The first charter of the season is underway, and Chief Stew Jenna is already feeling the pressure as she is tasked with planning an impromptu wedding for two drunk guests. First Mate Paget is trying to keep his cool and patience with his new deck team, including Ciara, his girlfriend of four years. Parker, an inexperienced deckhand, struggles to adjust to the posh world of yachting. Meanwhile, Captain Glenn attempts a risky maneuver while climbing the mast to fix a broken sail. During the first night out, two yachties have a steamy interaction that quickly makes their professional relationship personal.