Tony Spear, an irrepressible, carefree sailor, returns home to the United States after years of roaming the Orient with his loyal crewman Corky Nye. His father, R. D. Spear, a wealthy department-store owner, and his brother John Spear brace for the impact Tony could have on the family’s steady, respectable reputation, remembering the last time he caused a stir.
Back at the store, John reveals big news: he has just proposed to Jo Spiggins, a trusted employee who grew up with them. Jo, now a valued member of the shop, seems happy with John at first, and Tony is initially pleased too. However, Jo's father, Spiggs Spiggins, a store manager and classmate of R. D., does not think John is a good match for his daughter and would prefer Tony as a son-in-law. When he sees how much happier she is after going out with Tony, he tries to get Tony to marry Jo himself.
As time passes, Jo warms to Tony, and the two look forward to a future together. Then a diving exhibition changes the mood: Tony invites two female friends and their dates to their table; he drinks too much and dives off the board in formal evening clothes. Jo, unsettled, stalks off. When Tony runs after her, a scuffle erupts and he ends up jailed. Amid the bustle, Jo accepts John's proposal, tilting the balance of their future.
Determined to block the match, Spiggs hatches a plan: he drinks to excess and hides out on Tony's sailboat, the Vagabond Lady, hoping that without a proper wedding escort Jo cannot go through with it. Jo tracks him down and misreads the situation, assuming Tony is the one sabotaging the wedding. To buy time, Tony offers to sail Jo to the wedding in Westport, with Corky along for support.
On the voyage, Tony warns Corky to throw him overboard if he lays a finger on Jo. Corky, also drunk, teams up with Spiggs, and a storm rises. Tony must rely on Jo to help navigate the rough seas, and the two share moments of tension and connection as they work together. They quarrel briefly, then kiss, a moment that changes everything. The next morning, Corky recalls only a hazy memory and tells Jo that Tony has a habit of leaving him to deal with women.
Jo, swayed by Corky’s tale, believes him and decides to go through with the wedding to John. Yet Tony—who has somehow commandeered a fishing boat—arrives just in time to persuade his brother that Jo would not be respectable enough for his career and reputation. Jo, however, is delighted to be with him, and Tony drags her away, sealing their union in a bold, romancing finale.
