Captain Lee, Kate, Ben, and Kelley are joined by new crew members as they prepare for a new charter season; Kate finds herself shorthanded after a junior stewardess misses her flight; Kelley has his hands full with headstrong deckhand Trevor.

Kelley makes a decision on how to proceed with Trevor. The new charter guests prove to be a handful with a very pampered poodle. Ben and Kate clash again, while Kelley continues to deal with Trevor's poor attitude. Meanwhile, Kelley gets a call from a loved one and Trevor proves old habits die hard during the crew's second night out.

Trevor faces the wrath of Captain Lee after putting the crew's safety in jeopardy during their night out. Ben stresses over a charter guest with very particular dietary needs. Kelley and Nico both find themselves attracted to the same Stew and Sierra learns just how difficult it can be working with Ben.

Sierra makes a decision following a tense night with Ben. Kelley is challenged with getting through the charter shorthanded. A new crew member joins Valor. Nico takes his pursuit of Emily to new lows but will it cost him his friendship with Lauren?

Captain Lee grows increasingly frustrated with Kelley after a series of missteps by the newly minted bosun. Kate is surprised by a visitor that rattles Ben's ego to the core. Kelley steps up his game in his pursuit of Emily. Meanwhile a terrifying boating accident leaves the lives of the charter guests hanging in the balance.

Kate says goodbye to her girlfriend Ro while Ben makes a heartfelt gesture to a fellow crew member. The stakes are high for the Valor crew as they have to prepare the perfect surprise engagement dinner for two of their guests. Captain Lee’s patience begins to wear thin as Kelley loses control of his deck team. Kyle takes his admiration for Sierra to the next level.

Kelley is angry with Sierra after he finds out how she treated a member of the deck team. Emily enjoys a night out with Ben while things get very heated between Kate and the exterior crew. Kyle puts on the charm when he gets his wish and takes Sierra out on a date, but things don't go exactly as planned.

The Valor crew welcomes aboard a new group of guests, while Ben and Kate have it out over another miscommunication. Emily is upset after Ben embarrasses her. Nico is unimpressed with Kelley's inability to manage his team.

Sierra loses her cool after Kyle pushes her patience to the limit. Ben's latest galley masterpiece ends up having a near lethal effect on one of the crew. Kyle finds a common bond with one of the charter guests and introduces the crew to a new side of him while Ben and Emily take their relationship to the next level.

Captain Lee reprimands the crew for damaging a very expensive piece of the boat; Nico confronts Kelley; Dean Slover returns for a third charter trip; Kelley's managerial skills are put to the test when Dean throws a curve ball.

Kelley suffers the repercussions of stranding Dean on an isolated beach. Captain Lee makes a decision regarding the exterior team that shakes Kelley to his core. Kate grows frustrated with Emily's lack of attention to her job. Ben and Emily take their relationship to the next level and Kyle must decide whether or not to tell his girlfriend about his date with Sierra.

Kate's patience grows increasingly thin with Emily and Sierra's work ethic. Sierra and Kelley have heated words. Kelley acclimates to life onboard with a new Senior Deckhand and Lauren and Nico grow tired of Kate's manipulative ways.

Sierra spirals out of control. Emily questions if Ben is truly "just friends" with Kate. Kyle makes Ashley a very attractive offer. Kate sits Nico and Lauren down for a one-on-one chat and Ben crosses a line with Kate that changes the dynamic of their friendship forever.