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.

Capt. Lee invites a special guest to come aboard; the crew is surprised by a familiar face; an all-female charter proves to be a handful for Kate and Capt. Lee; as Matt continues to struggle, Capt. Lee takes action to prevent further embarrassment.

Capt. Lee tests Matt as he removes Bruno from the galley and joins the women for dinner; Jen and Kate's working relationship deteriorates; Kyle and Jen grow closer, but Kyle has ulterior motives; Jen reaches her breaking point.

Timothy Sykes comes back and cannot function without his Wi-Fi, which causes pressure for Kate and Captain Lee. Jen is closely followed after upsetting the entire crew. Nico must make a tough choice about his relationship.

Tensions within the crew run high on the final night of the charter season; Timothy Sykes micromanages the crew; Jen tries to be on her best behavior; Nico summons the courage to end things with Brianna; Jen attempts to mend things with Kate.