Tension is high as Kate and Nico continue to struggle operating with a crew of newbies. New personalities bring new challenges as the crew welcomes their first charter guests - a group of self-proclaimed "adrenaline junkies." Mistakes continue to follow the crew and Captain Lee finds himself having to get more involved in troubleshooting the problems. Meanwhile, Brianna becomes the object of everyone's affection and later during their first night out, the alcohol flow reveals some of the crew's true colors and romantic intentions.
Chris Brown's decision to nap during work hours finds him in the crosshairs with Captain Lee. Kate puts her stews through 101 training in order to get them ready for their next charter. The new guests prove to be a handful with indestructible livers and put the stews' new training to the test. Kate meets a cute sailor she nicknames Jesus and has a midnight rendezvous on his boat during charter. Matt faces his first challenge of the season with sushi dinner and a tequila pairing while Bruno steps up to the plate by dressing down in his skivvies to impress the guests.
During their night off Jesus and Kate get to know each other while Chris Brown makes a pass at Brianna. Nico deals with the stress of the boat on the 3-month anniversary of the passing of his younger brother. Meanwhile a group of eight fun charter guests arrive ready to party down which proves a challenge for Kate and the interior. Matt makes a move on Brianna while Nico's wandering eye might end up getting him in trouble with his girlfriend back home. Nico and the exterior make a disastrous mistake during un-docking.
As Charleston reels over Thomas’ arrest, a distraught Kathryn deals with conflicting emotions and the possibility of getting full custody of her kids. Cameran learns you can’t have it all as she struggles to balance motherhood and her career, while Naomie has no issues juggling a hunky new boyfriend and a thriving new business Craig, got his groove back after a summer stint in the Bahamas this summer, while Austen was caught in a compromising position. But as everyone gathers at Patricia’s dinner party, it’s another secret romp that has everyone shocked.
Cameran gives Eliza an earful about her brash behavior at Patricia’s dinner party. Austen and Craig meet Whitney for lunch, he is in the hot seat over some rumors of his current relationship status. Meanwhile, Kathryn and Chelsea settle into new homes. When Chelsea hosts a house warming party to show off her new digs, Cameran spills the beans on Whitney and Kathryn’s secret liaison.
Cameran continues to struggle with being a stay at home mom, while Naomie juggles her burgeoning clothing company and her family’s restaurant empire. As Kathryn opens up about her new boyfriend, Craig becomes the resident town gossip, spreading rumors not only about Kat’s new man but Austen’s girlfriend. When Shep hears the rumors, he and Craig go on the offensive to try to protect their friend.
Austen has second thoughts about breaking up with Madison, but he has bigger problems when Chelsea learns he's been badmouthing her around town. Meanwhile, a shocking experience gives Eliza a new lease on life. After Kathryn pulls another one of her MIA stunts before the girls’ trip, Danni and Naomie insist on holding her accountable.
Kathryn and Danni leave the girls’ trip on frosty terms, as Cameran realizes she needs to get back to work. Meanwhile, Craig is way behind on pillow orders and decides to host a party to trick his friends into helping him sew. The party takes a turn for the worse when Chelsea lays into Austen for talking behind her back, and Kathryn and Danni confront their friendship issues head on.
The group decides to take a trip to Colorado to help Cameran rediscover her mojo. Naomie refuses to go because she doesn't want to spend a long weekend with her ex, Craig, and his unresolved feelings for her. Meanwhile, Eliza hosts the gang out at her family's plantation for a day of skeet shooting and invites a blast from the past, which backfires big time.
As Charleston deals with the fallout from Ashley's "apology tour" at Eliza's luncheon, Kathryn confronts Whitney about their summer romance rumor. Cameran reveals to Shep that she’s invited Madison, to her birthday ski trip in Colorado, much to his chagrin. Meanwhile, the trip gets off to a rocky start as a frustrated Craig unleashes his pent up fury on the gang. As everyone settles into the Steamboat Springs chalets, all eyes are on Austen and Madison as they spend their first night together under one roof since their breakup.
Chelsea, Cameran, Eliza, Danni and Kathryn hit the slopes for their first ever ski lesson, while Craig, Austen and Madison snowboard. When Austen and Madison’s relationship starts to heat back up, Kathryn reveals more dirt on her hook up with Whitney. Later, tensions rise when the gang enjoys a cannabis infused dinner, and Kathryn is confronted with her past mistakes. Meanwhile, back in Charleston, Naomie gets an unexpected phone call from Ashley.
After a raucous night in Colorado, Cameran and Whitney decide to hightail it back to Charleston while the rest of the gang hits the hot springs. When it becomes clear that Austen and Madison’s road to reconciliation won’t be an easy one, Shep gloats. An infuriated Madison repeats a rumored secret that not only throws Shep under the bus, but Danni too. After this bomb is dropped, Austen is left to pick up the pieces, and the rest of the Charmers to take sides.
Shep’s ultimatum to Austen is tested after he and Madison reconcile. Meanwhile, Ashley resurfaces asking for a ‘second’ second-chance, which Eliza obliges with an invitation to her Fox Hunt. When Ashley and Kathryn come face-to-face for the first time in a year, the gang prepares for the brawl of the century.