After Torajiro's latest attempt to find a bride goes awry, he starts traveling again and runs into Utako (last seen in Tora-san's Dear Old Home), now a widow.

Tora-san befriends the descendant of a feudal lord. The man asks Tora to locate his deceased son's wife who resides somewhere in Tokyo.

Carrying a bag full of samples, Mitsuo makes rounds to shoe stores in remote cities. While staying at budget hotels, his thoughts turn to Tora-san.

When Tora-san's infatuation with his nephew's school teacher causes family turmoil, he leaves on his travels again. When he returns, he falls in love with the teacher's mother.

After Hiroshi is injured in a workplace accident, Torajiro gives Sakura the money he has saved and leaves to work as a traveling salesman once again. During his travels, Torajiro meets a father who shares a drink with him. In the morning, Torajiro is shocked to learn that the man has left his baby behind and a note asking Tora to take care of the child.

Tora-san visits Hokkaido and is reunited with Lily. Now divorced, she plans to resume her singing career and renews her unusual relationship with Tora-san.

Tora-san is inspired to pursue an education after a visit to the grave of a woman he met years ago. When he returns to Shibamata with the intent to study, he falls for Toraya's new tenant instead.

Tora-san's nephew Mitsuo is exchanging letters with Izumi, a former classmate whose parents divorced and took her out of Tokyo.

Tora-san leaves Shibamata once again after an argument with his family and finds himself at an inn where he meets Tomekichi, a young man who looks up to Tora-san.

When cabaret singer Lily writes Toraya about her illness, Tora-san rushes to Okinawa to be by her side.

After a chance encounter with Hiroshi's father on a bus, Tora decides to get serious and reflect on the mortality of man. His plans are derailed when a beautiful lady starts working at Toraya.

Tora befriends a pretty barbershop owner and runs into Izumi. When Tora twists his ankle, Mitsuo comes to care for him and see Izumi. Meanwhile, Izumi must choose between her new job in Tokyo and returning to Nagoya to care for her mother.