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.
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.
Tora-san's opinions about Americans get challenged when another wandering peddler Michael Jordan stops by Shibamata.
Tora-san spends several days at the home of a hard-working salaryman ("salaried worker"), who abruptly disappears. When the man's wife asks Tora-san to help find him, he falls in love with her, and secretly hopes the husband will not be found.
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.
Mitsuo, unhappy in his new job as a shoe salesman, is invited to a festival and is introduced to a friend’s sister. Tora-san meanwhile helps an injured housewife on her yearly vacation.
Tora-san works hard to bring together his nephew, Mitsuo, and Mitsuo’s girlfriend who is engaged to someone else.
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.
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 a friend and business colleague dies, Tora-san visits the man's daughter, then takes her to Tokyo so she can study for a night school exam.
When his travels bring him to Osaka, Tora-san falls in love with a local geisha. He helps her to track down her estranged brother, and informs his family that he plans to marry her. His plans are foiled when the geisha informs Tora-san that she is engaged.
Tora-san returns to his family's home to attend an elementary school class reunion. After he embarrasses himself by getting drunk and insulting all his ex-classmates, he resumes his travels. In Kyushu he meets an outspoken 18-year-old girl who becomes enamored of Tora-san and follows him around. One of Tora-san's old friends is terminally ill and makes Tora-san promise him to marry his wife once he is gone.