In On the Town, three sailors—Ozzie, Chip, and Gabey—arrive in New York City with just 24 hours of shore leave and a mission: see the sights, find romance, and make the most of every minute. Chip follows his trusty guidebook, Ozzie pursues every pretty face in sight, and Gabey falls head over heels for a subway poster beauty, "Miss Turnstiles" Ivy Smith. The trio scatters across the city, igniting a whirlwind of comic encounters from the Museum of Natural History to the backseat of a taxi.

As night falls, misunderstandings multiply and a parade of police, professors, and fiancés chase the sailors through Manhattan. When Gabey finally finds Ivy at Coney Island, chaos erupts and dawn arrives all too soon. With forgiven hearts and fleeting romances, the sailors head back to sea—just as a new trio arrives, ready to paint the town all over again.