to terms with Mila's controversial views. Captain Sandy's good friend, Dr. Jennifer Berman, returns with the expectation of actually leaving the dock this year. Hannah's on high alert making sure Sandy's friends are taken care of and Sandy's toast is butter free. Meanwhile, Joao continues to struggle to motivate Jack. Colin wonders if this new crew might be a little too bawdy for him, and Chef Mila's redemption charter gets off to a choppy start forcing Sandy to think outside the box with a unique plan.