When his travels take him to rural Hokkaido, Tora-san helps a cantankerous old veterinarian (Mifune) in his relationships with his estranged daughter, and a woman in whom he is secretly interested.
Traveling salesman Kuruma Torajirō falls in love with an inn manager as New Year's approaches.
Taking a message from Hiroshi's father to heart, Torajiro attempts to give up his wandering ways.
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.
After a quarrel with his mother, Torajiro sets off to find a bride.
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.
While Sakura and Hiroshi struggle to save funds to build a house, Torajiro befriends three young women on vacation during his travels.
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.
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.
In Shibamata, Tokyo, Tora-san's family prepares for a wedding. Meanwhile, the traveling Tora-san meets an old acqaintance in Iwate Province. Tora-san refuses to drink with him, afraid that the acquaintance, now settled and married, will again become attracted to Tora-san's wandering existence. Tora-san becomes attracted to a female barber, but must break off their relationship so that she too can live a secure life. She instead gets into an abusive relationship with a motorcyclist.
In Nagasaki, Tora-san and an acquaintance help an old woman who has fallen and injured herself. She invites them to her home where the three share a night of eating and drinking. The old woman's health deteriorates and she dies. At her funeral, Tora-san falls in love with the old woman's daughter, but winds up acting as a go-between for her and a young law student.
Tora-san's family's neighbor, Akemi, who had been married in Marriage Counselor Tora-san (1984), runs away from her husband, who is only interested in work. Tora-san follows her to Shikinejima, and attempts to bring her back to her home. In doing so he encounters a school-reunion group who are traveling to meet their elementary school teacher, which is a reference to the film Twenty-Four Eyes by Keisuke Kinoshita. Tora-san joins them and falls in love with the teacher.
During his travels, Tora-san comes across a traditional theater he used to visit, and discovers that one of his old friends has died. Tora-san and his family help the friend's daughter, who becomes romantically involved with an aspiring artist.
A playboy-gambler friend of Tora-san’s dies and, abandoned by his mother, his little boy suddenly turns up in Shibamata. Searching for the boy’s mother, Tora-san meets a cosmetics saleslady and the three become a surrogate family, with Tora-san as “daddy”.
In his travels through Japan, Tora-san meets and falls in love with a female doctor, however he is afraid of committing to a relationship.
During his wandering throughout Japan, Tora-san meets a suicidal man. He travels with the man to Vienna, but winds up homesick for Japan.
Mitsuo goes to Nagoya to visit Izumi, whose father left Izumi’s sad, bar hostess mother for another woman, so together they decide to confront him in Oita. Meanwhile, Izumi’s mother befriends Tora-san and together they travel to Oita to meet them, with Tora-san quickly falling for her en route.
After failing to find a job, Mitsuo becomes a fisherman on a small island, and develops a crush on a young nurse there. Tora-san, dispatched to bring Mitsuo back home, himself falls in love with an attractive but troubled woman visiting her father.