While Sakura and Hiroshi struggle to save funds to build a house, Torajiro befriends three young women on vacation during his travels.
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 visits Hokkaido and is reunited with Lily. Now divorced, she plans to resume her singing career and renews her unusual relationship with Tora-san.
Taking a message from Hiroshi's father to heart, Torajiro attempts to give up his wandering ways.
When Tora-san returns to visit his family, he is surprised to find an arrogant professor occupying his room. The professor and Tora-san become rivals for the affection of Chiyo.
Tora-san's opinions about Americans get challenged when another wandering peddler Michael Jordan stops by Shibamata.
After an encounter with a dying yakuza's son and at his sister Sakura's urging, Torajiro attempts to change his vagrant lifestyle and become an honest worker with a steady job.
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.
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.
Torajiro becomes homesick during his travels after watching a television report about his hometown and meeting a young woman that reminds him of his sister Sakura. Meanwhile, a new tenant moves into Toraya restaurant.
Traveling salesman Kuruma Torajirō falls in love with an inn manager as New Year's approaches.